Light up Oak Bluffs

Ocean Park has a magical glow during the holiday season. — Ralph Stewart

Get the holiday season going with a number of fun events in Oak Bluffs, including open markets, a visit from Santa, horse drawn carriage rides, caroling, and more.

On Nov. 25, from 10 am to 3 pm, the Oak Bluffs Holiday Open Market at The Strand theater will be available for folks to get all their holiday shopping done. Peruse a variety of local artisans and vendors, and enjoy a visit from Santa and food provided by Winston’s Kitchen from 11 am to 1 pm. From 4:30 to 6 pm, get dressed up in your holiday best and participate in the first ever Stumbling Santa Fun Run — a short two mile route that starts at the Ritz and ends at Dos Mas. Pace yourself! 

On Nov. 26, from noon to 2 pm, come out and take a picture with Santa in Post Office Square. Donations to the Oak Bluffs Association are welcome. Also from noon to 2 pm, Juice by the Sea invites the community for some hot cocoa and cookies. From noon to 8 pm, write your holiday gift wish list down and hand it in to Santa — sponsored by Island Outfitters and Basics. From 2 to 3 pm, join Lisa Knight in Ocean Park for festive sack races and various other fun reindeer games (you could even win a prize). Sonnyside Rides will provide horse drawn carriage rides from 2:30 pm to 5:30 pm, sponsored by Crossland Landscape and the Ritz, cash donations are accepted. From 5 to 6:30 pm, carolers will bring some holiday cheer to Eastaway Clothing on Circuit Avenue, then from 6 to 7 pm Rockland Trust sponsors an event offering hot cocoa and light up necklaces. 

The most anticipated event of the Oak Bluffs holiday happenings features a festive tree lighting in Post Office Square and the electric trees in Ocean Park will also be illuminated. From 6 to 7 pm, Enchanted Chocolates will be selling delicious treats and folks can also enjoy carolers, live music, and hot cocoa in the square. Santa will arrive by fire truck at 6:30 pm. At 8 pm, pick out your ugliest holiday sweater and head to the Ritz for an ugly sweater contest. Judging begins at 8:30 pm. The evening ends with a special screening of “The Grinch” at The Strand at 8 pm. 

There’s plenty to do for the holiday season in Oak Bluffs, so bring your friends, family, and loved ones to experience a special town tradition.