If you’re looking for festive fun in Westchester and the Hudson Valley between December 19th and 25th, you’re in for a treat. As someone who loves exploring every nook of our beautiful region, I’ve rounded up the best events happening this holiday week. From sparkling light shows to cozy concerts and family-friendly activities, there’s something magical waiting for you every single day. Let’s make this holiday season unforgettable—right here at home!
Table of Contents
Friday, Dec 19
- 17th Annual Greenwich Reindeer Festival & Santa’s Workshop (Westchester): Mon–Fri 12–6 pm; Sat 9 am–6 pm; Christmas Eve 9 am–3 pm
- Cross County Center Pop‑Up Holiday Ice Skating & Market (Yonkers): daily during mall hours
- Lumina Magical Light Experience Harvest Moon Farm & Orchard, North Salem (Fri–Sun evenings)
- Newburgh Frost Fest (HV): Lantern walks, hot cocoa, ornament-making, Santa fun run (Dec 19–21)
- Holiday Drinks & Trivia at Angry Orchard (Walden): 6–8 pm trivia and cider night
- Holiday Comedy & Speed Dating (East Fishkill): 6:30–9 pm at Sloop Brewing Co
- Greenwich Reindeer Festival & Santa’s Workshop
437 North Street, Greenwich, CT - Christmas in America (Holiday Experience) 30 Warren Place, Mount Vernon, NY 10550 – Fri Dec 19, Santa 3–7 pm
- Holiday Train Show — Greenburgh Nature Center, Scarsdale (weekend)
- Westchester Children’s Museum “Bricktacular” — Rye (weekend)
- LEGOLAND Discovery Center Holiday Bricktacular — Yonkers (weekend)
Saturday, Dec 20
- Holiday Vendor Market (Yonkers): 11 am–7 pm
- Expressive Kids Art (2–3 yrs) at Katonah Art Center
- Candlelight: Christmas Carols on Strings (Mt. Kisco): 6 & 8:30 pm showings
- Victorian Christmas at Sunnyside (HV): 10 am–3 pm tours & crafts
- Olana Winter Solstice Celebration (Hudson): 1–5 pm activities & donkey visits
Saugerties Solstice Lantern Walk at Opus 40: 3–7 pm - Kwanzaa Celebration at Hudson Hall: 3–5 pm family arts & drumming
- Josimar y Su Yambú – Latin Music Concert — Westchester County Center, White Plains (Sat, Dec 20, 8 pm)
- Expressive Tot Art Class (Katonah Art Center) 40 Radio Circle Dr, Mt. Kisco, NY 10549
- 914 PopUps Holiday Vendor Market 8000 Mall Walk, Yonkers, NY 10704 – Sat, 11 am–7 pm
- Lumina Magical Light Experience Harvest Moon Farm & Orchard, North Salem (Fri–Sun evenings)
- Holiday Train Show — Greenburgh Nature Center, Scarsdale (weekend)
- Westchester Children’s Museum “Bricktacular” — Rye (weekend)
- LEGOLAND Discovery Center Holiday Bricktacular — Yonkers (weekend)
Sunday, Dec 21
- Teen Art Night (Hartsdale): ages 5–12
- Mommy & Me Animals & Nature (Mt. Kisco)
- Bronx Zoo Holiday Lights (nearby): through Dec 21
- Winter Solstice Activities at Olana (Hudson)
- Mid‑Hudson Discovery Museum 3D Snowman (Poughkeepsie): 1 pm hands-on fun
- Westchester Children’s Museum “Bricktacular” 100 Playland Parkway, Rye, NY 10580
- Holiday Train Show at Greenburgh Nature Center 99 Dromore Rd, Scarsdale, NY 10583
- Lumina Magical Light Experience Harvest Moon Farm & Orchard, North Salem (Fri–Sun evenings)
- Holiday Train Show — Greenburgh Nature Center, Scarsdale (weekend)
- Westchester Children’s Museum “Bricktacular” — Rye (weekend)
- LEGOLAND Discovery Center Holiday Bricktacular — Yonkers (weekend)
Monday, Dec 22
- Classic Tour at Yankee Stadium (Bronx): evening tours
- Jonas Brothers Concert (Barclays, NYC): 7:30 pm
- Christmas Spectacular Starring The Rockettes (Radio City): 4 pm show
Tuesday, Dec 23
- Radio City Christmas Spectacular: 11 am performance
- Grand Holiday Illumination at Untermyer Gardens (Yonkers)
- Holiday Twilight Tours at Boscobel House & Gardens
- Lyndhurst Mansion Holiday Tours
635 S Broadway, Tarrytown, NY 10591 - Westchester’s Winter Wonderland Drive‑Thru 1 Bronx River Parkway, Valhalla, NY 10595
Wednsday, Dec 24
- Final Candlelight Carols on Strings – Mt. Kisco
- Winter Wonderland Drive‑Thru – Valhalla
- Radio City Christmas Spectacular: 5 pm show
- Grand Kyiv Ballet – The Nutcracker (NYC): 12 pm matinee
- Moulin Rouge! The Musical (NYC): 8 pm performance
Thursday, Dec 25
- Westchester’s Winter Wonderland Drive‑Thru – Valhalla
- Radio City Christmas Spectacular: 11 am matinee
- New York Knicks vs Cleveland Cavaliers (MSG): 12 pm game
There you have it—seven days packed with holiday cheer across Westchester and the Hudson Valley! Whether you’re sipping cocoa under twinkling lights, enjoying live music by candlelight, or joining a festive market, these events are the perfect way to celebrate the season. So grab your loved ones, bundle up, and dive into the magic. Wishing you joy, laughter, and plenty of holiday memories—see you out there!
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