On Christmas Eve on the Woodstock Village Green, Santa waits for the bus. Caroling starts at 5 p.m. Santa's arrival is set for around 5:30, but first the eastbound and westbound Trailways buses have to clear town. Then Woodstock police close the road and the Woodstock Fire Department opens a path. Hudson Valley One reported that the planning covers everything from crowd control to FAA clearances.
The next afternoon, a different group of volunteers serves a free holiday dinner that the town nearly lost. Volunteers put both events together by hand in the weeks before Christmas. With the holiday about five weeks away, that means right now.
Santa yields to the Trailways bus
Santa has been arriving in Woodstock on Christmas Eve since 1932. The Woodstock Christmas Eve Committee runs the evening. It keeps one rule for the entrance: it changes every year, and only a handful of volunteers know the plan ahead of time.
Past entrances show how far the committee will go. Hudson Valley One has recalled a floating VW Bug, a rooftop, a cannon and a dove. In 2023, the Grinch tried to leave town with Santa stuffed inside a big wrapped gift box. Woodstock police arrested the Grinch, and Santa popped out of the box in a burst of confetti, according to the paper's coverage that year.
The entrance takes months. The committee says a "small army of volunteers" is recruited many months ahead to build the Santa float and set up the lights and sound. Rebecca Turmo owns Jean Turmo Ltd. and sits on the committee. In 2025 she was in her second year helping design Santa's arrival and the float, and she gave away nothing about it ahead of time.
Last year, for the first time, the committee got and decorated the tree on the Green itself. Bob Bloomer of LA Tree picked the tree up from a Woodstock donor and set it up. Committee member Mary Smith made the star on top. Blue flags with doves also went up along Mill Hill Road and Tinker Street in 2025. Turmo bought them herself, and American Legion Post 1026 hung them on its own flagpoles. The music has two parts: the traditional carolers in front of the Woodstock Reformed Church, and the Rock Academy playing as Santa arrives.
Four hundred stockings, packed by hand
Much of the committee's work goes into what gets handed out. As of the 2025 season, the committee hands out these each year:
| Item | Yearly count | Who receives it |
|---|---|---|
| Stockings | 400, packed by hand | Children at the Green |
| Cheer bags | 230 | Delivered to names suggested by town officials and community members |
| Dinner baskets | A couple dozen | Delivered to households |
Smith told Hudson Valley One that stocking-packing is "an afternoon event with probably 10 to 20 people making it work," run like an assembly line. Every cheer bag holds an ornament and a pair of fluffy anti-skid socks.
All of it is paid for with donations. "Although the town allows us to do it, we don't have any financial support from the town," Smith told the paper. "Nobody's paid." The committee's website has a QR code for donations. Checks payable to Woodstock Christmas Eve have also been accepted by mail or in person at Mid-Hudson Valley Federal Credit Union, 85 Mill Hill Road.
The next afternoon, a dinner that nearly disappeared
Christmas Day has its own tradition with its own crew. The Woodstock Chamber of Commerce & Arts describes it as decades of Woodstockers gathering at the Community Center on December 25 to share food, songs and stories. The Chamber calls it a place to land on a day when "regardless of beliefs or religion, many feel alone."
Community member Roxie Dawn started the dinner, and Toni Wiedenbacher guided it for years. A Hudson Valley One account shows how flexible it has had to be. One year the Community Center was under renovation, so the party moved to Overlook United Methodist Church at 233 Tinker Street and ran from 1 to 4 p.m. with music, food and gifts for children.
The pandemic ended the dinner. In 2024 the Chamber brought the old team back together, led by what it calls "some of Woodstock's next generation." Servers, carvers, home cooks, singers, songwriters and storytellers returned, and dinner was served again in 2024 and 2025. On November 1, 2026, the Chamber posted that the dinner will return on December 25, 2026, and that it is still free.
What the dinner asks for, and why refrigerators are on the list
Christmas Eve mostly needs money and packing hands. The dinner is a potluck, so it needs more kinds of help. The Chamber's 2026 call asks for:
- Volunteers, including people to join the service team
- Donations
- Gifts for kids
- Kitchens and chefs
- Storage and refrigeration
- Food, built around a baseline menu with room for what people want to bring
Kitchens and refrigeration are on the list because of how a potluck works. A dinner made from many households' cooking needs places to prep and hold food before December 25. The Chamber has one more request: guests should check with the meal curation team and bring food they can eat themselves, so that food allergies and other concerns are covered. The Chamber posts updates, asks and ways to help on its holiday dinner page.
Who has already stepped in
The Chamber's thank-you list for the revived dinners reads like a list of the town's own businesses and services. It names farm markets Adams Fairacre Farms and Sunfrost Farms, and bakeries Meredith's Bakery and Overlook Bakery. It thanks Alba's Kitchen, Dharmagirl's Kitchen, Garden Cafe, Joe Bones, Oriole9, Colony Cafe Woodstock and Station Bar & Curio. Houst's Hardware and Tinker Toys are there too. So are Family of Woodstock Hotline, Woodstock's Good Neighbor Food Pantry, Woodstock Mutual Aid, Seasoned Gives, Ulster Savings and the Town of Woodstock, along with Toni Wiedenbacher and a handful of individual neighbors.
A hardware store and a toy shop share that list with bakeries, a food pantry and a mutual aid group. Both holiday days lean on people who live and work along Tinker Street, Mill Hill Road and Route 212.
The weeks in between
The stockings, the float and the dinner all come together in the same stretch of December when Woodstock's stages are busiest. Here is what's on the calendar between now and the two volunteer days:
| Date | Event | Where |
|---|---|---|
| Through Dec. 13 | "The Four Seasons" exhibition | Playhouse Gallery |
| Through Jan. 3, 2027 | "Feathered Friends: A Woodstock Aviary" | WAAM, 28 Tinker St. |
| Sat., Dec. 5 | Cosmic Charlie Brown Christmas, shows at 4 and 7 p.m. | Bearsville Theater |
| Sun., Dec. 6 | Tony Trischka's Holiday Show, 8 p.m. | Bearsville Theater |
| Tue., Dec. 8 | The Wood Brothers with Tyler Ramsey, 7 p.m. | Bearsville Theater |
| Dec. 11 to 13 | A Christmas Carol: The Musical | Woodstock Playhouse |
| Dec. 15 and 16 | Gillian Welch and David Rawlings, 8 p.m. | Bearsville Theater |
| Thu., Dec. 24 | Caroling and Santa's arrival | Village Green |
| Fri., Dec. 25 | Holiday Community Potluck Dinner | Organized by the Woodstock Chamber |
The Cosmic Charlie Brown Christmas at Bearsville Theater plays the music of Vince Guaraldi and the Grateful Dead. Its two Saturday shows fit easily around an afternoon of errands. The Playhouse production comes from students and families of the New York Conservatory for the Arts, so it is a local show as much as a holiday one. The aviary show at the Woodstock Artists Association & Museum runs past New Year's, so out-of-town guests can still see it after both volunteer days are over.
Christmas Eve falls on a Thursday this year and Christmas Day on a Friday. That puts the Village Green gathering and the community dinner on back-to-back evenings at the start of a long weekend. For both events, most of the packing, cooking and building happens before then.
At Fresh Air Realty, we work with plenty of people who split their weeks between Brooklyn and Ulster County. December is when that line blurs the most. If you're upstate this season and want to know where your help would do the most good, from a stocking-packing afternoon to a spare refrigerator for the Christmas Day dinner, reach out and we'll help you get connected.
