As winter settles over Westchester and the Hudson Valley, the region bursts with cultural experiences, outdoor adventures, family-friendly activities, and enriching events for all ages. Whether you’re planning a fun outing with kids, seeking an engaging experience for seniors, or looking for concerts, workshops, and entertainment for young adults, this week offers plenty to explore. Here are some of the top happenings from January 16 to January 22.
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Friday, January 16
- 2026 Vision Board Workshop – Thornwood, NY
- After School Childcare Programs – YMCA of Greenwich (nearby)
- JAM-uary at The Ashokan Center – Olivebridge, NY (all weekend)
- Book on the Hudson Fair – The Wire, Coxsackie, NY (all weekend)
- Hike + Learn: Learn to Snowshoe – Catskills Visitor Center, Mt. Tremper, NY
- Key of Q: “It’s About Time!” – Howland Cultural Center, Beacon, NY
- The Librarians Documentary – Tinker Street Cinema, Woodstock, NY
- Mommy & Me: Animals & Nature, Westmoreland Sanctuary, Mt. Kisco
Saturday, January 17
- Homeschool Month – LEGOLAND Discovery Center Westchester, Yonkers, NY
- Glenview Holiday Tour – Hudson River Museum, Yonkers, NY
- Curtain Call Winter Dramatic Arts Classes – Stamford, CT (nearby)
- Aquila Theatre: The Hound of the Baskervilles – Tannersville, NY (also Jan 18)
- New Paltz Repair Café – New Paltz, NY
- UlsterCorps 17th Annual Celebration of Service – Rosendale Recreation Center, Rosendale, NY
- Lucky’s Winter Extravaganza Sports Memorabilia Show – Westchester County Center, White Plains, NY (also Jan 17–18)
- Conigliaro Consort, Jazz on Main, Mount Kisco NY
Sunday, January 18
- Winter Aqueduct Walk – Hudson River Museum, Yonkers, NY
- Aquila Theatre: The Hound of the Baskervilles – Tannersville, NY
- Book on the Hudson Fair – The Wire, Coxsackie, NY (final day)
- Lucky’s Winter Extravaganza Sports Memorabilia Show – White Plains, NY
- Frozen Waterfalls Hike + Bonfire + Mulled Wine – Awosting Falls Area (Departing Poughkeepsie)
- Duotone Landscape Painting Workshop, The Hendrick Hudson Free Library, Verplanck, NY
Monday, January 19
- MLK Day Family Robot Building Class, Harbor Island Park, Mamaroneck, NY
- Colonial Candle Dipping Workshop, Westmoreland Sanctuary, Mount Kisco, NY
Tuesday, January 20
No specific events listed for this date at this time check back later for updates
Wednesday, January 21
No specific events listed for this date at this time check back later for updates
Thursday, January 22
- Out There Film Series: Jimpa – Jacob Burns Film Center, Pleasantville, NY
- Hank Azaria & the EZ Street Band: Springsteen Celebration – Paramount Hudson Valley Theater, Peekskill, NY (listed as Jan 23, but the series includes events leading up to this date)
- Mahjong Ladies Night! Divino Speakeasy, Hastings On Hudson, NY
- Lorenzo Simoni Spontaneous Trio, Jazz on Main, Mount Kisco, NY
- Gold Dust Woman: Music of Stevie Nicks & Fleetwood Mac, Capitol Theatre, Port Chester
- Classic Tour at Yankee Stadium, Bronx
- Everyday Rebellions: Collection Conversations, Brooklyn Museum
- WCA Annual Business Breakfast, New York Athletic Club – Pelham Manor
- Ramy Youssef Live, The Bell House, Brooklyn
- Lettuce – Cook World Tour, Wellmont Theater, Montclair, NJ (nearby)
- Shane Gillis Live, Madison Square Garden, NYC
Whether you’re exploring with kids, spending quality time with older loved ones, or heading out solo for entertainment and cultural enrichment, Westchester and the Hudson Valley offer something fresh and exciting this week. From hands-on workshops and historic tours to concerts, film screenings, and serene nature experiences, the region continues to shine even in the heart of winter. Bundle up, get out there, and make the most of January’s vibrant offerings!
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