What is your ideal vacation? Does it involve spending quality time with your family, friends, and/or significant other? Does it involve, literally, separating yourself from your mobile device in every sense of the word? Which includes, resisting the scanning of your work emails, spending less time scrolling through your favorite social platforms, including scrutinizing pop-up news articles? Or, perhaps, your ultimate vacation simply involves a much-needed mental break from, dwelling on the New Year’s resolutions you have yet to accomplish, and grudgingly crafting a mental to-do list for the week…?
Nevertheless, whatever your perfect get-away entails, it’s worth spending your well-deserved and well-earned time in a place with as much character and as much culture as your own. A place that will, poetically melt your mind’s ‘metals’, so to speak, and loosen your bonds to reality. What better place to sit and soak in the history of the land, the sacred culture, and absorb the nautical nature, than Martha’s Vineyard. An island off the southern coast of Massachusetts mainland, with over ten thousand years of stories and legends.
Legends has it, the Wampanoag tribe, who inhabited the island thousands of years before the first European explorers, believed that a benevolent giant, with supernatural power, named Moshup, is responsible for shaping the Vineyard. Which at the time, was known as the island of Noepe, meaning, ‘Land amid Waters’. Moshop, weary from his journey across the island, dragged his foot in the mud leaving a deep track, in which the ocean gradually saturated through, hence creating the island of Noepe.
Years later, the island acquired its modern name, in 1602, when British explorer, Bartholomew Gosnold, renamed the island, Martha’s Vineyard, after his daughter. To this day, the entire Vineyard, especially the cliffs of Aquinnah, remain sacred in the hearts of many Wampanoag people, who still reside on the island, and in the hearts of both locals, born on the island, and ‘washashores’, those who were not born on the island.
So, disguise yourself as a local, with an eye for exploration, alongside this comprehensive guide to Martha’s Vineyard. One of those perfect vacation places, where you can find plenty of engaging activities, but, on the flip side, you could also do much of nothing, and feel perfectly satisfactory. Each seafaring town has something unique to offer.
The following guide is organized into six categories: Vineyard Haven, Oak Bluffs, West Tisbury, Edgartown, Chappaquiddick, Chilmark, and Aquinnah, with subcategories in each, which include, but are not limited to: Reserves, Sanctuaries, and Conservation Land, Parks, Beaches, Activities and Sports, Farms and Farm stands, Architecture and Sightseeing, Art Centers, Museums, Shops, Restaurants, and Breweries. Entries under the subcategories are in no particular order, however, there are links to every place listed with a small write-up, detailing why every single location is uniquely worth the visit. I hope this guide both educated and inspires.
To places near and far, to destinations you thought were a dream, to escaping reality, to your next get-away, cheers!
VINEYARD HAVEN:
Wildlife Refuges, Sanctuaries, and Conservation Land
Manuel F. Correllus State Forest
At the center of Martha’s Vineyard, this five-thousand-acre forest, has miles of trails for walking and , hiking and has paved shared-use paths for biking. Plus, two hidden gems within the forest, include a secret disc golf course and a statue honoring the heath hen, a type of grouse what went instinct in 1932. Can you find both? Park for free in lots of Barnes Road and Old Country Road and find out for yourself.
One of the many Land Banks on the Vineyard, great for studying nature, hiking, picnicking, and dog walking. Wilfred’s Pong Preserve is a scenic costal pond, bordering the sea, separated by a barrier beach. Islanders created the Martha’s Vineyard Land Bank Commission in 1986, which now has over three thousand protected areas under its jurisdiction. Land banks are created by local jurisdictions, usually as a public entity, to hold and conserve properties that had previously been abandoned, vacant, and tax-delinquent. Land bank properties are open daily to the public from sunrise to sundown, except during hunting season.
Activities and Sports
A highly reviewed, natural water sports equiptment rental service, with kayaks, sailboats, canoes, windsurfers, and various gear, available in their Vineyard Haven store front. Furthermore, they offer windsurfing, paddle boarding, kayaking, and sailing lessons.
Travel
High speed, year-round, ferries to and from Cape Cod and Martha’s Vineyard, and Nantucket. Travel between Woods Hole and Hyannis terminals to the Martha’s Vineyard and Nantucket terminals. The Marth’s Vineyard steamship terminal is located in Vineyard Haven. View their website for ferry schedules and rates.
Lighthouses
Established in 1817, West Chop Lighthouse defines the harbor of Vineyard Haven, along with East Chop Lighthouse. West Chop lighthouse was automated in 1976, the last of Martha’s Vineyards’ lighthouses to lose its resident keeper. The light house is not open to the public, but remains to actively aid navigation, and currently serves as Coast Guard housing.
Farms and Farmers Markets
Island Alpaca Company of Martha’s Vineyard
A year-round farm, with over fifty colorful Huacaya alpaca on an expansive piece of property. Interacting with the alpacas in encouraged upon visiting. They also offer alpaca breeding, sales, boarding, and education. Round out your unique experience, by visiting their barn gift shop, packed with quality alpaca products.
Museums
A historical and cultural museum focused on inspiring visitors to explore and strengthen their connection to Marth’s Vineyard and the island’s uniquely diverse heritage. Founded in 1922 and originally named the ‘Dukes County Historical Society’, the museum was renamed to better focus on collecting the history of the island. Exhibit highlights include the original Fresnel lens from Gay Head Lighthouse, a display on shipping, navigating, and lifesaving, a hands-on history room for kids, and a display revealing larger artifacts in their collection, including, but not limited to, a peddler’s cart used for deliveries at Alley’s General Store, whaling vessels, the original hearse from Edgartown, and more. Visit their website for current, online, and upcoming exhibitions.
Playhouses
A year-round live theater in Vineyard Haven’s cultural district, presenting a selection of classic and contemporary plays. They also have art and drama classes for children and adults, along with other types of occasional programming and events in their historic theater, which dates back to 1833. Check out their seasonal schedule and what is currently playing through their website.
Shops
A forty-year-old, independently owned bookstore on Main Street, with a carefully curated selection of books and sidelines. They also host author talks year-round.
A boutique, located on Main Street, selling local and international housewares, such as luminaries, glassware, soaps, linens, ceramics, pottery, and art from local artists.
A gift shop on Main Street, packed with island-made and island-inspired products, trinkets, gifts, clothes, jewelry, homewares, puzzles. There is truly something for everyone in this shop!
