From 6 p.m. on Friday, December 4, to 6:30 p.m. on Saturday, December 5, Rye Brook has two tree lightings, in two parks, run by two different governments. The Village of Rye Brook holds Winterfest at Pine Ridge Park on Friday night. The Town of Rye holds Holiday Lights at Crawford Park on Saturday afternoon. Most of the community holiday season happens in that one stretch.
The Village's 2026 Fall Brochure lists six fall special events. For December it lists one. So Friday night carries the Village's whole December, and Saturday's event at Crawford Park is the other half of the weekend. The library programs, cooking classes and shop events this month all fall before or after those two days.
Six fall events, then one in December
Rye Brook Recreation had a full fall. The brochure lists Back to School Movie in the Park, Pumpkin Patch, a Food Truck Festival, Howloween, Trunk or Treat and Pumpkin Smash. Then it says the Winterfest event is "coming in December" to "commence the holiday season." The Village lists no Turkey Trot, December craft night or separate menorah event. Both lightings happen at Winterfest.
Here's what the Village has posted for Winterfest:
- When: Friday, December 4, 6:00 to 9:00 p.m.
- Where: Pine Ridge Park, 17 Mohegan Lane
- Who: All residents
- What: A Christmas tree and menorah lighting, a special guest from the North Pole, ice sculptures carved on site, train rides and vendors
The event runs three hours after dark. You can arrive after work, and the ice carving and train rides keep going through the evening. Winterfest is a Friday night in a neighborhood park, which makes it the more local of the two events.
The coat drive closes the same day
Winterfest isn't the only thing on December 4. The Paula's Pals 16th Annual Coat Drive has been collecting clean, reusable coats since September 25, and its last day is December 4, 2026.
The collection boxes are not at Pine Ridge Park. They are at two Village buildings:
- Rye Brook Recreation Office, 938 King Street
- Rye Brook Posillipo Center, 32 Garibaldi Place
If you've been meaning to give away a coat your kids have outgrown, drop it at King Street or Garibaldi Place before Friday evening. You won't find a box at the lighting.
Saturday moves to Crawford Park, run by the Town
Less than 24 hours after Winterfest ends, the Town of Rye holds its own event. Holiday Lights at Crawford Park runs Saturday, December 5, from 3:30 to 6:30 p.m., with the tree lit at 5:00 p.m. The Town calls it "our most anticipated community event of the year." It promises selfies with Santa, holiday food and snacks, crafts and live holiday music, and it's free. The Town announced the event on October 10.
The two events differ in a few ways. Saturday starts in daylight and has one fixed moment, the 5:00 p.m. lighting. Friday is all after dark and spread across three hours. The Town says local volunteers and sponsors "turn Crawford Park into a dreamy Holiday Village every year." Winterfest is put on by the Village's own Recreation department.
To drive in, take North Ridge Street to the Crawford Park driveway, where cars park by the mansion. The Village's brochure gives these same directions for Rye Hills Park, a Village park that sits behind the wall at Crawford Park.
| Winterfest | Holiday Lights at Crawford Park | |
|---|---|---|
| Run by | Village of Rye Brook | Town of Rye |
| Day | Friday, December 4 | Saturday, December 5 |
| Hours | 6:00 to 9:00 p.m. | 3:30 to 6:30 p.m. |
| Lighting | Christmas tree and menorah | Tree lighting at 5:00 p.m. |
| Headline extras | Ice carving, train rides, North Pole guest, vendors | Santa selfies, food, crafts, live music |
| Location | Pine Ridge Park, 17 Mohegan Lane | Crawford Park, off North Ridge Street |
Families who want both can do it without missing either lighting. You'd spend Friday evening at Pine Ridge and get to Crawford Park by about 4:30 on Saturday for the 5:00 lighting.
The weeks before the weekend
Several smaller events lead up to December 4.
Thursday, November 19. The Wine Cellar Rye Ridge at 122 South Ridge Street holds a free Thanksgiving wine sampling from 5:00 to 6:30 p.m. You must be 21 or older to sample or buy. The organizer says walk-ins are welcome if the online sign-up sells out. The event listing has the details. Also at Rye Ridge, the shopping center's directory lists Taichi Bubble Tea as "Opening Soon."
Friday, November 20. Fiddleheads Cooking Studio runs a family cooking class for all ages at Crawford Park from 6:00 to 7:30 p.m. The Crawford Park class page links to registration.
Tuesday, December 1. The Port Chester-Rye Brook Public Library continues its free Art Comes Alive lecture series with "The Drama of Caravaggio," 1:30 to 2:30 p.m. Retired art educator Paul Zaccagnino gives the talks. Space may be limited, so register at the library or call 914-939-6710 ext. 103.
The weeks after
After December 5, the calendar gets lighter and moves indoors.
Tuesday, December 8. The library's Create and Design a Gingerbread House is at 6:00 p.m. for teens and adults. Houses are built from paper, colorful shapes and stickers, so there's no baking. Registration is required, either in person or at (914) 939-6710 ext. 103.
Monday, December 14. Karaoke & Mocktails at the Library starts at 6:00 p.m. It's the second of the library's two fall karaoke nights, and registration is required here too.
Saturday, December 19. Fiddleheads holds the last family cooking class on its fall and winter schedule at Crawford Park, from 10:00 to 11:30 a.m. It's the last date on the Fiddleheads fall and winter list.
The Crawford Park concerts start again January 31
The Town has announced its 2027 Winter Concert Series, with three Sunday afternoon concerts by the Westchester Philharmonic at 2 p.m.:
- January 31, a program of music for strings and winds
- March 14, the Influencers Piano Trio
- May 2, The Art of the String Quartet
The January 31 concert is at 2 p.m. on a Sunday, about eight weeks after the Saturday lighting at Crawford Park.
If someone at Pine Ridge or Crawford Park asks what your house would sell for, Andrew Rogovic grew up in Rye Brook and can give you a real answer. Request a Free Home Valuation before the holidays, and you'll have the number in hand when January arrives.
