Oak Bluffs Starts the Holidays on a Thanksgiving 5K, and the Tree Comes Nine Days Later

"Light Up Oak Bluffs actually grew out of some very simple community traditions: neighbors and local families gathering in Healey Square, shops staying open a little later, and volunteers decorating downtown together." Jen Adamson, then interim director of the Oak Bluffs Association, gave that account of the event's roots to The MV Times last November, right after the 2025 tree went up.

That tree went up on the Saturday after Thanksgiving. The 2025 Light Up Oak Bluffs was on November 29, and the Vineyard Gazette calendar listed the tree lighting for 6:30 p.m. that evening. This year the Oak Bluffs Association has scheduled Light Up Oak Bluffs 2026 for Saturday, December 5.

Moving it one week splits what used to be a single long weekend into two separate openings. Thanksgiving weekend now starts with a road race and a library morning. December 5 picks up the tree, the library's fullest holiday afternoon of the season and the first full day of Hanukkah. The two dates are nine days apart, and the town calendar fills the days in between.

Thanksgiving Morning Runs the Town on Foot

The first holiday event in Oak Bluffs this year is the OB Turkey Trot, a 5K road race on Thursday, November 26. The race registration page lists an 8:30 a.m. start and gives Inkwell Beach House, 9 Oak Bluffs Ave, as the event's place. The race raises money for the Oak Bluffs School eighth grade, and the Town of Oak Bluffs calendar lists it for Thanksgiving Day too.

Registration costs $22.20 including a $2.20 fee, and online sign-up closes Wednesday, November 25, at 10 p.m. Anyone who decides on Thanksgiving Eve still has a few hours to register.

The course covers a good share of town. As published by the organizers, it goes like this:

1. Start in front of the police station.
2. Turn up Circuit Avenue and follow it to Wing Road, heading toward the Firehouse.
3. Turn right onto County Road.
4. Turn right onto Vineyard Avenue at the end.
5. Turn left onto Dukes County Avenue and follow it until it ends at the harbor.
6. Turn right and run back up to Chowder Company.

In about three miles, runners go from the downtown commercial street out through the residential roads and back to the water. For anyone who isn't running, Circuit Avenue early on and Dukes County Avenue near the harbor are where most of the field passes. The MV Times Grapevine column summed up the morning this way: "For the runners among us, a festive start to the day; for the rest of us, a very good reason to cheer."

The Saturday After Thanksgiving, Now Without the Tree

In 2025, Saturday, November 29 was Light Up day. This year the matching Saturday, November 28, is Small Business Saturday, which the same MV Times column describes as a nudge to put holiday dollars to work in Island shops.

In Oak Bluffs, that Saturday's scheduled programming happens at the Oak Bluffs Library. Its calendar lists a Cranberry Celebration from 10:30 a.m. to noon, with hands-on activities, experiments, building projects and trail-mix making. The morning also has Tech Help from 10 a.m. to noon and Baby and Toddler Storytime at 10:15. The All Ages Chess Club meets from 2 to 3:30 p.m.

The Friday before is busy elsewhere on the Island. Felix Neck holds its free Fall Festival on November 27 from 10 a.m. to 2 p.m., with hayrides, live music, wildlife demonstrations, wreathmaking and crafts. The Vineyard Artisans Thanksgiving Weekend Festival is at the Ag Hall on November 27 and 28, from 10 a.m. to 4 p.m. both days. With Light Up off this weekend, an Oak Bluffs household can spend the Friday at those events and the Saturday morning close to home without one cutting into the other.

The Week That Builds to December 5

Between Thanksgiving weekend and Light Up, the library calendar picks up again with programs aimed squarely at the season. Here is the run from the first Wednesday in December through the tree-lighting Saturday, using the library's posted schedule and the OBA's date.

Gingerbread House Making requires preregistration, and it is the one item on that Saturday that can fill up before the day arrives. The staged reading of A Christmas Carol is at 7 p.m. that same evening, so a family could have one child's afternoon at the gingerbread table and the whole household's evening on Dickens without leaving town.

The calendar also lines up with Hanukkah. According to Chabad.org, Hanukkah 2026 begins at sundown on Friday, December 4. That makes Saturday, December 5 the first full day of the holiday, so this year Light Up Oak Bluffs shares its date with the first nights of Hanukkah. Last year's Thanksgiving-weekend date did not.

On the Thursday before Thanksgiving, the day this post goes out, the library also runs a Book Tasting Event, styled as the Read-A-Latte Cafe, from 3:30 to 5:30 p.m.

Who Puts the Tree in Healey Square

The December 5 date is new. The way the event gets built is not, and Adamson's account in the 2025 MV Times piece named the hands behind it. "It's really just a bunch of local folks doing their part," she said. The Friends of Oak Bluffs volunteered to make the big red bows for the Healey Square tree. The Highway Department brought in the tree itself, and Mahoney's arranged it. Stefanie Wolf ran her Snowflake Scavenger Hunt, placing paper snowflakes in participating shops so children could get passports stamped as they explored town.

The town's 2025 listing put the tree lighting, horse-drawn carriage rides and hot cocoa in Healey Square. Adamson described the event as one that had grown over the years into a weekend with carriage rides, holiday markets, cocoa, music and more businesses joining in, while keeping its focus on local families. Those are last year's details. The 2026 program lives on the OBA's Light Up page.

Oak Bluffs volunteers have been working on the town's trees in another way this fall. On October 17, the Oak Bluffs Tree Stewards and their volunteers planted ten trees in Naushon, Nashawena and Sunset Lake parks. In a thank-you letter published in The MV Times, the group said it was seeking Community Preservation Act funds to plant 60 more over three years. The ten new trees stand in those three parks now, ahead of the Healey Square tree's arrival for December 5.

If your Oak Bluffs home is closed for the season and you plan to come back for the Turkey Trot or for December 5, Match Point Properties can open, check and ready your house around either weekend, so it is warm and lit when you arrive and secured again after you leave. Request a Local Consultation and we will plan your visits around the town calendar.