Maybe I am just a New England girl through and through, but there are few things I love more than embracing the change of the season. And while snow is more of a hope than a promise right now, strolling our town centers still feels like walking through a Vineyard wonderland. This month, I spoke with the people who bring our holiday festivities to life, each town and tradition offering its own take on merry-making. And though their celebrations differ, they all share a common thread – light. December may bring our shortest days, but it’s also known as the season of light, and the Island embraces that. From the public Menorah lightings by Vineyard Chabad, to the Oak Bluffs tree lighting, to the Christmas in Edgartown parade, and every celebration in between, the Vineyard shines in its own distinctive ways.
Taylor Stone, who is the Administrator for the Vineyard Haven Business Association as well as the Clerk for the Vineyard Haven Harbor Cultural District, spoke with me about how these two organizations collaborate with the town of Tisbury to put on “Tis’ the Season”. This month of merriment kicks off with the last First Friday of the year on December 5th.
“First Friday has grown into something people can really rely on, and it continues to grow with the support of our incredible VH community and sponsorship from local businesses,” Taylor said. The MV Playhouse will be hosting an artist marketplace in collaboration with MV Made and featuring over 20 local makers in the lobby, as well as live music by Willy Mason in the theater from 5 to 8 pm. This Friday also marks the start of late-night shopping, with many Vineyard Haven storefronts staying open beyond their usual hours each Friday in December, to support shop-local efforts.
If hitting the town after dark feels daunting, save your shopping for Sunday the 7th when 10% of sales from participating VH businesses will go to Island Grown initiative. While Taylor is excited about the Cranberry Shores Chorus Carolers, the horse drawn carriage rides led by Fred Fisher, and the iconic “snow” the town creates, she was delighted to break the news that the New Years Eve celebration formerly known as “First Night” will return to Vineyard Haven for the first time in 25 years – the perfect way to bid farewell to 2025. This revival celebration will be led by the Youth Task Force and held by the Playhouse on the 31st, and more information about it will be published by the VHBA and the Youth Task Force soon. Taylor describes the theme of the Vineyard Haven holiday events as “family friendly and financially accessible”, and she encourages everyone to attend as we continue to watch our port town grow.
By the time you’re reading this, you have probably already enjoyed Light Up Oak Bluffs. Interim Director of the Oak Bluffs Association, Jen Adamson, shared a glimpse into the history of the event and what it takes to make it happen.
“Light Up Oak Bluffs actually grew out of some very simple community traditions: neighbors and local families gathering in Healey Square, shops staying open a little later, and volunteers decorating downtown together. Over the years, those pieces naturally came together into the weekend we know today, with carriage rides, holiday markets, cocoa, music, and more businesses joining in. But the heart of it hasn’t changed. It’s always been about tradition, and local families coming out to make memories together.” Jen continued by describing what happens behind the scenes. “It’s really just a bunch of local folks doing their part. Friends of Oak Bluffs volunteer to make the big red bows for the Healey Square tree. The Highway Department brings in the tree itself, which is arranged by Mahoney’s. Stefanie Wolf runs her Snowflake Scavenger Hunt, placing paper snowflakes in participating shops so kids can get their passports stamped as they explore town.”
This year there is a new tradition starting to take shape: the Oak Bluffs Holiday Stroll on December 11th and 12th from 3 to 7 pm. “Downtown shops will each be hosting an artisan pop-up, and it’s a really fun way to discover local makers. We’ve got businesses like OSO, Toteally Yours, Craftworks, Curio, Sanctuary, Stefanie Wolf Designs, Lazy Frog, Jubilee, SEABAGS, and Basics all participating, along with a great lineup of island artisans” said Jen. “It already feels like something that’s going to become a favorite OB holiday tradition.”
The Chabad on Martha’s Vineyard will host a series of Island-wide gatherings throughout December, not only for those who observe Hanukkah, but for anyone interested in coming together to enjoy Jewish culture. Co-Director Rabbi Tzvi Alperowitz shared with me some of what’s planned. The festivities begin on December 7th with a menorah-making workshop for local kids and families. Then to officially welcome Hanukkah on December 14th, the Chabad has partnered with the Edgartown Board of Trade for a community gathering in the Edgartown Mini Park at 4 pm. “There will be a large menorah lighting, a live band playing Hanukkah music, a break-dancing show, latkes, donuts, children’s crafts, and entertainment. Basically, a big, fun party for all,” Tzvi said.
Additional public menorah lightings and celebrations will follow in Ocean Park in Oak Bluffs, and in Owen Park in Vineyard Haven, with more details to come from the Chabad. For those who prefer to join from home, the Chabad will also offer a community Zoom event titled Eight Voices for Eight Nights, where eight community members will each speak for five minutes about the holiday.
“One of the most beautiful things about Hanukkah is the tradition of bringing light into darkness,” Tzvi shared. “It’s about giving that light to someone who might need it. Each night we light a candle and celebrate, and everyone is welcome to take part.”
He also spoke about the significance of coming together during these polarizing times, and how meaningful it is to embrace our differences. “A menorah is only a menorah because it has eight different branches, each offering its own purpose,” he said.
More information about local Hanukkah events will be posted on the Chabad website in the coming days, and Tzvi encourages everyone in the community to join in the celebration.
Christmas in Edgartown will celebrate its 44th year beginning December 11, and Edgartown Board of Trade Director Erin Ready shared with me why it remains one of the Island’s most enduring holiday traditions. “Many people don’t realize that Christmas in Edgartown began as a small, grassroots shopping weekend created by local business owners during the quiet winter season,” Erin explained. “Merchants decorated their storefronts, hosted open houses, and encouraged neighbors to come downtown to fill a few inn rooms and support holiday shopping.”
Over the years, the weekend has grown significantly, and yet it still carries the same community-driven spirit. “Many of those early organizers are still here and continue to lead by example,” she said. “Today, dozens of businesses and nonprofits participate, and the weekend spans a full calendar of activities while maintaining its small-town charm. At its core, the mission remains the same: business owners, volunteers, and community groups coming together to create heartwarming holiday programming for residents and visitors.”
The full schedule of events is available on the Christmas in Edgartown website, featuring everything from the Boys & Girls Club Teddy Bear Suite and the Sweet Homes of Edgartown Gingerbread House Contest, to live music at the Wharf, the Most Festive ’Fit Contest on the Village Green, the iconic Donaroma’s Light Show, the Edgartown Christmas Parade, and much more.
“It truly takes a village,” Erin said, reflecting on how the weekend comes to life each year. “Every part of the community contributes in some way. We encourage businesses to host events that work for their staffing and operations, and many choose to partner with a charitable cause. Town departments including Police, Fire, the Christmas Decorating Committee, Highway, Parks, and others, each play a huge role in creating the holiday atmosphere that carries through the entire month of December.” Together with the volunteer planning committee, their efforts transform Edgartown into a picturesque holiday haven, reminding us why this beloved tradition has endured for more than four decades.
Winter on an island in the middle of the ocean can feel cold and dark at times, but these holiday celebrations offer so much light. It’s also pretty amazing how most of them come together through volunteer work and community support, and many with the sole purpose of celebration and cultural experience. In a world where consumerism has just about swallowed the holidays, the Vineyard finds ways to preserve the true value in this time of year. Because here, it is less about what we buy, and more about what we share.
For more information about our upcoming winter celebrations, keep an eye out for Holiday Happenings, a section of the Martha’s Vineyard Times publishing on December 11th and featuring a comprehensive guide to the season.
