Nestled in the picturesque Litchfield Hills, Woodbury, Connecticut, is a charming New England town that beautifully combines rich history, vibrant culture, and scenic landscapes. With its quaint streets, antique shops, and friendly community, Woodbury offers a perfect blend of relaxation and excitement for both residents and visitors alike. As 2025 approaches, the town's event calendar promises an array of activities that showcase its unique character and allow visitors to immerse themselves in the local culture. Whether you’re looking to enjoy the arts, embrace the seasons, or support local businesses, Woodbury has something for everyone. Here’s a guide to the top Woodbury, CT events in 2025.
1. Woodbury Winterfest: A Fun-Filled Winter Celebration
One of the first events to mark the year is Woodbury Winterfest, typically held in January. This beloved winter festival draws crowds with its chilly charm and festive spirit. The highlight of Winterfest is the Ice Sculpture Competition, where talented artists create stunning, intricate ice sculptures that shimmer in the cold New England air. This event transforms the town into a frosty wonderland, perfect for families and anyone looking to enjoy the beauty of winter.
In addition to the ice sculptures, Winterfest features a host of family-friendly activities, including ice skating, horse-drawn sleigh rides, and games for kids. Food trucks serve up hot drinks and seasonal treats like hot chocolate, roasted chestnuts, and freshly baked cookies. The combination of art, nature, and community makes Winterfest a must-attend event for anyone visiting Woodbury in January.
2. Woodbury Spring Garden Tour: A Glimpse into the Town’s Natural Beauty
As the snow melts and flowers begin to bloom, the Spring Garden Tour brings out the best of Woodbury’s outdoor beauty. Held every May, this self-guided tour gives visitors the chance to explore some of the most beautiful private gardens in the area. The tour showcases a variety of garden styles, from classic English gardens to modern landscaping designs.
For garden enthusiasts, the Spring Garden Tour is an opportunity to gain new insights and ideas for their own outdoor spaces. Visitors will enjoy strolling through lush flower beds, manicured lawns, and gardens filled with vibrant colors. It’s also a great event to meet local gardeners, who often share tips on sustainable gardening and growing specific plants. The event is typically a fundraiser for local causes, making it an opportunity to give back to the community while enjoying the best of nature.
3. Woodbury Summer Concert Series: Live Music in a Scenic Setting
In the warmer months, Woodbury comes alive with the sounds of the Summer Concert Series, a popular event that runs from June through August. Held in various outdoor venues around town, these free concerts feature an array of musical genres, including rock, jazz, folk, and classical. The concerts are designed to bring the community together and are often set in scenic locations such as parks and open-air venues.
Whether you’re attending with friends, family, or a special someone, the Summer Concert Series provides a relaxed atmosphere to enjoy great music while soaking up the beauty of the surrounding landscape. Many of the concerts feature local food vendors, offering everything from fresh seafood to creative vegetarian options, so you can enjoy a meal while you listen. It’s a wonderful way to spend a summer evening in Woodbury, enjoying both the music and the company of the community.
4. Woodbury Farmers Market: Fresh, Local, and Delicious
If you’re in Woodbury during the spring, summer, or fall, the Woodbury Farmers Market is an essential stop. Held every Saturday from May through November, the market brings together local farmers, artisans, and food producers to showcase the best of the region’s seasonal offerings. Visitors can find everything from fresh fruits and vegetables to locally made cheeses, artisanal breads, and homemade jams.
The market also features live entertainment, cooking demonstrations, and occasional special events. It’s an excellent place to support small local businesses while filling your basket with fresh, organic ingredients for the week. Whether you’re looking to pick up ingredients for dinner or just want to enjoy the lively atmosphere, the Woodbury Farmers Market is a must-visit event.
5. Woodbury Harvest Festival: A Fall Tradition for All Ages
When autumn arrives, Woodbury’s Harvest Festival brings the town together for a celebration of all things fall. This event, typically held in October, is a family-friendly extravaganza with a wide range of activities, including pumpkin carving contests, hayrides, and a corn maze. The festival also features a petting zoo, giving children the chance to interact with farm animals, and live music that sets a festive tone.
