The Hudson Valley shines brightest during the season of holiday events. Twinkling lights, festive markets, and timeless traditions make every corner special. We love sharing the magic of this time with you. When planning your getaway to Caldwell House, you’ll find warmth, cheer, and moments worth remembering.
Many of our guests ask what makes this region so magical in winter. Every town embraces the season differently, after all. That said, there’s plenty to see, do, and experience. We can’t wait to share the finest season in the Hudson Valley.
Holiday Events with Sparkling Lights
The Hudson Valley lights up in December with unforgettable holiday events. Every display feels bigger, brighter, and more joyful than the last. You’ll find two favorite attractions that locals and guests love to return to yearly.
Peace, Love & Lights at Bethel Woods
📅 Nov 28 — Dec 28: 5–10pm, Daily
Bethel Woods comes alive with an immersive drive‑through light show that feels magical. Wind through dazzling tunnels and glowing arches.
Even the themed displays brighten the night sky. Families love the mix of music and lights; couples call it unforgettable. Bring hot cocoa and enjoy every glowing moment.
Wonderland of Lights at Dutchess County Fairgrounds
📅 Nov 28–30: 5–9pm
📅 Dec 4–7: 5–9pm
📅 Dec 11–14: 5–9pm
📅 Dec 18–28: 5–9pm
The Dutchess County Fairgrounds is magnificent this time of year. It transforms into a glowing wonderland. But don’t take our word for it. Drive past shimmering displays, giant ornaments, and festive arches. Each brightens the night, making even the stars a little jealous.
The experience is playful and bright. So, naturally, it’s a favorite for couples and families. Bring loved ones, roll down the windows, and let those lights amaze you.
Family-Friendly Holiday Events in Hudson Valley
Families love the Hudson Valley holiday events each year. Attractions welcome kids and adults with festive spirit, laughter, and plenty of small-town charm. If you’re looking for the perfect getaway from the city, this is it!
These celebrations offer something special for everyone. Think magical train rides, bustling markets, and scenic winery trails.
Polar Express Train Ride on Catskill Mountain Railroad
📅 Nov 14 – Dec 30: Times Vary
Step aboard the Polar Express Train Ride and relive the magic of Chris Van Allsburg’s classic story. The Catskill Mountain Railroad brings the tale to life with carols, hot chocolate, and a trip to the “North Pole.” The highlight comes when Santa boards and gifts each guest a silver sleigh bell as a keepsake.
Hudson Valley Hullaballoo Holiday Market
📅 Nov 22: 10am – 5pm
📅 Nov 23: 10am – 4pm
The Hudson Valley Hullaballoo Holiday Market feels festive, creative, and energetic. Local makers, artists, and crafters fill the space with one‑of‑a‑kind gifts. You’ll find handmade jewelry, unique prints, and fun holiday décor.
Shoppers love the mix of tradition and whimsy, and families enjoy the cheerful vibe. This market is the perfect stop when you want memorable holiday gifts and community spirit.
Holiday Fineries at the Wineries
📅 Nov 22–23: 11am – 5pm
📅 Dec 6 & 7: 11am – 5pm
📅 Dec 13 & 14: 11am – 5pm
Holiday Fineries at the Wineries blends festive fun with local wine country charm. Each winery greets you with tastings as you travel along the Shawangunk Wine Trail. Seasonal décor and a warm welcome add to the charm. Guests collect handmade ornaments at every stop. The experience is leisurely, social, and full of cheer.
Holiday Events on Stage & Screen
Hudson Valley stages light up during holiday events, bringing music, theater, and tradition to life. Guests enjoy seasonal shows that make the holidays more enchanting. You’ll return with plenty of stories to share about your experiences.
West Point Holiday Show
📅 Dec 6 & 7: 2pm
The West Point Holiday Show is a tradition that combines military precision with a festive spirit. The U.S. Army Band and Cadet Glee Club perform holiday favorites. Families and visitors love the combination of pageantry, music, and community pride at West Point. The show takes place in early December at Eisenhower Hall. It’s the perfect festive kickoff to the season.
A Christmas Carol with Master Storyteller Jonathan Kruk
📅 Dates and Times Vary
Jonathan Kruk’s A Christmas Carol performance is unlike any other. His storytelling style brings Dickens’ classic tale to life with voices, gestures, and heartfelt energy. Guests are drawn into the story, laughing at Scrooge’s stubbornness and tearing up at his redemption.
The intimate setting makes the event more personal. It’s as though the story is being told just for you. It’s a Hudson Valley holiday tradition worth experiencing at least once.
More Holiday Fun Around Hudson Valley
The Hudson Valley brims with even more holiday events beyond lights and shows. Guests enjoy cozy meals, local culture, and unique shopping for a more memorable visit.
Storm King Art Center draws visitors with striking outdoor art against a winter backdrop. Local breweries pour seasonal favorites that warm chilly nights. If you haven’t tried Hudson Valley’s craft beer, you’re in for a treat! Our best restaurants are bursting with flavor, too! They’ll welcome you with hearty menus and festive décor.
Everywhere you go, you’ll find experiences that round out your holiday getaway. So get ready for the festive fun to begin.
Plan Your Hudson Valley Holiday Vacation
Your holiday getaway deserves a setting that feels both festive and personal. The Hudson Valley offers it all: lights, markets, shows, and cozy corners that welcome you in. Planning now means you won’t miss a moment of the season’s best holiday events.
We’d love to host your stay at Caldwell House. After a day of festive fun, return to warmth, comfort, and a room that feels like home. Book your room today and let us help you transform this holiday season into lasting memories.
Photo Credit: © Studio France with AI via canva.com, © JillWellington from pixabay via canva.com, © Shutter2U via canva.com
