Late November through mid-December is one of my favorite windows for a Martha’s Vineyard trip. Downtowns are decorated, local shops and makers are in holiday mode, and several of the Island’s biggest holiday traditions happen within a few weekends.
This guide is specifically for planning a holiday-season visit between Thanksgiving and New Years, with the major dates to know, what’s open, where to shop, what to do, and a few things that are different about visiting the Vineyard this time of year.
📅 Pick Your Weekend: Major 2026 Holiday Dates
Thanksgiving Weekend | November 27–29
Vineyard Artisans Thanksgiving Weekend Festival • Chowder Cup • Small Business Saturday • other Thanksgiving-weekend programmingDecember 4–6 | Early December Holiday Weekend
Light Up Oak Bluffs • Vineyard Haven ’Tis the Season programming • holiday shopping, markets and other early-December eventsDecember 10–13 | Christmas in Edgartown
Four days of shopping, lights, markets, food, music and other downtown programming. Confirmed highlights currently include the Edgartown Lighthouse Lighting on December 11, the Holiday Faire and Christmas in Edgartown Parade on December 12, and the Art & Crafts Festival December 12–13.December 30-January 3 | New Year’s
Often the “last weekend of the year” for many seasonal spots, with an increasing number of restaurants offering New Year’s Eve dinners, parties and live music.
🎁 Holiday Markets + Shop Local
These are the longer-running shows, markets and shopping programs you can plan around. One-day pop-ups will be added to the event calendar below.
Featherstone 24th Annual Holiday Gift Show | November 7–December 16, 12–4p daily
Featherstone Center for the Arts, Oak Bluffs. Handmade work by Island artists including pottery, jewelry, knitwear, clothing, photography, ornaments, cards and more. Closed Veterans Day and Thanksgiving Day.30th Annual Vineyard Artisans Thanksgiving Weekend Festival | November 27–28, 10a–4p
Agricultural Hall, West Tisbury. The annual Thanksgiving market features work from Island artists and makers, including jewelry, ceramics, textiles, soaps, leather goods, woodwork and other locally made gifts.Golden Ticket Program | November 21–December 22
Shop, dine and stay at participating Island businesses and earn Golden Tickets toward the December 23 cash-prize drawing. Retail purchases earn a ticket for every $25 spent, with additional Gold Rush opportunities during the season.Vineyard Haven Holiday Shopping | December 4–6
Late-night shopping, downtown specials and pop-ups are planned as part of Visit Vineyard Haven’s ’Tis the Season weekend. A multi-day artist market at the MV Playhouse is also on the current 2026 schedule.Christmas in Edgartown Holiday Faire | December 12, 10a–3p
Edgartown Village Green. A Saturday market held during Christmas in Edgartown weekend.33rd Annual Christmas in Edgartown Art & Crafts Festival | December 12–13
Edgartown School. Opens Saturday at 10a and continues through Sunday afternoon.
✨ Lights + Festive Things to See
Lighting of the Edgartown Lighthouse | December 11, 5:30–6:15p
Memorial Wharf. Gather on the harbor for the Friday-night Christmas in Edgartown tradition, with the lighthouse lighting at 6p.Ocean Park Holiday Lights | 2026 schedule coming
One of the easiest free stops in Oak Bluffs once the gazebo and park are lit for December.Gatchell Family Light Display | 2026 schedule coming
148 County Road, Oak Bluffs. The family’s synchronized lights and music have become an Island holiday tradition.Donaroma’s Holiday Lights | 2026 schedule coming
Edgartown. Last year’s “Land of the Northern Lights” display ran nightly during the holiday season. I’ll add 2026 dates once announced.The Carnegie Holiday Display | 2026 details coming
Downtown Edgartown. Another easy indoor stop to pair with Main Street shopping once this year’s holiday programming is announced.
And honestly, just walking the three downtowns is part of it. Main Street Edgartown, Circuit Avenue/Ocean Park in Oak Bluffs and Main Street Vineyard Haven are all decorated for the season.
🍷 Where to Eat + Drink
The Vineyard is much quieter this time of year, but there are still plenty of places to eat. Expect fewer choices than summer and check hours before heading out, especially Sunday through Tuesday.
Good Year-Round Bets
Offshore Ale, The Attic, Red Cat Kitchen, The Lookout, Black Dog, Rockfish, The Maker, Bettini, are all known to decorate for the holidays for a cozier feel.
To try something new, Indigo, Pawnee House, 9 Craft Kitchen, and Restaurant Foster at Lambert’s Cove Inn are great options.
Holiday Specials + Pop-Ups
Brunches, Christmas cocktails, special dinners, live music, etc. will be added here once announced.
→ See the full MVacay Winter Restaurant Guide
🚢 Getting Here + Getting Around
The Steamship Authority from Woods Hole is the main year-round ferry to the Vineyard. If you’re visiting for a holiday weekend, bringing a car can be helpful since winter bus service is more limited and events may be spread across several towns.
If you’re coming without a car, Vineyard Haven is the easiest home base because the ferry arrives right downtown.
Is a day trip possible?
Yes, totally. If you’re coming just for the day, the Christmas in Edgartown Parade is probably the most ideal date. Walk off the ferry in Vineyard Haven, take the bus to Edgartown, and make a full day of the parade, shopping, food, and holiday events.
A ’Tis the Season day in Vineyard Haven is another great option, especially if you want an easier day trip without needing to travel far from the ferry.
🏨 Where to Stay for a Holiday Weekend
Edgartown: Best for Christmas in Edgartown and the most classic holiday atmosphere.
Oak Bluffs: Best for Light Up Oak Bluffs; much quieter than summer but decorated and walkable.
Vineyard Haven: Most practical year-round base, especially if arriving without a car.
I’ll keep updating this guide, and my weekly MVacay posts, as more holiday events are announced and details fill in.
If this is your first holiday season on Martha’s Vineyard, hopefully this gives you enough to pick a weekend, make a few plans, and start getting excited 🎄
