things to do in the winter

Martha's Vineyard Winter
Flickr/Mass Travel (CC BY-ND 2.0)

As the saying goes: “Summer people, some are not!” While Martha’s Vineyard is loved by many as a summer destination, we feel that a Martha’s Vineyard’s winter is an underappreciated gem. In the colder months, explore quiet lighthouses tucked into the white snow or walk into your favorite restaurants without a wait. Embrace the chill and discover the hidden delights of a Martha’s Vineyard winter.


Flip Over Fantastic Food Festivals

While there’s plenty of tranquility in the winter, we’ll let you in on an island secret: sometimes the best way to get through the colder months is a good old fashion party. Of course, it doesn’t hurt that our favorite zany, winter festivals also happen to be food themed. Warm up from the February cold by eating mountainous amounts of chili at the Big Chili Contest. Boogie to the mariachi band that performs all day and feel justified in your eat-a-thon by helping to choose the festival winner. If the thought of eating chili all day isn’t enough to give you heart burn, you may just have the stomach for Wingfest at Shaky’s Cantina. Bring wet wipes and an empty stomach because Martha’s Vineyard winter is ready to deliver some seriously good eats.


Sledding Martha's Vineyard Winter
Flickr/N. Friedler (CC BY ND 2.0)

Play in the Snow

Fun in the sun is not just for summer anymore. The island is teeming with outdoor spots that are all the more gorgeous in the snow. Take a stroll on any of the Vineyard’s beaches, and build a snowman by the water . If you remember to pack your skates, you can glide around the peaceful Jernegan Pond, Sheriff’s Pond, or John Butler’s Mud Hole in Edgartown. Our favorite outdoor activity? Embrace Martha’s Vineyard winter’s reputation for blustery weather by going snowkiting. Just grab your skis, a kite, and some good old fashion grit, and you’ll be off sailing.


Eat to Your Heart’s Content

While it’s true that some restaurants are closed during the off-season, many exciting and delectable spots remain open all winter long.  Take a bite out of the modern American delights at State Road, which, coincidentally, happens to be one of our owner’s favorite restaurants.  For a meal with large portions and no pretensions, we recommend the Wharf Pub where you can order one of our favorite cold weather treats on the island, chowder fries (yes, that’s chowder with fries on top). On date night, head to the Alchemy with its fresh seafood and mouth-watering entrees like their half-chicken (not to mention, their hand-crafted cocktails). The only downside? You’re probably going to leave the island a few pounds heavier than when you came.


Martha's Vineyard Film Festival
Photo: MVFF

Join in on the Arts

No matter what time of year it is, art on the island never sleeps. Many of the island’s most vibrant galleries (including the Eisenhauer Gallery in the Square) stay open throughout the winter. Escape the cold winds by taking in some local culture. If your love of art leans more towards learning than appreciation, Featherstone Center for the Arts offers art classes of all types throughout the Martha’s Vineyard winter.


By far, our favorite event of the season (yes, even behind ChiliFest!) is the Martha’s Vineyard Film Festival in March. Sit back and grab your popcorn for a wide selection of films and have the opportunity to speak with their directors and creators. Plus, all moviegoers get food, live music, and guided meditations. With its quiet serenity, Martha’s Vineyard in the winter is the ideal time to get a little artsy.


The Peace and Quiet of a Martha’s Vineyard Winter

As much as we relish the lively hum that rings over the island in the summer months, the off-season is a time of relaxation and secret pleasures. Whether you’re strolling through the streets of Edgartown or off searching for the perfect sledding hill with friends, you’ll feel like you have the island all to yourself. It’s just you, snow, and sea as far as the eye can see. Take a page out of winter’s playbook and settle down for the season in the luxury suites at Vineyard Square.

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