Here’s a blog-style roundup of the best events happening in Westchester and the Hudson Valley for the weekend of November 14–16, 2025:
Top Events in Westchester County
🎄 Holiday Kickoff at Cross County Center (Yonkers)
- Tree Lighting Ceremony: Friday, Nov 14
- Pop-Up Ice Skating Rink & Santa Photos: All weekend
- Holiday Food Truck Market: Saturday & Sunday
Start the festive season with lights, skating, and delicious bites at one of Westchester’s most popular holiday hubs. [westcheste…dabout.com]
🎭 Taconic Opera Presents Puccini’s Turandot
- Where: Tarrytown Music Hall
- When: Saturday & Sunday, Nov 15–16
Opera lovers can enjoy Puccini’s masterpiece in an intimate setting. [americantowns.com]
🎨 Ossining Arts Council Small Works Holiday Sale
- Where: Ossining
- When: Saturday, Nov 15
Shop unique, locally made art pieces—perfect for early holiday gifts. [americantowns.com]
🎃 The Great Jack-O’-Lantern Blaze (Croton-on-Hudson)
- When: Through Nov 16
Thousands of hand-carved pumpkins illuminate Van Cortlandt Manor in this iconic Hudson Valley spectacle. [suburbanju…egroup.com]
Top Events in the Hudson Valley
📚 Women’s Reading Retreat (Windham)
- When: Nov 14–16
A cozy, book-centered weekend for those craving connection and reflection. [insideando…tateny.com]
🎶 Live Music Highlights
- Trombone Shorty & Orleans Avenue at UPAC (Kingston) – Friday, Nov 14
- Sonny Landreth & Cindy Cashdollar at Levon Helm Studios (Woodstock) – Friday, Nov 14
Both promise unforgettable performances blending jazz, blues, and roots. [insideando…tateny.com]
🛍️ Holiday Bazaar at The Tin Barn (Germantown)
- When: Nov 15–16
Local makers, live music, food trucks, and festive drinks make this a must-visit holiday market. [insideando…tateny.com]
🍂 Harvest Market at Wylder Windham
- When: Nov 15–16
Enjoy curated vendors, live music, and cozy Catskills vibes with fire pits and gourmet pop-ups. [hvmag.com]
🚂 Catskill Mountain Railroad Polar Express (Kingston)
- When: Starts Nov 14
A magical train ride inspired by the classic holiday story—perfect for families. [hvmag.com]
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