The Best Things to Do in Westchester & the Hudson Valley This Weekend

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Looking for fun plans this weekend? Whether you’re in Westchester County or exploring the scenic Hudson Valley, there’s no shortage of festive events, cultural experiences, and family-friendly activities. Here’s your ultimate guide to making the most of your weekend.

Westchester Highlights

1. Yonkers Downtown Tree Lighting Ceremony

When: Friday, December 5
Kick off the holiday season at Getty Square in Yonkers with a magical tree lighting, holiday music, hot chocolate, and plenty of photo ops. This free event is perfect for families.
Learn More [mommypoppins.com]


2. Rye Brook Winterfest

When: Friday, December 5
Celebrate winter at Pine Ridge Park with train rides, ice sculptures, a visit from Santa, and festive lights. Free admission makes this a great family outing.
Event Details [mommypoppins.com]


3. Holiday Lights at Muscoot Farm – Katonah

When: Opens Friday, December 5
See Muscoot Farm transformed into a winter wonderland with decorated barns, holiday-themed activities, live music, and food trucks.
More Info [mommypoppins.com]


4. Shake It Off’s Snowflake Ball – Scarsdale

When: Friday, December 5
Dance, craft, and enjoy delicious pizza at this festive winter celebration. Perfect for kids and families.
Event Details [mommypoppins.com]

Hudson Valley Highlights

1. Kingston Snowflake Festival

When: Friday, December 5
Enjoy horse-drawn carriage rides, ice sculpture carvings, flame throwers, and live entertainment in Kingston’s charming downtown. Santa and Mrs. Claus arrive on an antique fire truck!
Learn More [mommypoppins.com]


2. Holiday on the Lake – Carmel

When: Saturday, December 6
Kick off the holiday season with a Christmas Village craft fair, hayrides with Santa, live music, a chowder fest, and two tree lighting ceremonies.
Event Details [hvmag.com]


3. The Nutcracker – Sugar Loaf Performing Arts Center

When: December 5–7
Experience the magic of this holiday classic performed by the Warwick Dance Collective and guest artists.
More Info [hvmag.com]


4. Grand Portfolio Wine Tasting – Millbrook Vineyards

When: Saturday, December 6
Sample a curated selection of wines at one of the Hudson Valley’s most scenic vineyards. Perfect for a festive date or a relaxing afternoon.
Learn More [hvmag.com]


5. Walkway Over the Hudson

Take a scenic stroll across this iconic pedestrian bridge connecting Poughkeepsie and Highland. Enjoy breathtaking views of the Hudson River—especially stunning at sunset.
Plan Your Visit [thetourist…cklist.com]

Pro Tips

  • Dress warmly: Many events are outdoors.
  • Reserve early: Popular activities like wine tastings and performances sell out fast.
  • Bring cash: Some craft fairs and food vendors may not accept cards.

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Picture of Nina Rodriguez

Nina Rodriguez

I'm Nina Rodriguez. I am a Realtor at Coldwell Banker Realty. I live and work in the Hudson Valley and love everything this area has to offer. If you live or thinking about moving here, you have come to the right place! Stay up to date on Events, Outdoors, Real Estate, and more. I’m looking forward to connecting with you soon! See you around town! hello@thehvlife.com | 914.685.8410
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