Saturday, November 28 · 1pm–3pm · Downtown Oak Bluffs, Oak Bluffs
On Small Business Saturday, the Saturday after Thanksgiving, Oak Bluffs offers horse-drawn carriage rides through downtown while downtown shops mark the day. The Chamber lists rides from 1 to 3 p.m. for 2026.
It's an easy add-on to a Thanksgiving weekend on the island, and a week ahead of Light Up Oak Bluffs on December 5.
In recent years rides have been $10 for adults and free for children under 12. Confirm this year's price before you go.
2023 and 2024: Oak Bluffs' holiday carriage rides were run by Sonnyside Rides, leaving from the loading zone in front of Eastaway.
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!
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.
Sources: MV Chamber holiday page · MV Times, Nov. 2024 · MV Times, Nov. 2023. 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.