December in Dutchess County brings in a season of warmth, sparkle, holiday charm, and festive celebrations.
From Rhinebeck’s luminous winter displays and Poughkeepsie’s curated craft markets to intimate Millbrook workshops and warm gatherings throughout Dutchess County, here is your guide to the month’s most holiday-inspired events.
Kevin McCurdy’s Holiday Spirit Festival
Open now through December 27
Bowdoin Park, Wappingers Falls
Celebrate 21 years of holiday magic at Kevin McCurdy’s Holiday Spirit Festival! Enjoy dazzling light displays, festive tunnels, and nostalgic fun blended with creativity and technology for an unforgettable family experience.
holidayspiritfestival.com
The Wonderland of Lights: Drive-Thru Light Show
December 4-7, 18-28
Dutchess County Fairgrounds, Rhinebeck
Experience holiday magic from the comfort of your car! Drive through dazzling light displays synchronized to festive music for a sparkling, joy-filled experience the whole family will love.
thewonderlandoflights.com
‘Winter Glow:’ Holiday Drive-Thru Experience
December 4-7, 11-14, 18-28
Heritage Financial Park, Wappingers Falls
Drive through Winter Glow, a magical mile-long adventure that brings the holidays to life. Larger-than-life light displays sparkle all around you, filling the night with festive wonder. As you drive through this glowing world, every moment is designed to ignite joy and holiday spirit.
winterglowexperience.com
Pawling Concert Series: Alias Brass
Friday, December 5
All Saints’ Chapel, Trinity-Pawling School, Pawling
Get into the holiday spirit with Alias Brass at All Saints Chapel! Enjoy masterful performances blending classical, jazz, and pop from trumpet, French horn, trombone, and tuba in a festive concert experience.
pawlingconcertseries.org
Millbrook Parade of Lights
Friday, December 5
Main Street, Millbrook
Enjoy the Millbrook Fire Department’s annual lights parade tradition, and a visit from Santa Clause himself! Main Street in Millbrook is illuminated with twinkling displays and lights, while emergency vehicles, fire trucks, and festive floats cruise by and bring holiday cheer.
villageofmillbrookny.com
Sinterklaas Day and Dutch Holiday Traditions
Saturday, December 6
Wappingers Historical Society, Wappingers Falls
Experience the story of Sinterklaas through hands-on activities, traditional Dutch treats, and holiday cheer! Families will love this festive, educational celebration featuring a surprise visit from St. Nicholas.
wappingershistoricalsociety.org
Piggy Bank Bazaar
Saturday, December 6
New Hackensack Reformed Church, Wappingers Falls
Holiday fun for little shoppers! December 6, kids explore six rooms of handmade gifts under $3, enjoy free wrapping, photos, and treats, all guided by our helpful volunteers at New Hackensack Church.
nhrc-church.org
Holiday Trivia Night
Saturday, December 6
Stissing Center for Arts & Culture, Pine Plains
Put your holiday knowledge to the test! Alec Sisco hosts a fun-filled Trivia Night at Stissing Center, packed with movies, TV, traditions, and festive competition.
thestissingcenter.org
Branchwater Farms Holiday Craft Fair
Saturday, December 6
Branchwater Farms, Milan
Celebrate the season at Branchwater Farms’ 4th annual holiday craft fair! Shop for handmade gifts such as jewelry, candles, ceramics, and textiles. Grab some specialty food and beverage items, and enjoy hot dogs from Overlook Farms!
branchwaterfarms.com
Opening Reception – This Must Be The Place
Saturday, December 6
Maxon Mills, Wassaic Project, Wassaic
Join the Wassaic Project for the opening reception of their 2026-2026 Winter Exhibition, This Must Be The Place, featuring works by artists such as Meli Bandera, Danny Dobrow, Stepahnie Santana, Deborah Simon, and more.
wassaicproject.org
Troutbeck Holiday Bazaar
December 6 – 7
Troutbeck, Amenia
Shop local artisans, boutique designers, and unique gifts at Troutbeck’s Holiday Bazaar! Enjoy outdoor fun, kids’ activities, and a festive gift-wrapping station. Shop dozens of vendors offering homeware, jewelry, clothing, furniture, and toys – find the perfect gift for your loved ones this holiday season!
troutbeck.com
Doodle Auction and Cocktail Party
Sunday, December 7
Stissing Center for Arts & Culture, Pine Plains
Celebrate the season with festive doodles, music, and holiday treats! Bid on unique creations by local and celebrity artists, all benefiting Stissing Center’s arts and community programs.
