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25 Things to Do in Dutchess County This Winter
December 2, 2025
  1. Go sledding at Bowdoin Park in Wappingers Falls; glide down some of the best sledding hills in the area. 
  2. Ice skate at McCann Ice Arena in Poughkeepsie, take one of their open skating sessions to boost your skills and to stay active this winter.
  3. Cruise through Rhinebeck’s Wonderland of Lights drive-thru show, a perfect pre-holiday activity for all ages! 
  4. Take in stunning snowy views and hike, bike, snowshoe, or x-country ski at one of these beautiful Hudson Valley nature spots:
    1. Fishkill Ridge Trail
    2. Bear Mountain State Park
    3. Bannerman Castle
  5. Discover the perfect cup of hot cocoa at one of these cozy cafes:
    1. Samuel’s Sweets Shop in Rhinebeck 
    2. Taste Budd’s Chocolate & Coffee Cafe in Red Hook
    3. Babbette’s Kitchen in Millbrook 
    4. The Crafted Kup in Poughkeepsie
  6. Attend a local parade of lights! A classic winter tradition among the small towns of Dutchess County. 
  7. Shop local! The towns of Millbrook, Amenia, Millerton, Poughkeepsie, and Rhinebeck are perfect for small town strolling and shopping. Check out some of our favorite boutiques!
    1. J.McLaughlin 
    2. Juniper Collective 
    3. Westerlind
    4. Freddy B
    5. Workers & Dreamers
  8. Visit The Moviehouse in Millerton for a movie, or specialty film screening. 
  9. What could beat gushing over adorable animals at a local zoo? Visit red pandas, lemurs, lynxes, and more at the Trevor-Lovejoy Zoo located on the Millbrook School campus. Don’t forget to make a reservation online beforehand at millbrook.org/plan-your-visit/hours–admission. 
  10. Visit House of Stefas, an all-new elevated dining experience in Millbrook. Taste authentic freestyle Greek recipes while feeling as though you’ve been transported to a different Mediterranean-like dimension. 
  11. Get cozy inside and settle in with a good book to read. Explore great selections at Oblong Books in Millerton, Merritt Bookstore + Toystore in Millbrook, or Stanza Books in Beacon. 
  12. Sometimes there’s nothing sweeter than grabbing a delicious baked treat from a local bakery…
    1. Vitsky Bakery in Wassaic 
    2. Silo Bakery in Amenia 
    3. Kelly’s Bakery in Poughkeepsie 
    4. Bread Alone Bakery & Cafe in Rhinebeck 
  13. Stop by the Stissing Center in Pine Plains for some live music, art shows, and meaningful performances this winter season.
  14. For a low-key evening dining out, here are some casual restaurants to visit:
    1. Four Brothers Restaurant in Amenia, Millerton, Dover, Pleasant Valley, 
    2. Willa in Millerton
    3. Il Figlio Enoteca in Fishkill
    4. The Wild Kitchen & Bar in Beacon  
    5. Mill House Brewing Company in Poughkeepsie 
  15. Stay active! Bike, jog, or unwind on a leisurely stroll down the Harlem Valley Rail Trail, a scenic 26 mile trail that spans from Wassaic to the outskirts of Hillsdale. 
  16.  Fight the cold this winter and stay warm at a local winery or distillery. Here are our top picks:
    1. Millbrook Vineyards & Winery in Millbrook 
    2. Tenmile Distillery in Wassaic 
    3. Taconic Distillery in Stanfordville 
  17.  Take a farm tour at Elk Ravine Farm in Amenia, and enjoy a hands-on interaction with their friendly, fluffy Scottish Highland calves. 
  18.  Find unique, pre-loved treasures at one of our favorite antique shops:
    1. Millbrook Antiques Center
    2. Hunter Bee
    3. Millerton Antiques Center 
    4. Montage Antiques 
    5. Hyde Park Antiques Center
  19.  Explore the hiking trails at the Dover Stone Church Preserve. This forever-protected 174-acre public preserve, located in the Village of Dover Plains, features more than four miles of hiking trails leading to a natural rock formation called the Dover Stone Church. 
  20.  Explore unique works at all the art galleries the area has to offer:
    1. Belvoir Gallery
    2. Fine Home Source
    3. The Re Institute
    4. Geary
    5. Blueberry Hill Galleries
    6. Albert Shahinian Fine Art/Upstairs Galleries
    7. Studio 44
    8. Mad Rose Gallery
    9. Dia Beacon
    10. Betsy Jacaruso Studio and Gallery
    11. Frances Lehman Loeb Art Center
  21. Go sporting clay shooting at Orvis Sandanona in Millbrook. If you’ve never shot sporting clays, sign up for a lesson before going out on the course!
  22. Visit one of these gorgeous decorated historic sites for the holiday season!
    1. Staatsburgh State Historic Site in Staatsburgh
    2. Mills Mansion in Staatsburgh
    3. Wilderstein Historic Site in Rhinebeck
    4. Mesier Homestead in Wappingers Falls
    5. Clermont State Historic Site in Germantown
    6. Locust Grove Historic Site in Poughkeepsie
    7. Vanderbilt Mansion in Hyde Park
  23.  Tour the Eleanor Roosevelt National Historic Site, home of the nation’s first Presidential Library, and over a thousand acres of gardens and trails. 
  24. Indulge in nostalgia at Happy Valley Arcade Bar in Beacon, where they have 30 classic arcade games, pinball machines, and live music.
  25. Discover all the hidden gems of Rhinebeck through an interactive Scavenger Hunt that takes you all throughout the most historic and picturesque parts of town.