Rhinebeck's Holiday Season Has Been Rebuilt Around One Saturday in December

On December 20 last year, a polar bear danced in the parking lot behind Foster's Coach House. The Daily Freeman counted more than 100 people at "Dances with the Polar Bear." The Grumpuses and the Pocket Lady performed, carolers and musicians filled out the program, and the characters stayed afterward to mingle. That afternoon was all that was left of Sinterklaas. The full festival, with its Children's Starlight Parade and towering puppets, had been canceled three months earlier.

Sinterklaas won't happen this year either. What has grown in its place is smaller and spread across more hands. A volunteer nonprofit with a brand-new board, the Rhinebeck Area Chamber of Commerce and two local venues have each taken on part of the season. Most of their plans land on one date, Saturday, December 5.

What a free festival actually cost

The organizers' own website spells out the math. Sinterklaas was free to attend and cost about $125,000 to put on. It took close to 1,000 volunteers, including more than 350 performers and 350 volunteer puppeteers, and planning started the summer before. The site lists some of the fixed costs:

• About $10,000 for insurance
• About $10,000 in rentals, including porta-potties, barricades, stages and moving trucks
• A donation of about $10,000 to the village to cover police
• Food for performers and volunteers, puppet fabrication, costume materials, and printing for signs and programs

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 turning up year after year. That structure is where it broke. Creator and coordinator Jeanne Fleming's statement said the last hope of saving the 2025 festival fell through on the afternoon of Friday, September 19. Tariffs had made things worse. The stars are made in India to benefit an orphanage, and their lights come from China. Their price had nearly tripled, and star sales covered one-fifth of the budget. Arts grants had also been cut back or eliminated. The Daily Catch reported the cancellation on September 24, 2025.

Last December, the other traditions went dark too

Losing Sinterklaas would have been easier if the rest of the season had held up. It didn't. In early December 2025, The Daily Catch reported that Doughboy Park would have no holiday tree and no lighting ceremony. Mayor Gary Bassett said the volunteer Holiday Tree Lighting Committee, which had held the ceremony the year before, had disbanded. That left no organization responsible for the tree. The same report said village officials were discussing whether the Rhinebeck Jewish Center's menorah would keep its spot on municipal property after 2025.

This year, two more fixtures dropped off the calendar. The Dutchess County Fairgrounds' Wonderland of Lights won't return in 2026. The Daily Catch reported that founder Tammy Peters cited staffing issues. Rhinebeck Bank, which used to host its own tree lighting, is also skipping 2026 because of liability concerns.

That's three separate December traditions, each run by a different group, gone in two years. None of the endings were connected. Together, they emptied out the calendar.

A revived nonprofit stepped in

The rebuilding started at a Village Board meeting in late August. The Daily Catch's account quotes Victoria Polidoro, a board member of Rhinebeck Hometown Holiday Tree Lighting, telling trustees: "There was nothing big last year." With no Sinterklaas and no Fairgrounds light show, she added, "I just think we need some joy in the winter months."

This is the same organization that ran tree lightings in earlier years, including 2024. It now has an entirely new board made up of Polidoro and fellow Rhinebeck residents Sara Capozzoli and Lindsay Little. Here's what the trustees approved, according to the outlet's report:

• Date and hours: The evening of December 5, running roughly 5 to 8 p.m.
• Location: The Village municipal parking lot, with the tree and menorah expected near the Doughboy statue
• The tree: Temporary, and donated and paid for by the organization, not the Village
• Expected crowd: About 200 people, according to the event application
• Planned extras: A few food trucks, and possibly craft vendors and a choir

The vote was unanimous. One condition came with it: organizers had to return at least 45 days before the event with a final layout showing how the lot would be used. That means the exact arrangement in the lot was still being worked out after the August vote. Past celebrations have featured a parade, Santa lighting the tree, a family photo area and a DJ. Those details come from earlier years and haven't been announced for 2026.

"I love the idea of actually having a holiday event this year," Trustee Jennifer Neufeld said, as The Daily Catch reported. Polidoro also said she has been working with Rabbi Hanoch Hecht of the Rhinebeck Jewish Center to make the evening "all inclusive." The Daily Catch wrote that lighting both a tree and a menorah appears to settle last year's question about the menorah's placement, at least for this season.

The Chamber built its new event onto the same day

In August, Polidoro told trustees the Chamber wasn't planning a holiday event of its own. Local business leaders were discussing a window-display contest that could be tied to the December 5 celebration. By mid-September, that idea had grown into a named event. The Rhinebeck Area Chamber of Commerce now lists a new Holiday Shop Crawl, Carolers & Window Display Competition. It will run on the first Saturday of December, which is December 5 this year.

The Chamber's Victorian Traditional Carolers will visit shops and other spots around the village, ending with a fireside finale. The listing also includes the Tree and Menorah Lighting, crafts and other family activities. The page doesn't yet give contest entry rules or name the participating shops. The same page notes that the Chamber's holiday lights strung through the center of the village are part of the season too.

So a nonprofit that pays for its own tree and a business association with a new shop crawl have both chosen the same Saturday. That puts a carolers' route, decorated windows and a parking-lot lighting within a few blocks of one another on one evening.

The season around it

December 5 is the busiest day, and a few venues fill out the weeks around it. Here's what's on the calendar, and what isn't, as of late October.

Wilderstein carries more weight than usual this year. Its tours run every weekend from the Friday after Thanksgiving through December 27. That makes it the only event on the list that lasts the whole season and isn't tied to a single evening. A family could spend all of December 5 in the village, starting at the CENTER in the morning, following the carolers through the afternoon and finishing at the lighting.

Smaller, and spread across more people

Compare the scale. Sinterklaas needed close to 1,000 volunteers and a $125,000 budget, and about half of that budget depended on benefactors. This year's lighting has a three-person board, a donated tree and an expected crowd of about 200. The Chamber's event uses the carolers and storefronts the village already has. No single donor holds up the season anymore. If one piece falls through, the others can still go on.

Rhinebeck Hometown Holiday Tree Lighting is still looking for sponsors, donations and volunteers. Polidoro has said the group is "very open" to working with any organization that wants to take part. Anyone interested can email [email protected].

At Fresh Air Realty, we follow the small decisions that shape a place: board votes, volunteer committees, a parking lot set aside for one December evening. If you own in Rhinebeck and want to talk about how the village is changing, Joseph Satto is happy to meet, upstate or in the city.