thestissingcenter.org
Holiday Open House
Sunday, December 7
The Elmendorph Inn, Red Hook
The Elmendorph Inn shines in its holiday finest as Historic Red Hook welcomes you to enjoy live seasonal music, hot mulled cider, homemade cookies, and fresh-baked beehive oven treats. Free and open to all—no registration required.
historicredhook.org
Churchtown Dairy Holiday Market
Sunday, December 7
Churchtown Dairy, Hudson
Browse all sorts of goodies at Churchtown’s festive holiday market – the perfect place to pick up gifts for this holiday season, or something for yourself! Enjoy wagon rides, goat walks, and shop wreaths, pottery, jewelry, and more!
churchtowndairy.org
Wassaic Holiday Stroll
December 6-7 + 13-14
Wassaic Project, Wassaic
Celebrate the season at the Wassaic Project’s Holiday Market! Discover unique, handmade creations by local makers and artist alumni – from playful art kits to one-of-a-kind gifts and creative holiday essentials.
wassaicproject.org
Cookbook Club Gathering
Monday, December 8
Hudson Valley Brewery, Beacon
Join local food preserver Rebecca Echevarria for a community cookbook club featuring dishes from Samin Nosrat. Bring a dish to share and enjoy great company at Hudson Valley Brewery; RSVP to participate.
More info + RSVP here!
Gift of Warmth Cookie Swap and Food Drive
Thursday, December 11
Branchwater Farms, Red Hook
Join Slow Food Hudson Valley at Branchwater Farms for their second annual Gift of Warmth event! Share homemade cookies, donate food, and enjoy hearty gumbo, cider, and community on a festive afternoon.
branchwaterfarms.com
The Nutcracker at Wethersfield + Q&A
Thursday, December 11
The Moviehouse, Millerton
A behind-the-scenes film following choreographer Troy Schumacher as he reimagines The Nutcracker at a magical Hudson Valley estate, uniting dancers and audience in an immersive holiday experience.
themoviehouse.net
Gingerbread House Decorating Party
Friday, December 12
Turletes Building at the Town Park, Millbrook
Get in the holiday spirit at the Town of Washington’s Annual Gingerbread House Decorating Party, an event that the whole family can enjoy. Gingerbread house and icing will be provided, bring your own candy to create your very own unique and festive masterpiece!
washingtonny.myrec.com
Children’s Holiday Storytime
Saturday, December 13
Wilderstein Historic Site, Rhinebeck
Experience the magic of the holidays at Wilderstein! Delight in a reading of A Christmas Carol, enjoy hot chocolate and treats, then wander through the mansion’s sparkling seasonal decorations.
wilderstein.org
Windborne: The Music of Midwinter
Saturday, December 13
Stissing Center for Arts & Culture, Pine Plains
Windborne brings radiant harmonies and festive instrumentation to a special midwinter performance celebrating winter traditions across cultures. Enjoy luminous vocals, intimate arrangements, and a warm seasonal atmosphere.
thestissingcenter.org
Holiday Shop Crawl + Carolers
Saturday. December 13
Village of Rhinebeck
Shop for holiday gifts, enjoy live carolers, and soak in the festive atmosphere. Walk through the Village of Rhinebeck and explore holiday pop-up shops, then stop by the Beekman Arms for a festive fireside finale.
instagram.com/rhinebeckchamber/
Holiday Cookie Decorating at Troutbeck
Saturday, December 20
Troutbeck, Amenia
A sweet holiday celebration for families! Decorate fresh cookies with Chef Emma Isakoff, enjoy holiday music, and share fun, festive moments with cookie kits provided for all ages.
troutbeck.com
Christmas Eve Dinner at Troutbeck
Wednesday, December 24
Troutbeck, Amenia
Troutbeck invites you to a Christmas Eve dinner with a seasonal à la carte menu, featuring special seafood dishes alongside poultry, meats, and vegetarian options.
troutbeck.com
Free Day at Dia Beacon
Sunday, December 28
Dia Beacon, Beacon
Hudson Valley residents enjoy free admission to Dia Beacon on the last Sunday of each month. Explore extraordinary contemporary art, including Andy Warhol’s striking 102-canvas work, Shadows, and other long-term exhibitions.
diaart.org
New Year’s Eve Party in Amenia
Wednesday, December 31
Isabela’s, Amenia
Enjoy an a la carte menu of specialties, drinks, and music at Isabela’s New Year’s Eve dinner celebration! Stick around for a complimentary midnight champagne toast & late night snacks.
instagram.com/isabela_amenia