As winter settles over the Hudson Valley, the region comes alive with cozy seasonal celebrations, live entertainment, creative workshops, and outdoor adventures. Whether you’re planning family fun, meaningful activities for seniors, or vibrant nights out for young adults, Westchester, Rockland, and the Hudson Valley offer something for everyone this week.
Below is your guide to the best happenings.
Table of Contents
Friday, January 23
- Hank Azaria & The EZ Street Band – Springsteen Celebration Peekskill, NY
- Chris D’Elia – Stand‑Up ComedyWest Nyack Levity Live, West Nyack, NY
- Country Night – Line Dancing & Music
Locust Grove Brewing Co., Milton - Film Screening: “Marty Supreme”
Time & Space Limited, Hudson – 7:30 PM - Urban Stomp: Dreams & Defiance on the Dance Floor (Exhibition)
Museum of the City of New York – 10 AM–5 PM - Westchester Knicks vs. Windy City Bulls
Westchester County Center, White Plains - Chris D’Elia Comedy Performance
West Nyack Levity Live - Bear Mountain Ice Rink (Open All Day)
Tomkins Cove - Bird Feeder Watch Fridays
Greenwich Audubon Center - Skeeter Creek Acoustic Duo – Live Music Gray Willow, Earlton
- Mommy & Me: Animals & Nature (Family Activity)Westmoreland Sanctuary, Mount Kisco
- Playtime Storytime (Kids 4 & under)Haverstraw King’s Daughters Public Library – Main Branch (accessible to Westchester families)
- 2026 Discover Boating New York Boat ShowThe Javits Center
- Winter Wonderland at Dogwood Acres Family FarmDogwood Acres Farm, Orange County
- Holiday Lights in Bloom Orange County Arboretum
- LEGOLAND® New York Holiday BricktacularLEGOLAND New York Resort, Goshen
- Holiday Train Show at Arts on the Lake
Saturday, January 24
- Hudson Valley Wedding Market (Day 1)
Makers Central, Tarrytown – 10 AM–5 PM - LOVE A Little More Ski Weekend (Day 1)
Hunter Mountain - Youth Ice Fishing Derby
Wittenberg Sportsmen’s Club, Woodstock – 8 AM–1 PM - Woodstock Farm Festival
Woodstock Community Center – 10 AM–1 PM - Wildflorus: Shawangunk II Photography Exhibition (Open)
Gardiner Library - Family Art Project: Teeny Tiny Things to See
Wave Hill, Bronx – 10 AM–1 PM - Family Science Workshop: Visualizing Heat
Hudson River Museum, Yonkers – 12 PM–4 PM - Children’s Author Visit – Joyce Markovics
Ossining Public Library – 11 AM–12 PM - Bear Mountain Ice Rink (Open All Day)
Tomkins Cove - Frostival at Shake It Off (Ages 3–12)
Shake It Off, Scarsdale - Smile Bright with Rye Smiles (Kids Event)
Westchester Children’s Museum, Rye - Family Art Workshop: Cinematic Wearables
Hudson River Museum, Yonkers - Family Science Workshop: Visualizing Heat
Hudson River Museum, Yonkers - Children’s Author Visit: Joyce Markovics (Ages 5–12)
Ossining Public Library - Family Art Project (Local to Westchester Families at Wave Hill)
Bronx (commonly attended by Westchester residents) - Auditions for The Cottage by Sandy RustinOld Town Hall Theater, 67 Main Street, Brewster, NY – 1:00 PM
- Holiday Lights in BloomOrange County Arboretum
- LEGOLAND® New York Holiday BricktacularLEGOLAND New York Resort, Goshen
- Holiday Train Show at Arts on the Lake
- Kintsugi Class (Gentle Craft Activity) The ReStore, Kingston — Jan 24, 11 AM–1 PM
- Woodstock Farm Festival (Easygoing Indoor/Outdoor Market) Woodstock Community Center — Jan 24, 10 AM–1 PM
Sunday, January 25
- Hudson Valley Wedding Market (Day 2)
Makers Central, Tarrytown – 10 AM–5 PM - LOVE A Little More Ski Weekend (Day 2)
Hunter Mountain - Bear Mountain Ice Rink
Tomkins Cove - Holiday Lights in BloomOrange County Arboretum
- LEGOLAND® New York Holiday BricktacularLEGOLAND New York Resort, Goshen
Monday, January 26
(No major January 26–specific events cited in sources; exhibitions remain open.)
- Wildflorus: Shawangunk II Photography Exhibition (Open)
Gardiner Library - Within the Spiral – Art Exhibit
Highland Falls Public Library - Auditions for The Cottage by Sandy Rustin Old Town Hall Theater, 67 Main Street, Brewster, NY – 7:00 PM
Tuesday, January 27
(No date‑specific events found; ongoing exhibitions continue.)
- Experiment Wildly – Art Exhibit
Unitarian Universalist Congregation, Rock Tavern
Wednesday, January 28
- Winter Wonderland at Dogwood Acres Family Farm (Still Active)
Orange County - Holiday Lights in Bloom
Orange County Arboretum – Evening Hours
Thursday, January 29
- NYC & Westchester Holiday Lights Helicopter Tour
Departs from Westchester County Airport – 4:00 PM–8:30 PM - Whole Farm Climate Adaptation & Mitigation Series (Part of multi‑date workshop)
CCE Ulster Office, Kingston - Exhibits Still Open:
- Wildflorus: Shawangunk II – Gardiner Library
- Experiment Wildly – Rock Tavern
- Within the Spiral – Highland Falls
From lively festivals and live music to relaxing art exhibitions and family science programs, the Hudson Valley, Westchester, and Rockland counties offer a diverse lineup of winter events this week. Whether you’re planning a snowy adventure, a cozy cultural outing, or an evening of entertainment, these communities have everything you need to enjoy the season. Bundle up, explore, and make unforgettable memories between January 23 and January 29—winter fun awaits!
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