10 Reasons to Visit Martha's Vineyard in the Winter

Sure, the busiest season on Martha’s Vineyard is the summer, but that’s certainly not the only time to join us on our magical Island. The winter is one of the most beautiful times on the Vineyard. A quick and easy ferry ride of only 45 minutes sets the escapist tone of a wonderful winter getaway. And here are 10 reasons to make the trip! As always, be sure to visit our calendar to see all the events happening; more are added everyday. ​
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1. Holiday Happenings 
There is arguably no place more festive for the holidays than the Island of Martha’s Vineyard. With our quaint towns, all decorated in their own unique ways, and our incredible one-of-a-kind merchants, holiday shopping is simply the best on the Vineyard. And weekend-long events, like those that happen in Oak Bluffs, and Tiz the Season in Tisbury and Christmas in Edgartown, put even the scroogiest of scrooges into the holiday spirit. Santa's Oak Bluffs Open Market offer shoppers an opportunity to purchase unique gifts directly from the makers, enjoy live music and yummy food, and have pictures with Santa — for kids and pets alike! Plus, there’s free horse-drawn hayrides, a puppet parade, and an Old Fashioned Christmas at the Island’s oldest brewery. Enjoy horse-drawn hayrides, live music on Main Street, a free community viewing of The Polar Express at one of the Island’s oldest movie theaters, a Chanukah Celebration at the Hebrew Center, and so much more during Tiz the Season in the quaint town of Tisbury. Watch the lighting of the Edgartown Lighthouse, enjoy the annual Chowder Contest, visit the delightful holiday Teddy Bear Suite, have breakfast with Santa, and so much more during Christmas in Edgartown.
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                                                                                                Photo: Max Bossman
​2. New Year’s Celebrations 
Martha’s Vineyard is the perfect place to bring in the New Year! Whether you prefer a quiet evening in, a year-end fabulous dinner out, or a fabulously lavish party that goes into the wee hours, the Island is where to be. With countless, romantic boutique inns and B&Bs, quietly saying hello to the new year with your significant other is magical on Martha’s Vineyard. Plus, with award-winning restaurants dotted throughout the Island, you’re sure to enjoy a fabulous “last meal” of the year. And if you like an all-out party on New Year’s, the Harbor View Hotel has got you covered with nosh, two dance floors, fireworks, and a midnight champagne toast.
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3. Discounted Prices 
It’s no secret that Martha’s Vineyard has a reputation as an expensive destination. And while there are budget-friendly options in every season, the prices never get better than in winter. Often, you can enjoy the same, high-end accommodations for a fraction of the price. So if you’ve ever wanted to see what the Island is like, but have had concerns about the cost, come on over in the winter! Sure, you can’t sunbathe, but winter walks on the beach are lovely. Trust us.
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4. Winter Walks 
Speaking of winter walks, the Island truly is a gem to discover by foot. With countless miles of walking trails throughout, Martha’s Vineyard practically begs you to go further, walk more, discover her less seen, inner beauty away from the towns and roads. Take a hike on your own, join Polly Hill Arboretum during the winter months to meander their 70-acre public garden to look for seasonal plants of interest, or go bird watching. The majestic snowy owl is often spotted on the Island, and is truly a sight to be seen!
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5. Snowman on the Beach 
Have you ever? If not, you should. There are few things quite as fun as building a snowman where you usually catch a sunburn.
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6. Snowshoeing
Those miles of trails just mentioned? They’re also simply perfect for snowshoeing! This favorite outdoor winter activity is made even more fun if you choose a trail that leads to the beach. There’s something to be said for standing at the shoreline in snowshoes.
 
 
7. Island Art Classes 
Martha’s Vineyard has a robust art scene, and winter is a wonderful time to dive right into the heart of it. The Island is lucky to have an incredibly active and vibrant art center, Featherstone Center for the Arts, which offers hands-on classes in all modalities throughout the winter. This is the perfect season to check into your inner artist and let your creativity flow — no experience needed! 

8. Big Chili Contest 
What would winter be without food? The Island heats up in January with the annual Big Chili Contest. The daylong event has been attracting crowds from off-Island for years, and there’s a reason for that: It’s a super fun party with live music, drinks, and (of course) chili — all done with an Island twist. 

9. Annual 20 Miler & Amity Island Relay 
The Martha’s Vineyard 20 Miler is a “must” race for die-hard runners of various levels. From highly competitive athletes looking for to test their readiness for Boston and other spring marathons, to dedicated recreational runners, this race offers the chance to combine a visit to one of the East Coast’s most beautiful shore communities with a race on a fast, USATF sanctioned course. But this event is fun for the less serious runners, too, as there’s also a partner “Amity Island Relay.” The Island becomes abuzz with visitors and it’s fun to cheer for the racers along the way. 

10. Martha’s Vineyard Film Festival 
 Come for dinner, and stay for the show — all of them. The Martha’s Vineyard Film Festival runs from March 17-20, at the Chilmark Community Center. Enjoy the incredible lineup of movies, with the opportunity to speak with directors, editors, and members of the community. Moviegoers will also enjoy eclectic food, live music, and guided meditation.

SEE YOU ON THE VINEYARD!