Who Keeps Rhinebeck's Winter Calendar Running?

"It is hard to believe that something as unique and beloved as Sinterklaas could fall casualty to lack of money, but that is the case." Jeanne Fleming, Sinterklaas creator and coordinator, wrote that in the committee's statement canceling the 2025 festival. The Times Union reported it under a headline about tariffs.

The traditions that have left Rhinebeck's winter calendar since last fall all depended on a small group of volunteers or a staff, and that group ran out. The events still confirmed for November and December are the ones with an organization behind them. In December, Village voters will decide whether to give one of those organizations a new reason to stay.

A free parade carried a $125,000 budget

The festival's own accounting explains why Sinterklaas was fragile. The committee puts the cost of the free, day-long event at about $125,000. That included roughly $10,000 for insurance, $10,000 for rentals such as stages, barricades and moving trucks, and a $10,000 donation to the Village to cover police.

Paying for it took close to 1,000 volunteers in all. More than 95 started work the summer before, alongside more than 350 performers and 350 volunteer puppeteers. About half the money came from small donors, a few grants and sales of the illuminated Sinterklaas stars. The rest depended on one or more benefactors appearing each year.

The star sales covered about one-fifth of the budget. The committee said the stars are made in India to benefit an orphanage and the lights in China, and that both nearly tripled in price. Arts grants had also been cut back. On Friday, September 19, 2025, the committee's last funding option fell through and the festival was canceled after 26 years. The Times Union also noted that the 2024 parade had already been replaced by a smaller program of dance performances and dioramas by local artists.

Eleven months of subtractions

The other losses came one after another, each for a slightly different reason, and each traces back to a group that could no longer staff or fund the work.

1. September 19, 2025. Sinterklaas canceled after its final funding effort fell through.
2. December 4, 2025. The Daily Catch reported that Mayor Gary Bassett said there would be no holiday tree and no tree-lighting in Doughboy Park that season. The volunteer Holiday Tree Lighting Committee had disbanded, which left no organization responsible for the tradition.
3. December 20, 2025. The Sinterklaas crew put on "Dances with the Polar Bear" in the Foster's Coach House parking lot. The Daily Freeman counted more than 100 people for the Polar Bear, the Grumpuses, the Pocket Lady, carolers and percussionists.
4. August 14, 2026. Hudson Valley One reported that the Wonderland of Lights, the drive-through Christmastime light show, had closed its Rhinebeck show after five years. The organizers gave staffing as the reason.

The Polar Bear afternoon is the clearest example. The committee wrote that once people in the village asked for something to fill the empty December, the Polar Bear said yes first. Stage managers, musicians, dancers and bell ringers followed, and the crew came together within hours. The Bender family and Foster's gave the space. Rhinebeck had the people and goodwill for a two-hour gathering. It no longer had the $125,000 structure needed for a festival filling every corner of the village.

The Daily Catch also noted that the business corridor was lit for the holidays last December even without a tree.

The same math, at the firehouse

The Rhinebeck Fire Department runs on the same kind of volunteer roster, and its work goes on all year. The department lists 60 active members and calls itself a 100 percent volunteer organization. It answers more than 1,150 fire and EMS calls a year and describes itself as the busiest department in Battalion 1, which covers northwestern Dutchess. It is recruiting for every service it offers.

Those 1,150 calls work out to about 19 per active member each year. The time commitment is substantial. The department lists 71 hours of training for an ambulance operator and 183 hours for an EMT, with training and equipment provided free. EMS is part of the same organization. The department's history says the former Rhinebeck Rescue Squad joined it in 1970.

In his October message, Mayor Bassett wrote that Rhinebeck is "one of many municipalities facing challenges in recruitment of volunteer firefighters and EMS workers." The Village's response is a Length of Service Award Program, known as LOSAP. The Village describes the proposal this way:

• A defined contribution plan that works like an IRA, not a pension.
• The Village would contribute up to $1,200 a year to each qualifying volunteer's account, paid out at age 65.
• To earn credit for a year, a volunteer needs 50 points from calls, drills and training.
• Current volunteers could receive credit for up to five years of past service if they qualify in the program's first year.
• Auxiliary, social-only and life members are not eligible under the department's bylaws.

The Village's reasoning, in its own words, is that "a volunteer department costs residents far less than a career, paid department." The Board of Trustees passed Resolution #10132026-01 on October 13, and the proposal goes to a special election on Tuesday, December 8. Polls are open from noon to 9 p.m. upstairs at Village Hall, 76 East Market Street. If it passes, the program would take effect January 1, 2027. The Village Clerk takes questions at 845-876-7015, option 3.

Village Treasurer Karen McLaughlin's year-end report, quoted in the same message, includes "the labor force is changing" among the Village's challenges. The firehouse ballot question and the empty spot in Doughboy Park come from the same constraint.

What is confirmed, and who stands behind it

Every event on the confirmed list below has an organization behind it, with a board, a staff or a box office.

Wilderstein's holiday tours cost $20, paid on arrival, and the house is closed on Christmas Day. Tours have limited space, and the site suggests arriving about 15 minutes early. Under its 2026 schedule, the farmers market runs outdoors on Sundays from May 3 through December 27. That means the volunteer board running it is staffing the municipal lot through the last weekend of the year.

The dates still open

Three traditions have no published 2026 date yet. The Sinterklaas website still shows the 2025 cancellation statement and the Polar Bear invitation. The Rhinebeck Area Chamber of Commerce event calendar lists no December date for the festival or a successor. The Doughboy Park tree has no announced organizer since the committee disbanded.

The third is newer. The Daily Catch's event listing billed the Chamber's Holiday Carol Crawl as a "first annual" event on December 13, 2025. Carolers visited Village shops, starting at Foster's Coach House and ending with a fireside finale at the Beekman Arms. Whether it becomes a second annual event depends on the same thing as every other open date this winter: whether an organization takes it on and gets enough people to show up.

Foster's lot hosted the Polar Bear, and the Carol Crawl started there. When Sinterklaas went quiet last year, the committee noted that the village was dark on Sinterklaas evening except for the lights at Foster's Coach House. For the past year, Rhinebeck's December has depended on a few institutions willing to give it space, and on whether volunteers fill that space.

The Hudson Valley Team at Compass has followed this village through more than a century of seasons. We keep track of how the firehouse, the market board and the people at Foster's keep it running. If you'd like to talk through what that continuity means for a Rhinebeck property you own or are considering, Start a Confidential Consultation.