A clothing retailer, founded by Captain Bob Douglas, over fifty years ago, which started as the Black Dog Tavern, a restaurant. The tavern’s signature graphic element, a black dog, became so popular, it is now a world-wide recognized symbol, featured on their apparel and goods. This particular store, in Vineyard Haven, is the first of many Black Dog stores, opened in 1992.
An upscale, costal, and casual island store, selling popular brand name clothing, plus swim, surf, and skate selections, founded by Elaine Barse in 1994. Elaine was also a founding member of the Martha’s Vineyard Skate Park.
A metropolitan and New England style, curated boutique, selling apparel, accessories, gifts, home, and decorative décor and art.
Restaurants, Cafes, and Bakeries
A highly rated and reviewed, made-from-scratch, espresso bar, café, and bakery with a Brazilian flair, started by a husband-and-wife chef duo. They also specialize in catering for wedding and events on the Vineyard.
Pies, pastries, breads, custom-made cakes, homemade-ice cream, gluten-free options, this bakery, and café has all the tasty treats.
A take-out counter bakery and farm serving breakfast classics and locally sourced dishes from their Bakehouse farm. They also make traditional Scottish shortbreads and pies in homage to the founder Mrs. Isabelle Maxwell White, who migrated to the Vineyard from Pebbleshire, Scotland.
A small, but cozy, establishment, serving creative American diner food for all day breakfast and lunch, for seventy-nine years, since 1943, with an expansive menu. The Art Cliff Diner is one of the top-rated restaurants and ‘foodie destinations’ in Vineyard Haven.
Little House Café is located in Vineyard Haven and their bakery is located in Edgartown. The café has both outdoor and indoor eating in a cozy, refurbished, and classic Cape-style house. They are open year-round for breakfast, lunch and dinner serving soups, salads, sandwiches, baked goods, and delicious entrees.
Year-round waterfront dining, founded by Captain Bob Douglas, after an unsatisfactory meal and a stale donut on a cold day in 1969, left him wondering why the Vineyard did not have a year-round restaurant. He started sketching a gambrel-roofed building on a napkin. The locals shared his excitement for this new creation and helped construct the tavern in the harbor of Vineyard Haven. Today, they serve favorites, such as omelets, pancakes, chowder, and seasonal entrees, for breakfast lunch and dinner. Don’t forget to visit their General Store for merchandise and their bakery for tasty treats.
Pan-Asian house and sushi bar, serving sake cocktails, and open six days a week for dinner, attached to the first floor of the Mansion House Inn. Most of the menu items are made in house and dishes are served family-style.
OAK BLUFFS:
Parks
An iconic seven-acre scenic park, with a gazebo in the middle, overlooking a vibrant neighborhood of Gingerbread houses, the ferry terminal, and across the street, the north Atlantic Ocean. A great place to stroll, jog, or walk your dog, have a picnic, fly a kite, look at the architecture, or simply relax.
Sightseeing and Architecture
Oak Bluffs Camp Meeting Association
Also known as the Gingerbread Cottages of Martha’s Vineyard, these vibrant houses are characterized for their whimsical Carpenter Gothic style architecture, known for its arched windows, board and batten siding, decorative bargeboards, and pitched roof. These quaint cottages started as summer tents for a group of Methodists that held annual religious retreats and meetings. As the meetings became more frequent, they built permanent cottages for year-round accommodations. Today there are three-hundred and eighteen cottages still on the island. Visit the Cottage Museum and Shop to view the interior of a typical Campground cottage and check out their Museum shop that has a wide selection of books, calendars, lanterns, and other Campground-related souvenirs and gifts.
The oldest platform carousel in the United States, constructed in 1876 by Charles Dare of New York Carousel Manufacturing, and incorporated in 1886 to the town of Oak Bluffs. To this day only two Dare Carousels still exist, the Flying Horses Carousel in Oak Bluffs and the Watch Hill Flying Hours Carousel in Westerly, Rhode Island. The Oak Bluffs carousel is open seasonally, starting on Memorial Day weekend and open throughout the summer.
Beaches
Inkwell Beach
A scenic public beach, stretching a little less than a hundred yards between the jetties, located across the street from Waban Park, and overlooking the hidden, yet, once most photographed, Lover’s Rock in the north Atlantic Ocean. The beach’s name ‘Inkwell’ supposedly both pejoratively referred to the African American visitors who would frequent the beaches shores and, at the same time, referred to the town’s prominent writers, who would mingle on the beach. Regardless of how the beach derivative its name, Inkwell beach is quite well-known and celebrated in the Vineyard and far beyond.
Joseph Sylvia State Beach
A scenic two-mile, sandy beach with calm and shallow water, overlooking Nantucket Sound on one side and the, four-thousand-acre watershed, Sengekontacket Pond, on the other side. This narrow beach runs along Beach Road, between Oak Bluffs and Edgartown, and was the setting for most of the beach scenes in the movie Jaws (1975). Above the bridge is the American Legion Memorial Bridge, more popularly known as the ‘Jaws Bridge’ or to locals, ‘Big Bridge’, connects Oak Bluffs and Edgartown. Joseph Sylvia State Beach is wonderful for swimming, walking, kiteboarding, and windsurfing, meanwhile, Beach Road makes for a scenic road trip.
BONUS: Here is a list of other Jaws (1975) filming locations on Martha’s Vineyard!
Activities and Sports
A kayak and stand-up paddleboard (SUP) rentals and tours. They also deliver equiptment, personal flotation devices (PFDs), and a handy map to all locations on the island…talk about convenient! Their priority is to educate those who paddle about the local environment and ways to protect and preserve it. They also offer a kid’s adventure tour and will work with you if, you are looking to host any type of beach party, from bachelorettes to business parties and everything in between.
Renting, selling, and repairing bikes since 1971, considered one of the best bike rental shops on the island. They also deliver for free around Oak Bluffs and most of the other surrounding towns with an overnight rental. They will also provide helmets, locks, baskets, bungee cords, and a map of the island.
Pirate Adventures Martha’s Vineyard
Sail along the shores of Oak Bluffs on a custom built forty-foot vessel called, the Sea Gypsy. Pirate Adventures is a memory-making, interactive pirate themed cruise fit for families, and designed for kids. Children can dress like pirates, assemble treasure maps, battle rival pirates with water cannons, and hoist sunken treasure. They also host oyster tours where families can learn where are how oysters are grown, meet oyster farmers and aquaculture educators. View their website for tour information and tickets.
