25 Things to Do in Dutchess County This Winter
Celebrate winter in Dutchess County with snowy scenic trails, holiday events, cozy eateries, and activities perfect for families, couples, and solo adventurers alike.
On Our Radar - Rhinebeck
Faces, places, treasures, and trends that caught our attention.
December Events in Dutchess County
Discover the warmest and most festive events in Dutchess County happening in December, featuring glittering holiday lights, craft markets, creative workshops, and fun community gatherings that capture the charm and seasonal spirit of the area!
Parades of Lights
Holiday “parades of lights” bring small towns together, blending festive fun with appreciation for volunteer firefighters and EMTs, whose teamwork and mutual aid keep communities safe year-round.
Wilderstein Celebrates an Old-Fashioned Christmas
Wilderstein’s Holiday House offers a nostalgic escape into Victorian-era charm, with festive room designs, family programs, and guided tours that celebrate simple traditions and the estate’s historic beauty.
Helping Hands; Nonprofit Organizations in Dutchess County
Explore Dutchess County’s nonprofit landscape, highlighting diverse organizations, their charitable missions, and how locals can participate, volunteer, or contribute.
Williams Lumber; Rhinebeck
Williams Lumber in Rhinebeck surprises visitors with a festive holiday train display, blending nostalgic charm, family-run business history, and owner Kimberly Williams’ mission to inspire joy.
Chefridi Jewels in Rhinebeck
Adel Chefridi’s Rhinebeck studio showcases Tunisian-inspired, handcrafted jewelry and modern styling advice that encourages everyday wear, mixed metals, expressive pieces, and redefining timeless classics.
Winter at Beekman Arms
The Beekman Arms Inn, operating since 1766, remains Rhinebeck’s cherished gathering place, blending historic charm, community traditions, and visits from both townspeople and prominent guests.
November Events in Dutchess County
November in Dutchess County is bursting with festive energy! From cozy markets to holiday light shows, family activities, and craft fairs, discover this month's most seasonal gatherings and make every weekend a memorable one.
Halloween Events in Dutchess County 2025
Enjoy Dutchess Halloween activities; pumpkin picking, haunted mills, trunk-or-treats, and harvest festivals to get you in the spooky spirit!
October Events in Dutchess County
Experience the magic of October in the Hudson Valley: show jumping, film nights, harvest festivals, ghost tours, and cozy fall traditions await. Get in the autumnal spirit by participating in one of these fall events!
Little Goat Rhinebeck: Mediterranean Flavors & Timeless Charm
Little Goat Rhinebeck blends Mediterranean flavors, local sourcing, and vintage charm in an inviting cafe, bakery, and pantry.
All Things Woolly, at the Rhinebeck Fairgrounds
Discover the New York State Sheep & Wool Festival in Rhinebeck with workshops, vendors, contests, animals, family fun, and fiber arts.
The Beekman Arms & Delamater Inn
Visit Beekman Arms Inn in Rhinebeck, America’s oldest inn, offering historic charm, American cuisine, and centuries of unforgettable stories.
C Cassis: Currant-Based Aperitif Crafted in Rhinebeck
C Cassis in Rhinebeck produces a vibrant currant aperitif using local ingredients, with a charming on-site tasting room.
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