The big holiday weekends in our towns may have passed, but there’s still so much holiday magic to enjoy on Martha’s Vineyard. With a full weekend and almost a week ahead before the big day, the Island is brimming with festive fun for all ages.
From shopping festive downtown shopping to winter markets and arts and crafts shows to horse-drawn carriage rides and more, there are plenty of ways to soak up the season, support local makers, and make special holiday memories. The magic isn’t over yet—there’s still so much to explore and enjoy across the Vineyard.
Holiday Bazaar at the PA Club & Mo's Lunch
Want the whole shopping experience? After work, stop by the PA Club for dinner at Mo's, live music, cocktails, and shop local gifts from some of your favorite vendors like Gilly B, Relove Decor, Sara Barrington Jewelry, Gwen Nicohols Designs Wampum, Tara Reynolds Art, and more. Grab your friends and make a night out of it!
Where: The PA Club, Oak Bluffs
When: Wednesday, December 17th & Thursday, December 18th, 3pm - 8pm
Holiday Shopping on Martha's Vineyard
What’s so great about shopping small and local on the Island for the holidays? Everything!
When you shop at Martha’s Vineyard businesses, your dollars directly support local entrepreneurs and have a lasting impact on the community. Plus, you’re giving unique, meaningful gifts that hold special significance—both to the shop owners and to the recipients. From hand-crafted goods to one-of-a-kind finds, to festive farm stands, there’s something for everyone on the Island. This holiday season, shop local in Island towns, spread joy, and make your gifts even more memorable.
Winter Farmers Market in West Tisbury
Come enjoy your favorite West Tisbury Farmers Market inside the Ag Hall at Christmas time. There will be some of your most favorite vendors like Enchanted Chocolates (a lot of people like chocolate, especially small batch chocolate), live music, a raffle, a festive feel and more. This market has a special holiday glow to it this time of year. It has quite the different feel from the summer and fall events.
Where: The Ag Hall, West Tisbury
When: Saturday, December 20th, 10am - 1pm
Annual Holiday Chilmark Flea Market
Stop by the Annual Chilmark Church Holiday Flea market at the Chilmark Community Center. Get into the holiday spirit and shop for unique gifts that are sure to delight those on your list from Island vendors. There will be the church table of holiday greens and centerpieces to help you make your home more festive and of course lunch, baked goods and coffee will be available for purchase.
Where: Chilmark Community Center, Chilmark
When: Saturday, December 20th, 10am - 3pm
Vineyard Artisans Holiday Festival
Don’t miss this very special holiday fair, the last of the year for the Vineyard Artisans. It’s the perfect chance to find one-of-a-kind gifts for that special someone who appreciates the charm of an authentic Island-made treasure. From unique hand-crafted items to beautiful holiday gifts, everything at this fair is made with love, one piece at a time. Come support local artisans and finish your holiday shopping in style in downtown Edgartown. The Newes, Rockfish, The Wharf, and Town MV are all open for lunch and dinner if you need a bite to eat.
Where: Daniel Fisher House, Edgartown
When: Saturday, December 20th & Sunday, December 21st, 10am - 4pm
Winter Wonderland in Vineyard Haven
Tis' the Season fun continues! Shopping on Main Street in Vineyard Haven is extra special on Sunday, December 21st. Get last minute gifts, don't forget about maybe something special for you. There will be horse drawn carriage rides in town and the sweet sounds of the Cranberry Shores Chorus caroling through town. Don't forget to grab a hot cocoa or coffee from Nat's Nook, Mocha Motts or Waterside Market to help keep you warm.
Where: Main Street Vineyard Haven
When: Sunday, December 21st, 12pm - 2pm
Additional Holiday Markets on Martha's Vineyard
Island Made Holiday Shop
Enjoy a curated collection of local artists from all around the Island in one place daily through Christmas Eve. The greenhouse at Gayle Gardens will dazzle and delight you with unique finds.
Where: Gayle Gardens, West Tisbury
When: Daily through Wednesday, December 24th, 10am - 4:30pm
World Market Holiday Shop
Step into a winter wonderland at the World Market Holiday Pop-Up Shop. This special holiday shop features handcrafted treasures from around the world, including items from Africa, Haiti, India, Nepal, Guatemala, and Peru. Every item is thoughtfully made, with a strong focus on fair trade practices that directly support the artisans who create them.
Where: Capawock Theatre, Vineyard Haven
When: Daily through Wednesday, December 24th, 10am - 6pm
Misty Meadows Holiday Pony Rides
Take in the winter wonderland and experience the magic of the season with a fun pony ride. The holiday spirit is still in the air, making this the perfect way to create lasting memories with loved ones! Schedule your ride today, click here.
Where: Misty Meadows, West Tisbury
When: Saturday, December 27th, 10am - 12pm
Donaroma's Holiday Light Show
Drive through Donaroma's Nursery and enjoy a magical display of twinkling colors and joyful sounds that capture the spirit of the season. It’s a fun and cozy way to celebrate the holidays for all ages! Tune into channel 87.9 on your radio to add the holiday music to your experience.
Where: Donaroma's Nursery, Edgartown
When: Daily through January 4th 2026, 5pm - 10pm
Ring in New Year's Eve at The Ritz
Kick off the night with Johnny Hoy and the Bluefish live at 8:00 PM, followed by Dock Street Fight Club at 10:30 PM! They'll be rocking out until 1:00 AM, so come say goodbye to the old year and ring in 2026 in true dive bar style.
Where: The Ritz, Oak Bluffs
When: Wednesday, December 31st, 8pm - 1am
Additional Things to Do Over the Holidays
Festive Lights Around Martha's Vineyard
One of the simplest joys of the season is driving through the different towns and taking in the beautiful holiday lights. From Edgartown to Oak Bluffs to Vineyard Haven, to Up-Island, each town has its own unique charm with lights decorating homes, trees, and public spaces. It’s a perfect way to spend an evening with family or friends, enjoying the winter beauty of the Island. Featured at the top of the post are the Elephants at the Harbor View Hotel dressed for the holidays.
Martha's Vineyard Public Libraries
The Martha’s Vineyard libraries are a hub of activity this time of year! They offer programming for all ages, from cozy story times for the little ones to craft workshops and book clubs for adults. Whether you're looking to get in the holiday spirit with some festive reading or explore something new, the libraries provide a warm, welcoming place for all. Visit your favorite library's website for a complete list of programming over the holidays.
Enjoy the Island's Trails
Yes, it’s cold, but it’s also the perfect time to bundle up and explore the Island's scenic nature trails. Whether you’re walking through the peaceful woods or taking in the breathtaking coastal views, there’s no better way to experience the quiet beauty of Martha’s Vineyard during the winter months. So grab your hat, scarf, and boots, and get outside for a winter stroll. Stop in for a cozy lunch at Offshore Ale or the Black Dog Tavern after to make a day out of it.
Martha’s Vineyard has so much to offer this time of year—whether you’re shopping local, taking in festive events, or simply soaking in the holiday atmosphere. Happy Holidays from the Point B family to yours. We hope whatever way you choose to celebrate this season, it brings you joy, warmth, and wonderful memories. We're looking forward to a wonderful 2026!
Thanks for reading On Point MV, a blog about Island happenings. If we missed an event or there's a topic you'd like us to write about, email guinevere@pointbrealty.com