Poughkeepsie Christmas Events & Things to Do 2025

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...

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.

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...

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...

Discover unique, handcrafted treasures at the annual Holiday Pottery Show & Sale. This anticipated event features over 30 regional ceramic artists, jewelers, and artisans offering a convenient way to shop locally for the holidays. Members can enjoy an exclusive preview and a special discount, while proceeds benefit the artists and...

Step into a winter wonderland at the Merwinsville Hotel's Annual Christmas/Holiday Show. They transform the historic hotel into a festive spectacle, showcasing impressive collections of nutcrackers, Santa Claus figures, and intricate Worlds Fair miniatures. Visitors can browse and purchase unique artwork, holiday crafts, jewelry, and ornaments. The event spans two...

Experience the magic of the holiday season at the 23rd Annual Festival of Trees, Ann's Place's premier fundraising event. Wander through a enchanting forest of uniquely decorated trees, discover treasures in the Boutique and Quilter's Corner gift shops, and try your luck with high-end raffle prizes. This signature event for...

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,...

Get ready for a swinging, rocking holiday celebration with the Rock This Town Orchestra's Christmas Spectacular! This family-friendly show brings the most wonderful time of the year to life with energetic performances of beloved Christmas classics. Expect a full stage production filled with festive cheer, and a special surprise appearance...

Prepare for a genuine New York holiday tradition with Jessica Lynn's "A Very Merry Classic Christmas." This acclaimed show, celebrated as a top holiday event, offers a dazzling multi-media spectacle featuring dancers, marching bands, and choirs. Sing along to beloved Christmas carols and become part of an immersive experience that...

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.

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...

Step into a world of enchantment at Lumina, an illuminated forest experience at Harvest Moon Farm & Orchard. Wander through pathways adorned with over half a million brilliant lights, creating a magical glow perfect for all ages. Enjoy captivating light shows synchronized to music, discover new photo opportunities, and savor...

Join the festivities for New Year's Eve at The Silk Factory. This event promises a memorable way to welcome the new year with a special celebration.

Bring the little ones to Savannah's for a magical Brunch with Santa! This beloved annual event invites Santa Claus to spread holiday cheer, listen to Christmas wishes, and pose for photos with children. It's a delightful experience designed to create lasting memories for families.

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...

Step into a festive holiday atmosphere at Devitt's Nursery & Supply for their 'Christmas on the Farm with Eggbert' event. This unique tradition brings back the beloved Eggbert for a memorable experience. Visitors can capture fun photos and explore the nursery's seasonal decorations, making it a charming stop during the...

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....

Get into the holiday spirit at the Annual Christmas Parade! This cherished community event brings together decorated floats, marching bands, and local organizations for a festive procession. It's a wonderful opportunity to experience the joy and excitement of the season with friends and family.

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...

Join the New Fairfield community for their annual Holiday Lights Parade, a cherished tradition that illuminates the town with festive cheer. Witness a dazzling procession of creatively decorated floats and vehicles, all aglow with vibrant holiday lights, bringing the magic of the season to life.