Woodstock Christmas Events & Things to Do 2025

Experience the magic of the Hudson Valley Hullabaloo Holiday Market, a premier destination for unique, locally-made gifts. Discover over 75 curated vendors offering everything from artisanal crafts to designer goods. Enjoy festive food, live entertainment, and special attractions like tintype portraits and permanent jewelry. It's the perfect place to find...

Experience the festive spirit at the Reformed Church of New Paltz Christmas Fair. Discover a delightful array of handmade crafts, unique gifts, and seasonal decorations. Enjoy delicious festive food and warm beverages while soaking in the holiday cheer. It's the perfect place to find special treasures and get into the...

Discover or create the perfect gift at this family-friendly community event. Guests can handcraft beautiful items from natural materials, browse unique crafts by local artisans, and enjoy live entertainment including a puppet show and music. Festive food and warm beverages are also available.

Discover the 53rd Annual DCCF Holiday Craft Fair, a premier artisan festival in Poughkeepsie, NY. This event showcases over 100 juried artists and makers, offering a unique shopping experience filled with handmade art, crafts, and specialty goods. It's an ideal alternative to Black Friday, focusing on the connection between visitors...

Experience the festive spirit at the Dutchess Handmade Holiday Pop-Up Shop, a vibrant showcase of original, locally crafted art. Discover unique gifts and decorations from over 70 talented regional artists, all gathered in Arts Mid-Hudson's gallery. It's the perfect destination to find one-of-a-kind treasures and support local creativity during the...

Experience the charm of a traditional German Weihnachtsmarkt at Germania of Poughkeepsie's Christkindlmarkt. This festive event offers a delightful array of authentic German food, holiday treats, and specialty gifts from local vendors. Enjoy the cozy atmosphere with indoor dining and a heated market tent, perfect for kicking off the holiday...

Embark on a magical journey at The Wonderland of Lights, a spectacular drive-through holiday light show at the Dutchess County Fairgrounds. Immerse yourself in hundreds of dazzling displays, from captivating tunnels to larger-than-life illuminated sculptures, all designed to ignite your holiday spirit. Enhance the experience with optional 3D elf glasses...

Discover A Frosty Fest, the Hudson Valley's premier holiday lights spectacular. This event offers a captivating drive-thru experience filled with dazzling lights, animations, and music, all enjoyed from the comfort of your vehicle. Meet beloved characters like Santa, Mr. & Mrs. Frosty, and Rudolph, and enjoy magical comedy shows.

Experience the magic of the holiday season at the Windham Christmas Festival! This cherished community event features a dazzling light parade, festive caroling, and the heartwarming presence of Santa Claus. Join them for a tree lighting ceremony that illuminates the town square, creating a truly enchanting atmosphere for all to...

Catskill Ballet Theatre presents their 40th-anniversary production of The Nutcracker, a cherished holiday tradition in the Hudson Valley. Audiences will be enchanted by the timeless story, magical sets, and stunning choreography as they follow young Clara's adventures. Witness a battle against an evil Queen Mouse, journey through a winter wonderland,...

Experience the magic of Woodstock's Christmas Eve on the Green, a cherished tradition for over 90 years. The Village Green transforms into a festive wonderland with a beautifully lit Christmas tree. Caroling begins at 5:00 PM, followed by Santa's exciting arrival at 5:30 PM, where he'll hand out stockings to...

Embark on a magical journey aboard THE POLAR EXPRESS™ Train Ride, inspired by the classic story. Passengers will relive the tale as they travel to the North Pole, enjoying hot chocolate and cookies served by dancing chefs. The Conductor will punch golden tickets, and characters will lead caroling and entertainment....

Experience the enchanting Sinterklaas Festival Day in Rhinebeck, a unique Dutch tradition celebrating children as royalty. Immerse yourself in a day filled with creative workshops, captivating performances by over 350 artists, and a magical Children's Starlight Parade. This community-powered event transforms the village into a wonderland of music, dance, and...