Lighthouses
East Chop Lighthouse started as a semaphore station in 1828. In 1869, Captain Daggett built the lighthouse at East Chop, which was later destroyed by fire and then reconstructed. Still, residents felt like a proper lighthouse was in order, as many referred to Daggett’s lighthouse and dwellings as a ‘shanty’. Finally, in 1875 Congress approved the building of a light station at East Chop, which was constructed by mid-1877, as a forty-foot-tall conical tower. Captain Daggett’s dwellings still survives to this day and has been incorporated into a residence at the corner of East Chop Drive and Sandy Bluff Lane. Today, the lighthouse remains an active aid to navigation, and the land surrounding the tower was sold to the town of Oak Bluffs and used as a park. Meanwhile, responsibility for the lighthouse is in the hands of Martha’s Vineyard Museum. East Chop Lighthouse is open in the summer on Sunday evenings and can be rented for weddings.
Arts and Cultural Centers
Featherstone Center for the Arts
An art gallery with a mission to engage, enrich, and connect the Martha’s Vineyard community through art and creativity. They offer year-round educational programs and experiences for all ages, and strive to make art accessible to all. View their website for information on their seasonal events and exhibitions, plus get more information on their workshops and online classes.
Shops
A retail store in Oak Bluffs, Edgartown, and Vineyard Haven, selling comfortable sweatshirts, t-shirts, sweatpants, hats, and face coverings, all made from one-hundred percent cotton…soft as a grape!
A casual and high-end clothing and accessory retailer, started by brothers Shep and Ian Murray, who spent summers on the Vineyard. Both unsatisfied with their corporate jobs in New York City, they abruptly quit and had a vision to make neckties more appealing to New Englanders with whimsical and colorful patterns. To build their brand, they would travel along the eastern seaboard hoping to find customers interested in their merchandise. Today, Vineyard Vines has over a hundred locations worldwide.
Retail store selling apparel, sports gear, outdoor, and indoor games, hoping to spread the spirit of vacation to locals and tourists. Their logo, the lazy frog, represents the laidback feeling of the Vineyard. Now celebrating sixteen years, the Lazy Frog was started by a couple who began vacationing in Martha’s Vineyard back in 2003. The couple were playing a game with some friends, and made a comment that the shape of the island looks like a lazy frog, the rest is history.
A highly rated, eclectic retail shop and boutique, selling a wide range of jewelry, apparel, home accents, and souvenirs. A little-known hidden gem on the island.
An eclectic boutique, established in 1990, with an ever-growing and evolving, unique collection inspired by worldly travels. They sell children’s, men’s and women’s clothing, jewelry and other accessories, home décor, souvenirs, and more.
A small, seasonal and family owned retail boutique, opened in 2012, known for their signature designs featuring the Martha’s Vineyard secession flag of a seagull flying over the sun, as well as their own logo, nine dots, symbolizing morse code for the letters in their business’s name.
A seasonal and family-run boutique selling clothing, accessories, beach gear, home décor, hand-carved furniture, and souvenirs, all inspired by life on the Vineyard. They also have another boutique in Menemsha and a Coffeehouse and Restaurant and Bar in Oak Bluffs.
Restaurants, Cafes, and Bakeries
A highly rated and reviewed cozy coffee shop open daily in both Oak Bluffs and Vineyard Haven, serving organic, fair-trade coffee and espresso drinks, plus, homemade baked goods, some of which are gluten-free, and bagels.
A speakeasy-like donuts, fritters, and coffee shop with a little-known secret, that started in the summer of 1948, when the owner at the time would run the sales operations from the back door, and the tradition of Back Door Donuts was born. Today, they run sales from both the front of the shop, in the daytime, and then at night, locals and tourists, in-the-know, line up at the back door for late night treats. Be sure to inquire about their gluten-free donut options.
A quaint little restaurant, serving affordable options for all day breakfast and lunch, with a chef-driven menu, featuring local and seasonal ingredients. They also have vegetarian friendly options.
Both an outdoor café and an upscale dining experience with a seasonally changing menu, serving classic New American dishes, using local ingredients with modern approaches. Open for brunch and dinner, with an extensive wine list for cocktail hour. Plus, they have a gorgeous outdoor patio that is lit up at night.
Indoor dining for lunch and dinner, plus, bowling! They offer ten lanes of ten-pin bowling and scoring software. Their goal is to make bowling fun for everyone. They have pop-up rails, portable ramps for beginners and for serious bowlers, join their off-season leagues. As for their dining experience, they offer everything from wings and gourmet pizzas to sirloin steak.
A bustling artsy and laid-back farm-to-table and sea-to-table, New American restaurant, open for dinner, seasonally, seven nights a week. They take pride in sourcing local and supporting organic farming.
Open since 1976, serving homemade comfort food at reasonable prices with speedy service, with a breakfast all day menu, bottomless coffee, and seasonal specials. There is a reason why this island favorite has been brining smiles to locals and visitors faces for over forty years.
The first and only, year-round brewery and pub serving lunch and dinner, both inside and outside, on their patio. Book a virtual brewery tour or take an in-hours tour and get to know their brewing process and check out their formation tanks. On the way out, sneak a peek at their extensive list of beers on tap; they brew everything from golden ales to stouts.
Extremely popular seasonal waterfront dining, serving pub food alongside seafood favorites, with a raw bar and an extensive cocktail list for both lunch and dinner. They are located across the street from the Steamship Authority Terminal, a great first stop after getting off the boat! Part of the Santoro Hospitality Group, check out their sister restaurants, Fishbones Bar and Grill, Oceanview Restaurant and Lounge, both in Oak Bluffs, and The Net Result in Vineyard Haven.
Martha’s Vineyard Chowder Company
This casual fish house and raw bar is the number one place to get chowder in the Vineyard, plus, at any given time, they have fifteen beers on tap. Upstairs is the five thousand square foot ‘loft’ game room, with six pool tables, darts, foosball, shuffleboard tables, and a full bar.
Ben and Bills Chocolate Emporium
Serving homemade, hard-serve ice cream, gelato, chocolates, and candies. Try their famous funky lobster ice cream, made with real lobster chunks.
