With spirits soaring and holiday cheer all around, December truly is an enchanting time of year in New York’s Hudson Valley. Here in Dutchess County, there are plenty of attractions that will warm your heart and brighten your day.
Many Dutchess County historic sites will be all decked out for special holiday tours and festive events. If you’re searching for unique, handmade gifts for your family and friends, grab your holiday shopping list and head straight to one of Dutchess County’s many holiday craft fairs. Be sure to check out our list of Holiday Festivals and Lights Displays in Dutchess, and stay tuned for details on our Top 20 Places to Ring in 2026!
Here’s a look at some more can’t-miss Dutchess experiences in December. Get your camera ready! And if you’d like to share your pictures, click here or tag @DestinationDutchess on social media.
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Friday, Dec. 5, 8:30 p.m., at Living Water Church, Poughkeepsie
Experience the timeless music of The Beatles like never before. The Highline String Quartet presents a tribute to the music of The Beatles performed under the gentle glow of candlelight in this unique, multi-sensory musical performance. Hear all your Beatles favorites, like "Here Comes the Sun," "I Want to Hold Your Hand," "Eleanor Rigby" and "Penny Lane." Click here to reserve tickets.
Friday, Dec. 5, 6–7 p.m., at Oblong Books, Rhinebeck
Oblong Books hosts an author event and book signing with James Beard Award-winning author Tamar Adler in conversation with Lacey Schwartz Delgado. Adler will talk about her new book, "Feast on Your Life," which is a record of daily delights from inside the kitchen and just outside it. It's designed to help you see the magic in everyday meals and embrace the art of cooking with a renewed sense of peace, helping you find greater happiness and mindfulness the kitchen. Adler is the award-winning author of "An Everlasting Meal;" "Something Old, Something New;" and the bestselling "The Everlasting Meal Cookbook. "She is a contributing editor at Vogue and has been a New York Times Magazine columnist. Click here to complete the required registration for this free event.
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Saturday, Dec. 6, 12–3 p.m., at Happy Valley Arcade Bar, Beacon
Bring your four-legged friends to Happy Valley Arcade Bar’s outdoor courtyard to pose for pictures with Santa Claus! Inside Happy Valley, you’ll find more than two dozen fully operational vintage video game consoles — including Pac-Man, Asteroids, Centipede and Donkey Kong— along with several vintage pinball machines and a well-stocked bar featuring a full assortment of beer, wine and spirits.
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Saturday, Dec. 6, 4 p.m. at Rhinebeck High School
Guest conductor William Stevens leads the Northern Dutchess Symphony Orchestra in its "Sounds of the Season" holiday concert. Local voice-over actor Jason Dempsey will narrate Charles Dickens' timeless tale, "A Christmas Carol," accompanied by the orchestra performing familiar carols and original music. Click here to purchase tickets, and be sure to check out other concerts on the NDSO’s 2025-26 schedule, which picks up after the new year and continues through the spring.
Saturday, Dec. 6, 3–5 p.m., at Maxon Mills, Wassaic
The Wassaic Project presents the opening of its winter art exhibition, titled "This Must Be The Place,” in its Maxon Mills gallery. Maxon Mills is an historic, seven-story wooden grain elevator along the train tracks that has been repurposed into a uniquely magnificent venue for contemporary artists of all types to show their work. “This Must Be The Place” features the work of 11 artists and will be on display through March 14. Click here to learn about the featured artists. While you’re in Wassaic, be sure to walk across the street to The Lantern for a delicious meal and a beverage or two.
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Multiple dates at Kaatsbaan Cultural Park, Tivoli
Kaatsbaan presents two fun and unique productions which are guaranteed to bring you joy this holiday season. All performances will take place in the Black Box Theater on Kaatsbaan's scenic 153-acre campus on the Hudson River.
• Everett Bradley's "Holidelic" (Friday, Dec. 12, and Saturday, Dec. 13, 8 p.m.) — Immerse yourself in a world where funk meets Christmas joy with Grammy-nominated performer and percussionist Everett Bradley’s "Holidelic," a sensational holiday funk revue that will electrify your senses. Bradley, known for his work with Bruce Springsteen and Bon Jovi, takes on the role of Papadelic, Funk’s Father Christmas, an amalgamation of George Clinton and Santa Claus.
• "Nut/Cracked" (Friday, Dec. 19, and Saturday, Dec. 20, 7 p.m.; Sunday, Dec. 21, 2 p.m.) — Choreographer David Parker and The Bang Group present their version of "The Nutcracker," which offers a playful, witty rendition of Pyotr Ilyich Tchaikovsky’s iconic work. Featuring a blend of dance styles that includes ballet, tap and disco, "Nut/Cracked" combines humor and artistry to create a delightfully unique production.
