Saturday, December 5 · 6:30pm · Healy Square, Oak Bluffs
Light Up Oak Bluffs is the Oak Bluffs Association's kickoff to the holiday season, centered on the town tree in Healey Square. The day brings shopping, kids' activities and carriage rides downtown, then carols and the tree lighting in the evening, with Santa arriving on an Oak Bluffs fire truck.
It has usually been held on Thanksgiving weekend. For 2026 the Martha's Vineyard Chamber of Commerce lists it on a new date, Saturday, December 5, with the tree lighting at 6:30 p.m.
Carriage rides have run from in front of Eastaway in recent years, at $10 for adults and free for children under 12.
The Friends of Oak Bluffs make the tree's red bows, and the town's highway department brings in the tree.
The Oak Bluffs Association posts the day's schedule at obamv.com.
2025: Circuit Avenue shops opened at 10 a.m., Santa arrived at the Strand Theatre at noon, and the tree was lit at 6:30 p.m. with carols and hot cocoa. Kids collected stamps in a Snowflake Scavenger Hunt passport at participating shops.
2024: Santa photos in Healey Square from noon to 4, Reindeer Games for kids in Ocean Park, carriage rides from 1 to 4, caroling at 6 and Santa's fire truck at 6:35.
2023: cookie decorating at Offshore Ale, reindeer games in Ocean Park, a holiday market at the Strand Theatre, and carriage rides before the 6:30 lighting.
Twelve months of island photography, from Edgartown Harbor to Gay Head Light. Matching notecards too.
Celebrate the holiday season while supporting Island artists and Featherstone! The perfect holiday shopping destination with gifts for everyone (and yourself) — handmade creations including paintings, photography, pottery, crafts, jewelry, knitwear, clothing, accessories, ornaments, cards, calendars and stocking stuffers. Buy local and support local artists all while supporting Featherstone as well! 'Tis the season for supporting the arts community!
Join us for the annual Oak Bluffs School Turkey Trot! Runners and Walkers of all ages are welcome! Come burn some calories before you feast!
Horse-drawn carriage rides around town for Small Business Saturday.
Our second annual Holiday Stroll! Participating shops and restaurants throughout downtown Oak Bluffs will host artisan pop-ups, crafts, refreshments, holiday music, and festive shopping. 3-7PM both nights.
Sources: MV Times, Nov. 2025 · Vineyard Gazette, Nov. 2025 · MV Times, Nov. 2024 · MV Times, Nov. 2023 · MV Chamber holiday page. Past-year details are from local news coverage; this year's plans can differ.
Details come from the organizer and can change. Confirm before you go. Last checked Thursday, November 12. Spot a mistake? Tell us.