Oak Bluffs kicking off the holiday season

The original painting by Jacob Knight is on permanent display at the Oak Bluffs library. —Courtesy OB Association

The Oak Bluffs Association will launch the annual “Light Up Oak Bluffs” Thanksgiving weekend celebration in downtown Oak Bluffs on Saturday, Nov. 25. 

There will be an array of shopping, dining, and activities, capped by the annual Holiday Tree Lighting at 6:30 pm, followed by Santa’s arrival.

Throughout the day, merchants and the Oak Bluffs Association (OBA) will offer activities ranging from cookie decorating at Offshore Ale Co. to games involving reindeer in Ocean Park, to photo ops with Santa’s elves in Healey Square. 

The Holiday Open Market will take place from 1 to 3 pm at the Strand Theatre, with arts, crafts, jewelry, and more from local artisans. Oak Bluffs School holiday art will be on display in the windows of the Corner Store, and the tree in Healey Square will be decorated with OBA member ornaments. The Vineyard Gazette’s holiday-decorated antique truck will be selling merchandise. Local musicians Aly and Paryss will perform holiday music, and back this year are horse-drawn carriage rides by Sonnyside from 2 to 5 pm, starting at Eastaway. Children under 12 ride free, and it’s $10 per person. The Santa Sweepstakes returns at participating retailers, so shoppers can make a purchase and get a free chance to win a prize from that merchant. 

The annual Tree Lighting will take place at 6:30 pm, preceded by caroling in Healey Square with Rose Guerin and Sean McMahon. There will be free hot cocoa, sponsored by Santoro Hospitality, at the Pawnee House; and more sweet treats from Enchanted Chocolates, candy canes from Basics, and an Oak Bluffs tradition, reindeer antlers, provided by Stefanie Wolf Design. Thanks to Rockland Trust, there will be popcorn and light-up necklaces. Immediately after the tree lighting, Brian Weiland and co. will summon Santa’s arrival by singing in front of Offshore Ale. Santa will arrive via Oak Bluffs fire truck, with lights flashing — lots of fun activities for families and children.

“Light Up Oak Bluffs” is sponsored in part by the generosity of Martha’s Vineyard Bank and the Friends of Oak Bluffs. The Friends are offering “Peace on Earth,” Jacob Knight’s wonderful print originally featured on the cover of Yankee Magazine. The numbered posters are available for sale at da Rosa’s for $30, as well as notecards, 10 for $20. Both can also be ordered by visiting friendsofoakbluffs.org

The original painting by Jacob Knight is on permanent display at the Oak Bluffs library. 


  1. Really too bad for the islanders who travel for Thanksgiving. Traditionally the tree light lighting was on a Wednesday after Thanksgiving when most island kids would be here to enjoy it.

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