One of the event’s most anticipated attractions is the apple pie contest, where locals and visitors alike compete for the coveted title of best apple pie in town. The festival also includes food vendors selling delicious seasonal treats, such as cider donuts, roasted corn, and caramel apples. If you’re looking for a fun, festive way to embrace the fall season in New England, Woodbury’s Harvest Festival is the place to be.
6. Woodbury Holiday Village Stroll: A Magical Holiday Tradition
As the year draws to a close, the Holiday Village Stroll ushers in the holiday season with twinkling lights, festive decorations, and the spirit of giving. Held each December, this event invites visitors to stroll through the town’s historic district, which is beautifully decorated for the holidays. Shops and restaurants along the route offer special discounts and promotions, giving you the perfect opportunity to do some holiday shopping while enjoying the town’s festive atmosphere.
The tree lighting ceremony is a highlight of the event, where the central Christmas tree is illuminated in a dazzling display of lights. Visitors can also enjoy caroling performances, visits with Santa Claus, and other holiday-themed activities. The Holiday Village Stroll is a great way to experience the magic of the season while supporting local businesses and artists.
7. Woodbury Classic Car Show: A Showcase of Automotive Excellence
For car enthusiasts, the Woodbury Classic Car Show is a standout event. Held annually in the summer, this car show brings together vintage and classic car owners who display their prized vehicles for the public to admire. Whether you’re a long-time collector or simply enjoy the beauty of well-maintained classic cars, this event is a must-see.
The Classic Car Show also features live music, food trucks, and plenty of opportunities to meet fellow car lovers. It’s a perfect day out for families, as there are activities for everyone—whether you’re admiring the cars, sampling delicious food, or taking part in a fun raffle. This event is an exciting way to spend a summer day in Woodbury.
8. Woodbury Art Walk: Discover Local Creativity
Woodbury is home to a thriving arts community, and the Woodbury Art Walk is the perfect way to discover local talent. This event typically takes place in the warmer months, when local galleries and artists open their doors to the public for a day of exploration and creativity. The Art Walk features a variety of artistic styles, from painting and photography to sculpture and mixed media.
Visitors can enjoy browsing the galleries, speaking with the artists, and learning more about their creative processes. The Art Walk also includes interactive activities, allowing visitors to engage with the art in unique and meaningful ways. If you appreciate art or simply want to explore the creative side of Woodbury, the Art Walk is an event you won’t want to miss.
9. Woodbury Turkey Trot: A Thanksgiving Tradition
The Woodbury Turkey Trot is a beloved event that takes place on Thanksgiving Day, offering participants the chance to get active before indulging in the holiday feast. This 5K run/walk is a family-friendly event that attracts both serious runners and those just looking for a fun way to start the holiday. The event is also a fundraiser, with proceeds benefiting local charities, making it a great way to give back to the community during the holiday season.
Participants often dress in festive costumes, and the atmosphere is filled with excitement and holiday cheer. The Turkey Trot is a perfect way to stay active, connect with the local community, and start Thanksgiving with a sense of accomplishment.
Conclusion: Experience the Best of Woodbury, CT in 2025
Woodbury, Connecticut, offers a wealth of events throughout the year that highlight the town’s charm, community spirit, and natural beauty. From the winter magic of Winterfest to the festive cheer of the Holiday Village Stroll, there’s always something happening in this quaint New England town. Whether you’re an art lover, a foodie, or someone who enjoys spending time outdoors, Woodbury, CT events promise to provide memorable experiences for all.
As you plan your visit to Woodbury in 2025, be sure to add these incredible events to your calendar. Whether you're exploring the fall colors at the Harvest Festival or enjoying the music at the Summer Concert Series, you’re sure to find an event that captures the essence of this delightful town.