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Holiday Season in and Around Millerton, NY
- millertonbusinessa
- 4 days ago
- 3 min read
The holidays are one of the most magical times to experience Millerton and the Hudson Valley. From twinkling lights and local markets to festive performances and cozy gatherings, there’s something for everyone — whether you love art, music, shopping, or simply savoring the season with friends and family.
Here’s your guide to the best holiday events happening in and around Millerton this year:
Saturday, December 6 (11am–4pm)
Sunday, December 7 (10am–2pm)
The Troutbeck Holiday Bazaar returns with an extraordinary mix of artisans, boutiques, and designers. You’ll find handcrafted jewelry from Mary MacGill, timeless caftans from two, sustainable fashion by Rentrayage, and so much more — plus plenty of fun for little ones and delicious food options.
Members and hotel guests enjoy early access on Saturday from 10–11am.
Location: Troutbeck, Amenia, NY
Admission: Free with RSVP
Saturday, December 13 – Sunday, December 14
Join Stissing House — and Deborah Needleman — for the third annual Craft Feast, a weekend celebrating American craft. Fifty makers and dealers will fill the tavern with handmade pottery, baskets, textiles, and more. Expect broth, brooms, whittled spoons, and carols too — it’s as charming and cozy as it sounds.
Location: Stissing House, Pine Plains, NY
Kids on Stage Presents: A Christmas Carol
Saturday, December 13 at 11am & 2pm
Sunday, December 14 at 11am
This heartwarming musical adaptation of the Dickens classic is performed by young local actors in the Kids on Stage program. Follow Ebenezer Scrooge as he’s visited by ghosts of Christmas Past, Present, and Future — and reminded of the true meaning of the season.
Tickets: $10 per person
Location: The Center for Performing Arts at Rhinebeck
November 14 – December 30
All aboard for a magical journey to the North Pole! The beloved Polar Express experience brings the story to life with hot chocolate, dancing chefs, and a visit from Santa himself. Each child receives a silver sleigh bell — “the first gift of Christmas.”
Location: Westbrook Station, Kingston, NY
Tickets: Adults $47–56 | Children $37–46
November 21 – December 24
Capture the magic with Santa photos at the Poughkeepsie Galleria. Walk-ups are welcome every day until closing, and families who book online get extra perks.
Location: Poughkeepsie Galleria, Poughkeepsie, NY
Saturday, December 13 | Parade starts at 6pm
Lineup begins at 4pm at the Red Hook Firehouse. Expect festive floats, food trucks, plenty of lights, and a grand finale with Santa and Mrs. Claus.
Location: Downtown Red Hook, NY
November 28–January 3 | Wednesdays–Sundays, 4:30–9pm
A Berkshire favorite, Winterlights transforms Naumkeag’s gardens into a wonderland of sparkling light displays, music, and festive treats.
Location: Naumkeag, Stockbridge, MA
November 21–December 30 | 5–8pm (until 8:30pm Saturdays)
Wander through an illuminated forest of over half a million lights at Harvest Moon Farm & Orchard. The glowing trails, holiday music, and family-friendly atmosphere make this a perfect seasonal outing.
Location: Harvest Moon Farm & Orchard, North Salem, NY
November 28–30, December 4–7 & 18–28 | 5–9pm
Drive through hundreds of twinkling light displays set to festive music broadcast right into your car. It’s a classic Hudson Valley holiday tradition that delights kids and adults alike.
Location: Dutchess County Fairgrounds, Rhinebeck, NY
Saturday, December 6 | 7–9:30pm
Test your holiday knowledge with host Alec Sisco at this lively trivia night featuring questions about holiday movies, songs, and traditions. Grab your friends, sip something festive, and join the fun.
Location: The Stissing Center, Pine Plains, NY
Saturday, December 13
Families are invited for a cozy morning featuring a reading of A Christmas Carol, hot chocolate, and a tour of the beautifully decorated Wilderstein mansion.
Location: Wilderstein Historic Site, Rhinebeck, NY
Plan Your Holiday Getaway
Whether you’re shopping local, watching a show, or sipping cocoa under the lights, Millerton and its neighboring towns make the holiday season truly special. Stay tuned to Visit Millerton for more festive happenings, winter dining spots, and ways to make the most of this magical time of year.