Live music, entertainment, lawn games, food, and drink plus, as if that isn’t enough, a store and lounge with coffee, baked goods, snacks, drinks, and merchandise. They also make their own rum, a homage to the rich run history along the eastern seaboard. Nomans is named after Nomans Island, a six-hundred- and twenty-eight-acre rock off the coast of Martha’s Vineyard, was notoriously used as a stow-away for fun runners during Prohibition and used as a practice bombing range for the United States Navy, until 1996.
WEST TISBURY:
Wildlife Refuges, Sanctuaries, and Nature Reserves
A Vineyard land trust, originally a meadow that belonged to a sheriff in 1850, and the name stuck over a hundred years later. Two pathways, the Ruth and Ed Brooks trails offer views of Eel Pond and Nantucket Sound, and John Butler’s Mudhole. In particular, the Brooks Trail is known for its olfactory pleasures in the springtime.
A gorgeous park with scenic views and a little over a mile trail, next to freshwater ponds, streams, sandy beaches, cliffs, oaks, and beach groves. A wonderful example of the habitats that make Martha’s Vineyard so special.
The largest, publicly accessible property on the Vineyard, owned by The Trustees of Reservations. Kayak and standup paddleboard rentals are available late summer, and two-mile trails lead you through oak forest and savannah. A historic point of interest, is the one-room Scrubby Neck Schoolhouse on Middle Point Cove, currently used as storage for The Trustees.
A horticultural and botanical landmark developed by Polly Hill, legendary horticulturist, and devoted to the cultivation and study and preservation of plants, and the tranquil landscape. Today, over seventy acres are preserved under the nonprofit, American Public Gardens Association. View rare trees, shrubs from around the world, including local favorites, such as azaleas, camellias, hollies, rhododendrons, crabapples, magnolias, and so much more.
Beaches
Sandy beach, open to residents and renters only, with appropriate beach stickers, but worth mentioning, because of its tranquil nature and scenic views of Vineyard Sound. A hidden gem of a beach on the Vineyard, due to its unique views of the cliffs, which makes a great sunset watching spot.
Farms and Farmers Markets
The oldest and largest open-air market, founded in 1934 by Island farmers, and revived in 1974 by a group of hippies, Yankees, and retired English teachers. The market features a variety of produce, baked goods, prepared food, seafood, chocolate, flowers, herbs, wool. Open seasonally in the summer through October, on Wednesdays and Saturdays.
Successful farm stand that sells a large variety of purchased items as well as their own produce and other goods. They also run a co-op as opposed to a CSA (Community Supported Agriculture), where members can pay up front and then, year-round, select whatever they want from the farm.
Art and Cultural Centers
African-American Heritage Trail of Martha’s Vineyard
A nonprofit organization with over thirty sites, each with descriptive plaques, dedicated to the historic contributions made by people of African descent, each of which helped shaped the Vineyard as we know it today. They offer fully narrated driving and walking tours and workshops. Their mission is to continue to research and publish the previously undocumented history, while involving the community in the identification of the contributions made by people of color to the island.
Vineyard Artisans Festival West
Art gallery, open since 1995, providing a link between the community and the arts, while promoting Island artists and artisans. They offer many shows throughout the year, including on holidays. Visit their website to view their upcoming schedule of shows.
Shops
Oldest retail business on the Vineyard, opened in 1858 and provided locals with basic goods. Today, Alley’s remains an emporium of essentials, and the building itself is part of the Vineyard Preservation Trust. Next to Alley’s General Store is the popular 7A Foods, a local breakfast and lunch favorite and hidden gem, well known for their ‘Liz Lemon’ sandwich, hot homemade pastrami, turkey, Swiss, coleslaw, Russian dressing, and potato chips on rye.
A huge pottery studio, started by Cambridge local, Geoffrey Borr. Geoffrey’s hand-crafted pottery is distinctive of seascapes from mugs to lamps, and so much more. He also designs a triple fire collection, which is a special glaze process that produces bright patterns unique to each piece and sells potter collected during his travels to Asia.
This state-of-the-art glass studio, established in 1992, and located in a quaint barn, has two galleries with rotating work from local artists and Martha’s Vineyard Glasswork designs. In their upstairs gallery, they curate one of a kind sculptural works and offer frequent glassblowing demonstrations in their downstairs viewing space.
An exotic and exquisite handmade jeweler, in business for over thirty-five years. Owner and artist Sioux Eagle, designs and crafts each piece in her West Tisbury home studio, by-appointment-only. She also has a collection of beautiful hand-fabricated work.
The oldest and largest gallery on the Vineyard, family-owned and located in the iconic red barn. They gallery is both indoor and outdoor, in their courtyard, displaying national, regional, and local artists. The Granary Family owns three locations of galleries on the Island, the Granary Gallery and the Field Gallery, both in West Tisbury, and North Water Gallery, in Edgartown.
Field Gallery and Sculpture Garden
Family-owned, outdoor sculpture gallery, across the street from Alley’s General Store, featuring contemporary art by emerging and established artists. The gallery hosts three spaces with rotating exbibits, while outside the field gallery features whimsical sculptures, by Field Gallery founder Tom Maley, and other artists.
Restaurants, Cafes, and Bakeries
A New America restaurant, located in a contemporary and rustic tavern, serving locally harvested, seasonal, and made-from-scratch food for dinner, both indoor and outdoor on their beautiful patio.
EDGARTOWN:
Wildlife Refuges, Sanctuaries, and Conservation Land
One hundred and fifty acres of oak, pine forest, wooded wetlands, salt marsh, and open meadow. A great place to birdwatch, and the largest single gift of land received by the Sheriff’s Meadow Foundation in its history. There are many trails on the property including the Garrett Family Trail, which is a self-guided nature work. South of the Garret Family Trail is purple trail, a little over a mile, designed specifically for mountain bicyclists, with two-hundred feet of elevation change and challenging winding courses.
A three-hundred-and-fifty-acre sanctuary, and home to over a hundred species of birds with over four miles of trails through woodlands, meadows, ponds, and salt marsh. Mass Audubon offers a number of classes, programs, and activities for young explorers and adults by foot and by kayak.
