Seasonal & Holidays
2025 Brewster Holiday Guide: Lights, Festive Fun & Good Cheer
From small-town charm to seasonal celebrations, these hometown holiday highlights bring the spirit of the season to life.
The holiday season has arrived in Brewster, bringing twinkling lights, cheerful events and plenty of ways to make memories close to home. From light displays to beloved local traditions, here are the hometown holiday highlights you won’t want to miss.
Please note: Dates and details are subject to change, so be sure to check with each organizer before you go — many events require tickets or reservations in advance.
Westchester’s Winter Wonderland Drive-Thru Light Show
When: Select dates through December 31, 2025 | Evenings; timeslots vary by day
Where: Kensico Dam Plaza, Valhalla, NY
Just a short ride from Brewster, this 1.2‑mile drive-through in Valhalla features dazzling tunnels, dancing trees and synchronized holiday music. Guests can see Westchester’s “best Santa” and enjoy themed displays from the comfort of their car. Tickets are required, with peak and off‑peak pricing per vehicle.
More info: wwinterwonderland.com
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Holiday Lights on the Farm
When: Fridays and Saturdays, December 5 – 20, 2025 | 5 PM – 8 PM
Where: Muscoot Farm, 51 NY-100, Katonah, NY
In nearby Katonah, Muscoot Farm's annual event offers a dose of rustic seasonal charm. Visit the animals inside decorated barns, enjoy live music and delicious food and get in the spirit with holiday-themed activities. Holiday Lights on the Farm is held rain or shine; registration is required ($6/person, free for children aged 2 and under).
More info: eventbrite.com/e/holiday-lights-on-the-farm-tickets
Stew Leonard’s 31st Annual Christmas Tree Lighting
When: Thursday, December 4, 2025 | 4:30 PM – 5:30 PM
Where: Stew Leonard’s, 99 Federal Road, Danbury, CT
Just across state lines, this annual event features carolers, dancers, a local school band and Santa arriving by fire truck. Families can enjoy hot cocoa, cookies and face painting while watching the giant tree light up. No tickets are required for this festive kickoff.
More info: stewleonards.com/eventbrite-event/stew-leonards-danbury-31st-annual-christmas-tree-lighting-celebration
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Holiday Ornament Workshop
When: Saturday, December 6, 2025 | 9:00 AM – 10:30 AM
Where: Stew Leonard’s, 99 Federal Road, Danbury, CT
Another Stew Leonard's event, this workshop lets kids and adults craft personalized ornaments while enjoying breakfast snacks and a storytime with Santa. Participants leave with a handmade keepsake to brighten their holiday décor.
More info: stewleonards.com/eventbrite-event/holiday-ornament-workshop/
Winter Wonderland at Pegasus Farm
When: Saturday, December 6, 2025 | 1:00 PM – 6:00 PM
Where: Pegasus Farm, 310 Peach Lake Road, Brewster, NY
This family‑friendly event includes hayrides, horse meet‑and‑greets, visits with Santa and festive food for purchase. Guests can explore the farm while enjoying seasonal cheer and community spirit. Attendees are asked to reserve a timed arrival slot—though you're welcome to stay as long as you like once you arrive!
More info: allevents.in/brewster/winter-wonderland-at-pegasus-farm
The Wynotte Sisters Holiday Concert
When: Saturday, December 6, 2025 | 7:00 PM
Where: Old Town Hall Theater, 67 Main Street, Brewster, NY
This annual concert features whimsical harmonies from The Wynotte Sisters, joined by Ernie Sites and The Monkeytown Milk Spillers. The performance takes place amid community‑decorated trees, creating a cozy, festive atmosphere. Tickets for this festive concert can be purchased online for $25.
More info: culturalartsco.com
Breakfast with Santa & The Grinch
When: Sunday, December 21, 2025 | 10:00 AM & 12:30 PM seatings
Where: Putnam County Golf Course, 187 Hill Street, Mahopac, NY
Less than 15 minutes out from Brewster, families can enjoy a full breakfast buffet while meeting Santa and his mischievous guest, the Grinch. Photo opportunities abound, and the event sells out annually for both seatings, so advance tickets are essential.
More info: putnamcountygolfcourse.com/post/breakfast-with-santa-at-putnam-county-golf-course-on-saturday-december-13th
Enjoy the season, make a few memories close to home and have a happy holiday, Brewster!
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