Last December 20, more than a hundred people stood in the Foster's Coach House parking lot to watch a polar bear dance. The Grumpuses performed, the Pocket Lady made the rounds, and carolers and percussionists filled the gaps. The Daily Freeman reported that the afternoon drew roars of cheers.
The gathering was a stand-in for Sinterklaas. The festival used to fill the village on the first Saturday of December and draw thousands, and it had just been cancelled for the second year in a row.
This year the first Saturday of December falls on December 5, and the village has a full day planned again. No single festival is coming back to fill it. A few local groups, each working at a scale it can manage, are splitting the day among them.
Why One Festival Couldn't Hold the Day
Sinterklaas was free to attend and expensive to put on. According to the organizers' own site, each year took about $125,000 and close to 1,000 volunteers, including more than 350 performers and 350 volunteer puppeteers. Insurance ran about $10,000, rentals another $10,000, and a donation of about $10,000 went to the village to cover police.
About half of that money came from small donors, a few grants and sales of the illuminated Sinterklaas stars. The other half depended on one or more benefactors turning up each year.
That model gave out in stages. The Daily Freeman reported in July 2024 that the festival would not run that year unless organizers could "pull a rabbit out of a hat." In 2025 the committee tried again. Its last funding option fell through on September 19, and creator and coordinator Jeanne Fleming announced the cancellation. Her statement said tariffs had nearly tripled the price of the stars, which are made in India, and of the lights, which are made in China. Star sales had covered about a fifth of the budget.
For 2026, The Daily Catch reported in August that a local event organizer had checked with Fleming and been told the festival will not take place this year.
The Other Holiday Fixtures Dropped Out Too
Sinterklaas was the biggest loss, but other December events went quiet over the same stretch:
- Wonderland of Lights, the drive-through light show at the Dutchess County Fairgrounds, closed its Rhinebeck show after five years. Its email to followers blamed staffing issues, Hudson Valley One reported on August 14. In 2024 it ran from November 28 through December 29.
- Rhinebeck Bank, which used to host its own tree lighting, does not plan one this year because of liability concerns, according to The Daily Catch.
- The village tree lighting did not happen in 2025. The nonprofit behind it had disbanded, and whether the village would keep a menorah on municipal property after 2025 was an open question.
That is why December 2025 ended up with a single afternoon in a parking lot.
A New Board Brings the Tree Back to the Municipal Lot
The village tree lighting has come back first. Rhinebeck Hometown Holiday Tree Lighting is the community nonprofit that ran tree lightings in past years, including 2024. It has been revived with an entirely new board: Victoria Polidoro, Sara Capozzoli and Lindsay Little. Polidoro took the plan to the Village Board in August, and The Daily Catch reported what she said there:
"There was nothing big last year. I just think we need some joy in the winter months."
Trustees approved the evening of December 5 unanimously. Their condition was that organizers come back at least 45 days ahead with a finished plan, including a detailed layout of the municipal parking lot. The application estimated a 5 to 8 p.m. event with about 200 people. The plans described at that meeting include:
- A temporary Christmas tree, donated and paid for by the organization, not the village, set up near the Doughboy statue in the municipal lot
- A Hanukkah menorah lit at the same event. Polidoro said she had been in touch with Rabbi Hanoch Hecht of the Rhinebeck Jewish Center to make the celebration "all inclusive."
- A few food trucks, and possibly some craft vendors and a choir
With a menorah in the plans, the question left hanging after 2025 is settled for this holiday season.
An event for 200 people with a borrowed site and a donated tree is a very different job from a $125,000 festival that needed a benefactor every year. A three-person board can run it.
The Chamber Takes the Afternoon
The afternoon belongs to the Rhinebeck Area Chamber of Commerce. Its Holiday Shop Crawl, Carolers + Window Display Competition is free. The Chamber's Victorian Traditional Carolers sing from 3 to 5 p.m., and participating shops offer treats, special offers and family activities all day.
The Chamber calls the crawl new. Last year's edition was on December 13, and the 2026 version moves to the first Saturday of December. The Chamber's own events page says this year's program will also include a Tree and Menorah Lighting, plus crafts and other family activities.
The 2026 route is listed as TBA. For a sense of the walk, here is the 2025 lineup by street:
| Stretch | 2025 participants |
|---|---|
| Montgomery Row | Foster's Coach House, Paper Trail, Oblong Books, Pause Dog Boutique, Gigi's Trattoria, Hammertown, J. McLaughlin |
| Garden Street | Twin Tides Tattoo, High Score Arcade, ME Hair Studio |
| East Market Street | Rhinebeck Mercantile, Winter Sun Summer Moon, Land of Oz Toys, Pegasus Shoes, Rhinebeck Artist's Shop, John Jack's |
| West Market Street | Rain Spa, La Tua Bella Salon |
Last year's crawl started at Foster's Coach House and ended with a fireside finale at the Beekman Arms. Foster's is also where the polar bear danced last December.
December 5, Start to Finish
The CENTER for Performing Arts at Rhinebeck, at 661 Route 308, adds two shows to the day. Put together, the first Saturday of December looks like this:
| Time | What | Where | Cost |
|---|---|---|---|
| 11 a.m. | A Christmas Carol, Saturday Morning Family Series | The CENTER for Performing Arts | $10 |
| All day | Shop activities, treats and offers | Participating village shops | Free |
| 2:30 p.m. | Disney's Frozen, CENTERstage Productions | The CENTER for Performing Arts | $29 |
| 3 to 5 p.m. | Victorian Traditional Carolers | Village shop route, TBA | Free |
| About 5 to 8 p.m. | Tree and menorah lighting, per the event application | Municipal lot near the Doughboy statue | Not listed |
The Frozen run starts Friday, December 4, at 7:30 p.m. and continues through January 17, 2027. Through December 20, shows are Fridays at 7:30 p.m. and weekends at 2:30 p.m., with no performances December 25 through 27. Times for the evening lighting can still change, so check the organizers' latest posting before you head into the village.
The Rest of the Season
Outside December 5, the calendar is spread across the month:
- Wilderstein Historic Site, 330 Morton Road, runs holiday tours Fridays, Saturdays and Sundays from November 27 through December 27. Tours start at noon, 1, 2 and 3 p.m. Tickets are $20 and sold on arrival, and the site is closed Christmas Day.
- The CENTER's Saturday Morning Family Series follows its December 5 show with Mischievous Elf on December 12 at 11 a.m. All seats are $10.
- The 4th Annual Rhinebeck Winter Craft Fair & Market is listed for December 12, 10 a.m. to 3 p.m., at 45 N. Park Road. Entry is $1, and proceeds go to the high school's Classes of 2028, 2029 and 2030.
- The Rhinebeck Farmers Market keeps its outdoor season going every Sunday, 10 a.m. to 2 p.m., through December 27. It uses the same municipal lot where the tree will stand.
On Sunday, December 6, the morning after the lighting, the farmers market sets up again in that same lot.
Jake Garay and the Garay‑Michaud Team follow Rhinebeck's calendar week by week, December 5 included. If your plans for this season involve the village, schedule a consultation and we will tell you what we are seeing on the ground.