Sightseeing and Architecture
‘Jaws’ Bridge, also known as, the ‘Big Bridge, to locals, originally called the American Legion Memorial Bridge, located in Joseph Sylvia State Park and Beach. The bridge is so well known, because it was the filming location of the shark attack in Steven Spielberg’s Jaws (1975). The bridge is a great place to take a scenic drive as it is in between Sengekontacket Pond and Nantucket Sound and connects Oak Bluffs to Edgartown.
The island’s oldest surviving residence, built in 1672, and continuously owned by the Vincent family until 1940. It was constructed using traditional techniques of medieval England and once stood on twenty acres of farmland. The hours was donated to the Vineyard Preservation Trust in 1977 and moved to the Dr. Daniel Fisher House property for use as a museum.
The Vineyard Gazette Building (Not Open to Public – Rumored Haunted)
This pre-Revolutionary War landmark, was originally a residence, it was acquired by Henry Beetle Hough, publisher of the Vineyard Gazette in 1938, and has been used as a newsroom and printing operation since. The Gazette building is also rumored to be haunted, and they offer building tours year-round.
Beaches
Popular, public sandy barrier beach with surf on one side and calm waters on the other side, great for swimming and boogie boarding, plus, there is plenty of free public parking.
Stretch of sand and dunes, links Edgartown and Chappaquiddick, owned and preserved by The Trustees of Reservation. This barrier beach is an important nesting habitat for offshore birds. Over sand vehicles (OSV), with the appropriate permits, are allowed to roam on certain parts of the beach.
Activities and Sports
A gorgeous semi-private golf club located on Sengekontacket Pond, considered one of the premiere golfing experiences in the northeast. They also have six Har-Tru tennis courts, a full-service café, open seasonally, and specific areas dedicated to special functions.
This one-hundred and sixty-two acres, is both a working farm and educational hub, managed by The Trustees of Reservations, and farmed by Morning Glory and Grey Barn. One the property, The Trustees have built a teaching kitchen and offer educational programs and events, meanwhile Morning Glory and Grey Barn cows and sheep graze the fields, meanwhile, The Trustees house sheep, goats, chickens, and ducks in the barn. View their Facebook page (@TheFARMInstiture) for programing and events.
Travel
Year-round, two car ferry to the island of Chappaquiddick, which is five-hundred and twenty-seven feet from Edgartown port. Besides kayaks, or your own boat, this is the only way to access Chappaquiddick as there is no bridge connecting the island to the Martha’s Vineyard mainland. You can pay for the tickets via a deckhand, who will collect fares (cash only) and tickets, or there is an automatic teller machine near the port, where you can pay via debit or with credit card. The line to board the ferry can get very long during the peak summer months, it is best to plan ahead and get to Chappaquiddick early in the morning to avoid the lengthy lines.
Lighthouses
Open to visitors, view the Martha’s Vineyard Museum website for the seasonal schedule. This lighthouse marks the entrance to Edgartown Harbor and Katama Bay. The light was constructed in 1828 when Congress approved the building of a pier and a light house at the entrance to Edgartown Harbor. The first light house constructed included a two-story dwelling. After the Great Hurricane of 1938, which caused significant damage, the United States Coast Guard tore down the building, and replaced the lighthouse with a cast-iron light, originally located on Crane’s Beach in Ipswich, Massachusetts, that was dismantled and relocated to Edgartown Harbor. The light remains an active aid for navigation today and sits on sandy dunes, opposite the iconic Harbor View Hotel. It is about a five-to-ten-minute walk, depending on your pace from the street through to the light, and on a clear night, it is a wonderful place to view the starry sky.
Farms and Farmers Markets
A farm stand, bakery, and market, founded in 1975, and open year-round. The farm grow about sixty-five acres of vegetables and small fruits, and a have a small pasture, located in Chilmark, which they keep beef cows and harvest forty-five acres of hay. They also own a flower farm, located in West Tisbury. On location at their farm stand, in Edgartown, they produce made-from-scratch baked goods, along with soups, salads, and sandwiches, and they stock groceries.
Shops
The ultimate old-fashioned bookstore experience on Main Street in Edgartown! An independent bookstore with bestsellers, art, cooking, education, gardening, history, music, nature, pets, psychology, poetry, travel, young adult, and so many more book genres.
A newly founded, year-round, charming boutique, a former bait and tackle shop, Captain Porky’s, offering a curated collection of apparel and home goods. They, not only, sell in-store, but you can also purchase online.
A trendy and high-end luxury boutique, in business since 1969, selling clothing, shoes, accessories and home goods.
Martha’s Vineyard Beach Boutique
Gift and souvenir shop selling unique nautical gifts and a ton of beach supplies, including chairs, umbrellas, swimsuits, beach games, goggles, towels, coolers, sunscreen, sunglasses, hats, and so much more. They also have an exclusive product line.
Lifestyle and travel inspired shop selling a mix of curated home and personal accessories, gifts, and ocean and sun inspired essentials. You can shop their unique collection both in-store and online.
Blackwater Trading Co.
Seasonal lifestyle and outdoor shop selling YETI gear, clothing and hats, home accessories, and various souvenirs.
Locally owned boutique selling carefully curated clothing, from statement pieces to casual wear.
A colorful boutique selling printed resort-wear clothing and accessories for women. Lilly Pultzer started around 1959 when Lilly Pulitzer, a socialite, whose husband owned several Florida citrus groves, opened her own juice stand in Palm Beach, squeezing oranges, lemons, limes, and pink grapefruit, which made a mess of her clothes. Lilly asked her dressmaker to design a dress that would camouflage the stains. Her customers loved her juice-camouflaging dresses so much, that she started selling more shift dresses than juice. She quickly became a fashion sensation and a creator of American resort wear, as we know it today.
Found in 1977, selling casual and classic American sportswear for both men and women. They are known for their attention to detail, selling quality silks, cottons, and cashmeres, alongside embroidered and hybrid prints, designed by their in-house team. Today they have over one-hundred and forty retail stores in the United States.
An iconic Michigan favorite and specialty fudge shop, with a variety of flavors. They have four locations in Martha’s Vineyard, including two in Edgartown, café, and fudge shop, plus locations in Oak Bluffs and Vineyard Haven.
British clothing and accessories brand started in 1988, and inspired by the ski slopes, they first started selling outdoor clothing at resorts, and named their brand ‘Fat Face’ after the ski run in Val d’Isère, La Face. Today they have well over two-hundred retail locations.
