Thursday, December 10 – Friday, December 11 · 3pm–7pm · Downtown Oak Bluffs, Oak Bluffs
The Oak Bluffs Holiday Stroll is two late afternoons and evenings of shopping downtown, with participating shops hosting pop-ups by local artisans. For 2026 it runs Thursday and Friday, December 10 and 11, from 3 to 7 p.m.
Those are the same days Christmas in Edgartown begins, so it's easy to do both: Oak Bluffs and Edgartown are a short drive or VTA bus ride apart.
It's a shopping event, so the shops set their own specials. Check the Oak Bluffs Association at obamv.com for this year's list.
2025: the stroll was new, held December 11 and 12 from 3 to 7 p.m. Participating shops included OSO, Toteally Yours, Craftworks, Curio, Sanctuary, Stefanie Wolf Designs, Lazy Frog, Jubilee, SEABAGS and Basics.
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.
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!
Sources: MV Chamber holiday page · MV Times, Nov. 2025. 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.