Oak Bluffs celebrates the season downtown, around Healey Square and Circuit Avenue: a tree lighting, horse-drawn carriage rides, a holiday stroll and small-business shopping events.
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.
Join us in Healy Square for Santa, live music, caroling, cocoa, and the tree lighting at 6:30 PM. Please note that this event has moved to a new date this year!
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.
Still checking off your Christmas list? Find a little last-minute magic in Oak Bluffs, with shops open late for gift shopping, wrapping, and festive refreshments!
Twelve months of island photography, from Edgartown Harbor to Gay Head Light. Matching notecards too.
Most Oak Bluffs events are centered on the downtown. Event details come from the Oak Bluffs Association, the Martha's Vineyard Chamber of Commerce and each organizer, so confirm times before you go.
Last checked Thursday, November 12. Oak Bluffs on a map.