A week ago my husband and I found ourselves blissfully shipping out to Martha’s Vineyard. Cruising the Atlantic from Wood’s Hole to Vineyard Haven, leaving the Massachusetts mainland and all of our commitments and woes behind.

Wind-wiped and holding steady on the bow of My Island Home, last week’s snowflakes were swiftly replaced by salt and sand as my husband and I stepped off the ferry onto Vineyard Haven. It was November and yet, summer was in the air. Martha’s Vineyard was tranquil, desolate, windy, colorful, serene, and absolutely refreshing. It was the perfect off-season on the Vineyard to do either much of nothing or a lot of something.

Off-season is always quieter on the island than the spring and summer months. Many shops and restaurants are closed until next spring, and a few shut their doors earlier than usual, due to the pandemic. Still, there were plenty of intriguing small businesses in Vineyard Haven, Oak Bluffs, and Edgartown, carrying local hand-crafted jewelry, wood, metal, glass work, and other goods. Plus, a handful of delectable restaurants are open all-year. The vineyard is the perfect place to support small businesses and artisans.

My husband and I stayed at a stylish, victorian boutique hotel in the center of Edgartown, called The Christopher, one of the three Lark Hotels on the island. Our stay was wonderful, the customer service was impeccable, and everything was perfectly clean and well-kept. The Christopher’s best kept secrets are: after 4 p.m. every night they put cookie treats out on the concierge desk, and they have a private courtyard with plenty of seats, a mini fridge, and a roaring fire that lights at 4 p.m. and goes until 10 p.m.

Upon our arrival, my husband and I decided to take part in The Christopher’s November special Fall n’ Fun package, offered to guests staying two or three nights. The special includes free vouchers to local vendors including: a Grey Barn Farm cheese tasting upon arrival, a tasting flight at Bad Martha Farmer’s Brewery, a picnic-lunch grab and go bag for two from Morning Glory Farm, two cups of chowder at 19 Raw Oyster Bar, two handcrafted beverage coasters from Chilmark Pottery, and (optional) a Jeep rental for your entire stay. If that wasn’t enough to make our arrival memorable, we were greeted by a bottle of bubbly in our room right by our balcony, with a view of the Edgartown and the ocean.

After we got settled in our hotel, that afternoon after we walked through Edgartown exploring the local shops, looking at restaurant menus, and searching for breathtaking scenic views. We stumbled upon Edgartown lighthouse at dusk and wandered along the beach searching for seashells and planning our next-day trip to Chappaquiddick Island. Edgartown lighthouse is simply stunning and very picturesque day or night.

That night, we had dinner at The Terrace, a fine-dining restaurant located inside the Charlotte Inn. The food, like the atmosphere, was superb. We felt like we had stepped back in time with all the eclectic trinkets placed on the walls and on display in their many rooms. A wonderful place to wander around after dinner and get lost analyzing the wooden crafts and interesting artwork.

We took an early ferry the next morning to Chappaquiddick. In the off-season, the ferry runs on a slightly different schedule than the summer months. Nevertheless, super convenient, quick, and very inexpensive, the barge holds three cars max and takes about five minutes to cross five hundred and twenty-seven feet of ocean from Edgartown to Chappaquiddick Island.

Chappaquiddick is a wonderful escape with miles of serene beaches, hiking trails, and houses hidden all over the island. My husband and I drove all around, stopping at the ever-changing shoreline to take in the waves of the beach and the spider web-looking trees at Wasque Reservation Point. Down the road, near Dyke Bridge, we relaxed and day-dreamt at the exotic Japanese garden, Mytoi. Both Mytoi and the Wasque Reservation were totally deserted, it was like we were on out own private island the whole time.

That very night, as part of The Christopher’s Fall n’ Fun special, we dined on savory chowder and ordered one to many small plates at 19 Raw Oyster Bar, back in Edgartown. A cozy little restaurant with both heated indoor and outdoor seating. We went to bed exhausted from our adventure on Chappaquiddick and pleasantly stuffed.

We woke up the next morning indulging in mimosas on our balcony, devising our day visiting and supporting local businesses. Our first priority was picking up our picnic-lunch for two at Morning Glory Farm in Edgartown, to feast upon at Aquinnah Cliffs Overlook on the western coast, which was about a forty minute drive out. The picnic lunch included a bag of chips, dip, two salads, and two cookies, yet another perk of The Christopher’s Fall n’ Fun package.

On our way to Aquinnah Cliffs, we made a plethora of stops, first at Island Alpaca Company. An alpaca breeder, seller, and educator, with over nineteen acres of land in Vineyard Haven, and home to fifty Huacaya alpaca. The amount of alpacas they care for is quite remarkable. Plus, many of the alpacas are not afraid, and have no problem wandering curiously close to their wooden fence boundary.

Our second stop was at Bad Martha Farmer’s Brewery in Edgartown, to taste a free beer flight thanks, yet again, to The Christopher’s Fall n’ Fun special. Bad Martha got its name based on the legend of Bad Martha. Legend has it, that a mermaid with jet black hair and a devilish grin beckoned a ship’s captain to a patch of lush grapes on the island to brew wine. These grapes became the secret ingredient for brewing a robust and refreshing beer and the mermaid was never seen again. Bad Martha’s is one of the few local breweries on the island, the other is Offshore Ale Company in Oak Bluffs.

Down the road a few miles in West Tisbury, was Chilmark Pottery, the shop of local ceramist and artist, Geoffrey Borr. At Chilmark Pottery we picked exquisitely colorful, and hand crafted coasters, that reminded us very much of the ocean. Additionally, they were totally free, thanks to The Christopher’s Fall n’ Fun special. Both inside and outside the pottery shop there are shelves upon on shelves of locally crafted clay goods on display to gaze at and admire.

Less than a mile down the road, in West Tisbury, was Martha’s Vineyard Glassworks, a small shop where artists and craftspeople can explore and educate themselves on the beauty of glass making. Starting in the fall they carve exceptional blown glass pumpkins of various sizes and hues. Upstairs, there was a small exhibit of pricier glass pieces on display. Every single piece was intricately delicate and very impressive.

After a short drive, we stopped at the oldest operating retailer on the island, in business since 1858 and located in West Tisbury, Alley’s General Store. Across the street was a wonderful outdoor sculpture gallery and next door, in Chilmark, was Grey Barn Farm. We made a quick stop at the farm to shop the farm-stand, awe over the baby cows, and see exactly where our cheese-tasting upon arrival, a part of The Christopher’s Fall n’ Fun special, derived from.

It was almost dusk and we were not far from the Aquinnah Cliffs, but we had to stop at the renowned Larsen’s Fish Market. A hole-in-the-wall takeout window by the docks in Menemsha, praised for their fresh seafood and chowder. We devoured two lobster rolls, one cold and one hot. They were both so delicious it became extremely difficult to decide which one we enjoyed more.

Less than twenty-minutes later, we were at the colorful clay Cliffs of Aquinnah gazing at Gay Head Lighthouse, one of the most photographed overlooks on the island, and the best place to watch sunset. Legend has it, the Aquinnah Wampanoag Tribe 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 red and the coals from the fires stained them black. The beach down below the cliffs is a wonderful place to stroll and take in colorful cliffs up close, and watch sunset from a slightly different angle than the overlook viewing platform.

Dinner in back in Edgartown at Alchemy Bistro and Bar was nothing less of incredible and quite romantic. My husband and I toasted to our wonderful time on Martha’s Vineyard, dreading our journey back to the mainland, and plotting our next trip at the exact same time…

Cheers!