With tens-of-thousands of lights and classic charm, Woodstock makes a great winter destination! Here’s how you can spend your visit:
- Holiday Lights & Festivals: Start your holiday experience with the Lighting of the Square on the Friday after Thanksgiving. The historic Woodstock Square is illuminated with thousands of twinkling lights and offers plenty of photo ops, carolers, and food trucks. You’ll also find free horse-drawn carriage rides on select weekends in December, which offer a charming way to view the lights and historic buildings.
- Shopping & Local Events: Woodstock has a vibrant lineup of holiday markets and shopping experiences. Shop small with the town’s amazing shops! The popular Ladies Night Out event also gives shoppers an evening of festive fun, complete with snacks, drinks, and holiday deals across shops around the Square.
- Festive Activities for Kids and Families: The town hosts a variety of family-friendly events, including the Christmas Parade and Cookies & Churros with Santa.. Children will enjoy meeting Santa at the Santa Hut on the Square, while families can explore the Legend of the Pickle Scavenger Hunt for a fun, quirky holiday adventure.
- Opera House Shows and Music: For a dose of the arts, the historic Woodstock Opera House presents seasonal shows like White Christmas, The Nutcracker, and holiday concerts. Enjoy live music events, theater productions, and holiday movie screenings that are perfect for cozy winter outings.
- Dining & Cozy Spots: After exploring, warm up with a meal at one of Woodstock’s local restaurants. Explore unique dining options and local shops, providing a blend of historic ambiance and local flavors.
- New Year & Groundhog Day Celebrations: Woodstock extends its winter festivities into the New Year, highlighted by the annual Groundhog Day Festival in early February. This event celebrates the town’s connection to the classic movie Groundhog Day, which was filmed in Woodstock.