An apparel store selling a wide variety of Martha’s Vineyard branded apparel such as hoodies, sweatpants, T-shirts, sweaters, and more.
A seasonal, costal style apparel store, opened in 1994, selling men and women’s clothing, accessories, and shoes.
A popular and charming bookstore inspired by the Portobello flea market in London, England, with an eclectic selection of books, art, souvenirs, and trinkets.
A bargain warehouse style department store selling fishing and beach geal, apparel and work boots, watches, knives, cameras, sunglasses, household items, and golfing, camping, and paintball equipment.
Breweries
An American microbrewery, one of the few breweries, located in the Vineyard. They have two locations, one in Edgartown, Martha’s Vineyard, and the other in East Falmouth, Cape Cod. Their location in Martha’s Vineyard, is a brewery and tasting room, located in a quaint farm with indoor and outdoor seating amongst their beautiful gardens. They have a seven-barrel brewing system, which allows them to rotate up to ten different beer styles. They also have to-go 32 oz. crowlers and 64 oz. growlers, plus on-site snacks, food, and merchandise.
Restaurants, Cafes, and Bakeries
Both a bakery and café. Their café is located in Vineyard Haven, while their bakery is located in Edgartown. The bakery offers baked goods, pastries, desserts, and coffee, baked fresh daily. Their café is open year-round for breakfast, lunch, and dinner, serving soups, salads, sandwiches, entrees, and more. Both baker and cafe have both gluten free and vegetarian options.
Off main street, this café serving breakfast and lunch is popularly known for their coffee and sandwiches. They also sell baked goods, some of which are vegan friendly and savory breakfast entrees. This place can get very crowded in the summer.
Dine like a local! A small and quaint diner-style coffee house serving breakfast and lunch specials, across the street from Edgartown Harbor.
Family owned and operated for over forty years, serving seasonal comfort food for breakfast, lunch, and dinner, with a beautiful and relaxing outdoor patio with a small garden.
All American cuisine in a retro-style diner, serving up classic and hearty dishes for breakfast and lunch with classic drinks, such as root beer floats, milkshakes, and various flavored soda.
A popular and highly rated seasonal and lively seafood-focused restaurant with a raw bar, an extensive cocktail menu, and occasional live music. They are located conveniently on Main Street in downtown historic Edgartown.
Charming and elegant American bistro located on Main Street, in historic downtown Edgartown, open for over twenty years, serving dinner using local ingredients, inspired by the culinary styles of Italy, France, and Spain. They have a seasonally evolving menu and an extensive wine list. This place is very popular, especially during the summer, reservations are highly recommended.
A cozy, modern and seasonal kitchen, and bar, started in 2005 by husband-and-wife team, who work with local farmers and fisherman, to source local ingredients, and frequently change their menu to feature American fare with European influences. They have a beautiful outdoor garden patio, and inside dining, which can get very crowded, reservations are highly recommended.
An extremely popular, seasonal, local and tourist favorite with harbor views, open for over fifty years, serving lunch and dinner and drinks. They have a great outdoor deck with a bar and extensive ocean views, including the Chappaquiddick harbor.
Chef-owned and operated seasonal, modern, and romantic, restaurant and bar, open for dinner, and located in a restored whaling captain’s house. They source local seafood and native ingredients, from community farms, for their French inspired, seasonally rotating menu. Feast in their elegant dining room or outdoors in their tented patio.
Lucy Hank’s Restaurant and Café
Located in a renovated house, opened in fall 2012, serving casual, homemade breakfast, lunch, and dinner and drinks, seasonally, using fresh and local ingredients. Plus, they source humane certified meats and try to find ecofriendly solutions to minimize their use of plastic.
Atria Restaurant and Brick Cellar Bar
A fine dining restaurant and a swanky ‘brick cellar’ bar, serving new American global comfort food, with a seasonally rotating menu, sourcing food from local farms and fisherman. Their wine menu is quite extensive, six pages!
The Terrace at the Charlotte Inn
An experience in and of itself, The Terrace within the Charlotte Inn is an elegant and romantic bistro serving farm-to-table steak and seafood dishes in an outdoor garden-like eclectic atmosphere.
A seasonal, popular Italian American style bistro, with gluten free options, serving dinner in their dining room and at their bar. With a wonderful wrap-around bar outside, Chesca’s is located on the main floor of the Vineyard Square Hotel & Suites.
A contemporary bistro, in an intimated setting, known for serving fresh seafood classics for lunch and dinner, favored by locals and tourists. They have a unique menu with craft beer, cocktails, and they serve the largest oyster selection on the vineyard! Dine inside or outside on their beautiful patio, which is lit up at night.
A highly revered, seasonal, casual, and upscale renovated restaurant, open for dinner, with two full bars, serving wood-fired pizzas and American cuisine.
A seasonal, multi-level, elegant seafood, and steak restaurant with indoor and outdoor seating, open for lunch and dinner. They serve fresh and wild caught seafood, as well as, USDA certified steaks, including Japanese A5 Kobe Steaks that perfectly compliment their extensive wine list.
Literally located behind a bookstore! A charming, hidden gem behind Edgartown Books on Main Street, serving breakfast, lunch, dinner, and drinks, including coffee and tea, on their beautiful patio. A perfect place to meet up with family and friends, catch a drink after work, or cozy up with a book and a great meal.
Homemade ice cream and low-fat yogurt right on the Vineyard, scooping for tourists and locals for over fifty years, with locations in, not only Edgartown, but also Oak Bluffs and Vineyard Haven. They have a nice selection of unique flavors, a great place to stop in for a mid-summer treat to beat the heat.
CHAPPAQUIDDICK:
Wildlife Refuges, Sanctuaries, and Conservation Land
Stunning, scenic wildlife refuge barrier beach, with an expansive salt marsh and pond, spanning five-hundred and sixteen acres on the eastern edge of Chappaquiddick Island. The refuge is owned and managed by The Trustees of Reservations, it extends from Wasque Point, past Cape Poge Lighthouse, all the way out to The Gut. The refuge is home to the century-old Cedars, which are low-growing red cedar trees, artfully sculpted by nature. Explore this vast refuge on foot, or by purchasing a permit for an over sand vehicle (OSV) adventure.