Friday and Saturday, Dec. 12 and 13, at Eastdale Village, Poughkeepsie
Head to Eastdale Village — Poughkeepsie's trendy live-work-play community — for a two-day shopping, dining and entertainment extravaganza! Participating establishments will offer perks and incentives so you can finish (or start) your holiday shopping, enjoy a tasty meal and treat yourself to a fun night out and about. Every purchase you make earns you a raffle ticket for a chance to win prizes worth hundreds of dollars. There will be a Hot Cocoa Crawl starting at The Crafted Kup on Friday from 6–8 p.m. Pose for photos with Santa on Cottage Square on Saturday from 4–6 p.m. Click here for complete details and a list of participating businesses.
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Saturday, Dec. 13, 2 p.m. and 7:30 p.m., and Sunday, Dec. 14, 3 p.m., at the Bardavon 1869 Opera House, Poughkeepsie
The New Paltz Ballet Theatre returns for its 29th season to present this classic holiday production at the historic Bardavon, The Oldest Continuously Operating Theater in New York State. Come along with Marie as she dreams of a fierce battle between giant mice and toy soldiers followed by a magical journey through the Land of Snow to the Kingdom of Sweets. Click here to purchase tickets.
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Sunday, Dec. 14, 4 p.m., at Curry Estate, Hopewell Junction
Step back in time to Victorian England and dine with the Cratchit family and beloved Tiny Tim at this dinner theater performance of Charles Dickens' heartwarming holiday classic, "A Christmas Carol." Enjoy an evening of laughter, nostalgia and holiday cheer the whole family will cherish. Settle in for a delicious three-course dinner with your choice of entree and enjoy the show. Click here to reserve tickets. If you'd like to experience all the charm and elegance of a European inn, be sure to book a room and spend the night at this 1863 Georgian Colonial Estate, which features 16 spacious, recently renovated rooms with luxury linens and all the modern conveniences.
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Tuesday, Dec. 24, 5–9 p.m., at Terrapin, Rhinebeck
Treat yourself to the best of farm-to-table cuisine in an elegant setting at Terrapin in the Village of Rhinebeck. Chef Josh Kroner's special prix fixe Christmas Eve menu offers a diverse assortment of entrees featuring local and organic ingredients, including multiple vegetarian, vegan and wheat-free options. Click here to see the menu and book your reservations.
Terrapin is ADA compliant and offers handicapped parking, an access ramp that leads directly into the main dining room, and an accessible, gender-neutral bathroom. Terrapin is also a member of the the Village of Rhinebeck Autism Supportive Community, which works to make the community more welcoming for people on the autism spectrum and with other disabilities. Chef Kroner is an active committee member, and Terrapin has sensory kits available and offers reduced noise in the dining space at designated times of day.
It’s never too early to start planning your summer excursions, and several of Dutchess County’s most popular summer attractions are already gearing up for next season. Tickets are available for these events and would make wonderful holiday gifts:
• Hudson Valley Renegades (Wappingers Falls) — The Renegades minor-league baseball team celebrated their 31st season in 2025 and their fifth season as the High-A affiliate of the New York Yankees in the South Atlantic League. The Renegades play 66 home games each season at Heritage Financial Park (formerly Dutchess Stadium). Current Yankees who sharpened their skills with the Renegades include Anthony Volpe and Jasson Dominguez. Full-season and half-season ticket packages are available for the 2026 season, and their team store is stocked with all sorts of great merch.
• SplashDown Beach (Fishkill) — “America’s Biggest Little Water Park” features water slides and attractions for all ages. Get your pulse racing on the Humunga Half-Pipe (New York’s only zero-gravity half-pipe) or The Megalodon raft ride. Relax and cool off as you float down the Croc Creek Wavy Lazy River in your own tube. The Pelican Bay Water Playground has four new water slides and a 500-gallon dumping bucket. Discounted season passes for 2026 are available.
• Bannerman Castle (Beacon) — The ruins of this Scottish-style castle on Pollepel Island in the Hudson River are truly a sight to behold. Built by military surplus dealer Frank Bannerman in the early 1900s, the castle, the adjacent residence and the surrounding gardens are all being painstakingly restored by the Bannerman Castle Trust. Special events like musical and theatrical performances, movie nights, lectures and themed dinner events are popular attractions on the island, which is easily reachable aboard the Estuary Steward tour boat or your own kayak or canoe. Stay tuned for ticket information for the 2026 cruise and walking tours of the island, which pick up again in April.
• Old Rhinebeck Aerodrome (Red Hook) — Hold onto your hats for this thrilling experience high above the Hudson River! Schedule a flight in an authentic 1929 open-cockpit biplane and look down from above upon the many scenic wonders of the Hudson Valley. The half-hour Lighthouse Tour offers breathtaking views of Hudson River lighthouses (including the Saugerties Light, the Rondout Light, and the Esopus Meadows Light) and Gilded Age mansions, along with all the natural beauty of the river and the surrounding Taconic, Berkshire and Catskill mountains. You'll want to keep your camera handy for this! Shorter biplane rides are also available. Flights run from May through October, and you can purchase gift certificates for next year now.
• Omega Institute for Holistic Studies (Rhinebeck) — This unique educational retreat center offers workshops, professional training, and rest and rejuvenation retreats. Book your reservation for select 2026 retreats now.