Pronounced (way-skwee), this two-hundred acre shifting sandbar and windy, eroding beach at the southern end of Chappaquiddick, was once a great white sand beach with boardwalks. Between the storms, fires, and rapid currents, this protected reserve has never been quite the same. Even though the refuge is not an ideal place to swim, it is a perfect place to take a stroll, have a picnic or, if you are an avid fisher, this is a popular location for surfcasting. Owned and operated by The Trustees of Reservations, they allow over sand vehicle (OSV) explorations, with appropriate permits.
Sightseeing and Architecture
A hidden and secluded Japanese-style garden framed around a short winding trail, with native and exotic plants and flora, a small pond, with turtles, frogs, and goldfish, and an azumaya, a traditional arbor-like shelter. Mytoi dates back to 1954, when architect Hugh Jones received a three-acre parcel of land, as payment for the designing the summer home of Mary Wakeman. Jones developed a love for Japanese gardens during his military service and spent so much time planning and crafting his garden paradise and referred to it has his toy, hence naming the garden ‘my toy’ which he spelled as Mytoi. After Jones died, the land went back into the hands of Wakeman, who sold the property to The Trustees of Reservations. Even though the gardens may be easy to miss, they are well worth the visit. Parking for Mytoi is extremely limited, located right before the air pump station, which is before you reach Dyke Bridge.
Cape Poge Elbow and The Gut
Known as ‘the elbow’ this mile and a half, narrow, stretch of barrier beach extends from Cape Poge Lighthouse all the way to The Gut. The elbow’s widest point is roughly two-hundred and fifty feet across. The Gut an area of high current, pushing water from Nantucket Sound into Cape Poge Pay, an another highly attractive fishing area. On the other side of The Gut, is North Neck. North Neck is a peninsula that extends roughly two-thousand feet into Cape Poge Bay, a popular fishing and bird watching spot, and reservation of the Chappaquiddick Wampanoag Tribe.
Dyke Bridge
Short bride connecting Dike Road on the mainland of Chappaquiddick to East Beach on Cape Poge Wildlife Refuge. The bridge is well-known because of a tragic incident and scandal involving Massachusetts Senator Ted Kennedy, who was involved in a car accident on July 18th, 1969. The former senator, supposedly, took a wrong turn that resulted in his car flipping over, off the bridge. This incident took the life of Mary Jo Kopechne, a former campaign aid to his brother Robert Kennedy, who ended up drowning. Kennedy fled the scene and didn’t report the accident until the next day. Recently, a plaque was placed on the bridge in remembrance of Mary Jo Kopechne. Regrettably, residence feel like the incident defines Chappaquiddick, as the bridge has become an oddity of sorts, a twisted tourist destination. Many know very little else about the island of Chappaquiddick and its roots, which involves the Chappaquiddick Wampanoag Tribe, who continue to reside on their homelands of Chappaquiddick and Martha’s Vineyard.
Beaches
Also known as Leland Beach, a scenic hundred acre barrier beach on Cape Poge Wildlife Refuge, overlooking Nantucket Sound, owned and maintained by The Trustees of Reservations. A great place for fishing, swimming, birdwatching, walking, and picnicking.
Activities and Sports
Royal and Ancient Chappaquiddick Links
A beautiful nine-hole golf course, over a century old, founded by Frank Marshall, who got the idea after hiking on a Scottish and Irish linksland, on a backpacking trip in Europe. A linksland is a sandy wind-sculpted costal terrain, often used as the sight of golf courses. The course has sweeping views of The Neck and Nantucket Sound.
CHILMARK:
Wildlife Refuges, Sanctuaries, and Conservation Land
A protected nature reserved, formed by thousands of years of glacier expansion, and owned by The Trustees of Reservations. The rocky shoreline, overlooking Vineyard Sound, is comprised of wetlands, woodlands, coastal plains, and hilltops, including the three-hundred- and eight-feet Prospect Hill, the second highest point in the Vineyard, renowned as a World War II military outlook and garrison. Other scenic points, include Menemsha Hills Reservation Beach, accessible by the Brickyard Trail, roughly three miles, through woodlands to the beach. Also, worth the hike is the Beach Trail, which you can get to off the Brickyard Trail, that brings you directly onto the beach and has a few gorgeous overlooks.
Also known as the islands summit, Peaked Hill is the highest point on Martha’s Vineyard, at three-hundred and eleven feet. In fact, Peaked Hill is not only the highest point on the Vineyard, but also, the highest point above sea level on Cape Cod and Nantucket. The hill is owned by the Martha’s Vineyard Land Bank. The top of the hill boasts stunning views of the Vineyard Sound, Menemsha Bight and Aquinnah.
Beaches
Known as the ‘surfers’ beach’, and for its scenic views of the clay cliffs. There is a section of the beach that allows nude sunbathing and swimming, this is the only beach on the Vineyard that allows nudity. The beach is typically, residence only and you need a beach pass/vehicle sticker, seasonally, to access the beach. During off-season, you do not need a pass. View the Town of Chilmark’s Beach Information webpage for more information.
Great Rock Bight Beach and Preserve
Twenty-eight acres, comprised of grassy fields, wetlands, seaside bluffs, sandy coves, and ponds, all owned of the Martha’s Vineyard Land Bank. The ponds host a rare population of clam shrimp, the only place they have been documented on the island. Furthermore, Marl Pond, was used to preserve the baskets of hemp ropes of early settlers due to its natural acidity.
Farms and Farmers Markets
Started as a large vegetable garden selling at the side of the road, the farm stand expanded the roadside stand and added fauna and flora. They sell a variety of cheeses, including feta, raw milk, yogurt, seasonal produce, beef, lamb, and baked goods.
A renowned certified organic farm, award winning creamery, farm stand, and bakery. Next to the modern-minimal farm stand, selling a variety of cheeses, produce, baked goods, and souvenirs, you can see their adorable calves, raised on site, they also have chickens and pigs.
One of the Vineyard’s oldest farms, established in 1762, with over one hundred acres of farmland, specializing in sheep and wool. On site, they have a farm shop selling eggs, meat and poultry, woolens and clothing, and other specialty products, such as jam, cocktail spreads, salts, vinegars, and more.
Shops
A fun and lively art gallery, created by artist Abraham Pieciak and painter Brandon Newton in 2019, with a vision that the gallery would be place that people can gather and celebrate art. In addition to their own work, which include paintings and three-dimensional art, they also carry the work of several other artists whose pieces include glass, pottery, woodwork, copperwork, and more.
An art gallery, in business for fifteen years, displaying and selling pieces crafted from copper, including weathervanes, lighting, jewelry, paintings, and wall art, each crafted by hand, using soft and sharp tools.
Old-fashioned, seasonal, community market and gathering place, selling everyday basics, produce, products, household goods, and delicious eats for breakfast and lunch.
Restaurants, Cafes, and Bakeries
Family-owned, seasonal, and widely renowned fish market, open since 2004, selling fresh seafood direct from the fishermen to the public at lower prices, making this market truly unique. The market is very small, located in the fishing village of Chilmark, right next to the Menemsha Basin.
A seasonal, and extremely popular fish market, started in 1969, located around the corner from Menemsha Fish Market, selling locally caught seafood for fair prices. Lines to order can get extremely long, but Larsen’s is worth the wait. Take your fresh seafood down to the dock or take a short walk to the Menemsha Public Beach.
A small, charming spot, serving breakfast and lunch, known for their sandwiches and chowder. They have a few picnic tables if you are looking to enjoy your meal or snack outside. A great stop along the way if you are exploring the Menemsha Harbor.
A rustic, lively, upscale, and casual eatery, sourcing local ingredients whenever possible, and encouraging customers to bring their own booze.
AQUINNAH:
Wildlife Refuges, Sanctuaries, and Conservation Land
Epic clay cliffs carved by glaciers, known for its scenic beauty and historic significance to the Wampanoag tribe. Below the cliffs is a breathtaking stretch of sandy and rocky, public beach, Moshup Beach, part of the Aquinnah Headlands Preserve. On top of the cliffs is Gay Head Light, a historic lighthouse and filming location in Jaws (1975). The ancestors of the Wampanoag people lived at Aquinnah, which at the time was known as Gay Head, and throughout the Vineyard, which was known as the island of Noepe. The Aquinnah Wampanoag believed that the giant, named Moshup, created the vineyard and the neighboring islands. Moshup taught the Wampanoag how to fish and catch whales. It is also believed that the Wampanoag would wade into the water to catch whales and fling them against the cliffs to kill and cook them; the blood of the whales stained the cliffs read and the coals from the fires stained them black. Today, the Aquinnah Cliffs, owned and protected by the Aquinnah Wampanoag Tribe is the most photographed place on the Vineyard. The clifftop observation point, atop the cliffs, is a wonderful place to catch sunset. Meanwhile, the public beach down below is a great walk and an even better place to get up close to the cliffs and marvel in awe of their rich history.
Forty nine acre preserve, protected by the Martha’s Vineyard Land Bank Commission, the Sheriff’s Meadow Foundation and the town of Aquinnah, the Headlands Preserve boasts some of the most amazing views on the Vineyard, and has a network of seasonal, and some year-round, trails and an abundance of wildlife. The preserve is divided into the north and south head. The north head, above the cliffs is open seasonally, while the south head, is open year-round, and leads down to the southern part of Moshup beach.
A scenic and quiet place of both cliffs and beach, known for its ‘remote’ feel. Zack’s cliffs is located on the south head area of the Aquinnah Headlands Preserve, Zack’s Cliffs and Beach are located off of the Moshup trail, less than a half of a mile trail, open year-round, and great for walking, hiking, walking, and bird watching.
Rocky coast and beach located on the southernmost point of Aquinnah, while the beach stretches from Aquinnah to Chilmark. Squibnocket Point is accessible by Squibnocket Farm Road and offers gorgeous views of the Atlantic.
Beaches
A two mile, secluded, dune beach with public access. Great for snorkeling, fishing, birdwatching, swimming in the calm Vineyard Sound waters, and walking the sandy shores
Activities and Sports
A surf shop, in business since 2012, offering stand up paddling (SUP) lessons and tours, included guided outings and multi-sport adventures. They also offer stand up paddling yoga sessions.
Lighthouses
The first lighthouse built in the Vineyard, on the cliffs of Aquinnah, also known as Gay Head Cliffs, and one of the first in the United States to receive a Fresnel lens in 1856. Charles W. Vanderhoop, Sr., a member of the Wampanoag Tribe became the first Wampanoag keeper in 1920. Gay Head Light was a used as a filming location for Steven Spielberg’s Jaws (1975). The light has been moved away from the cliffs twice, threatened by the eroding clay. Today, the light is one of the most photographed on the Vineyard and stands picturesque atop the cliff. Tours are offered seasonally, however the grounds are open year-round for visitors.
Arts and Cultural Centers
A non-profit, that aims to preserve, educate, and document the Aquinnah Wampanoag history, culture, and contributions. Open seasonally the Aquinnah Wampanoag Indian Museum is housed in the historic Edwin D. Vanderhoop homestead, which has been restored and listed on the National Register of Historic Places. The museum’s exhibit rooms include the sundeck, which houses the industry section, the historic kitchen, the bedroom, and outside, the patio, with views of the dunes, heath lands, and shores of Moshup Beach.
Shops
A family-owned gift shop, open seasonally, in small Aquinnah town center, located before the Aquinnah Cliffs, selling local Wampum gifts and costal home goods
A seasonal, Wampanoag family-owned business on Aquinnah cliffs, founded in 1974, selling Wampanoag-made jewelry, scrimshaw, t-shirts, apparel, and much more. The owner, Martha Vanderhoop’s father, Charlie Venderhoop, was born at the Gay Head Lighthouse in 1921, and his father was the first and only Wampanoag Principal Keeper.
Restaurants, Cafes, and Bakeries
Native owned, hidden gem, baking breads and pastries from scratch, and producing delicious wood-fired pizzas, and provisions.
Family-owned and operated, shop, and indoor and outdoor restaurant, founded in 1940, by Napoleon B. Madison, a member of the Wampanoag Tribe. Located at the top of Aquinnah Cliffs, the Shop and Restaurant have incredible views of the cliffs and Vineyard Sound.
The Little Blog of Magic 
This was a great area where we visited many times.
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Thanks for the comment! Martha’s Vineyard is a great getaway. Every time I leave on the ferry I am ready to turn back around and stay for longer!
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Yes such a great outing for us.
Anita
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