Nestled in the rolling hills of Litchfield County, Woodbury, Connecticut, is a charming town that exudes classic New England appeal. Known for its historic homes, antique shops, and stunning natural beauty, Woodbury is a year-round destination for visitors seeking both relaxation and excitement. From seasonal festivals to outdoor activities, Woodbury offers a diverse range of events that cater to all interests. Whether you're a local or a visitor, the events in Woodbury, CT in 2025 promise something special for everyone. In this article, we explore the top events you won’t want to miss this year.
1. Woodbury Winterfest: Celebrate the Season with Ice and Cheer
Kicking off the year, Woodbury Winterfest is a beloved annual tradition that celebrates the joys of winter. Held in January, the festival transforms the town center into a snowy wonderland, complete with ice sculptures, winter sports, and a festive atmosphere. One of the highlights of Winterfest is the Ice Sculpture Competition, where talented ice artists create intricate, frozen masterpieces right before your eyes. The competition is a sight to behold and offers a unique opportunity to appreciate the artistry of ice.
For families, Winterfest offers an array of activities, including horse-drawn sleigh rides, ice skating, and games for children. Visitors can also warm up with hot chocolate, cider, and delicious seasonal treats from food vendors. Winterfest in Woodbury provides the perfect setting for a fun, winter-themed outing, making it an ideal event to kick off the year.
2. Woodbury Spring Garden Tour: Explore the Blooming Beauty of the Town
As the cold winter months give way to the warmth of spring, the Woodbury Spring Garden Tour showcases the vibrant beauty of the town’s gardens. Typically held in May, this self-guided tour invites visitors to explore the lush, blooming gardens of some of Woodbury’s most beautiful homes and public spaces. Whether you’re a gardening enthusiast or simply enjoy spending time in nature, the tour offers a chance to admire a wide variety of plants and landscaping styles.
The Spring Garden Tour is more than just an opportunity to view beautiful gardens—it’s also a chance to learn about sustainable gardening practices and gain inspiration for your own outdoor spaces. Local garden owners often share their expertise, offering gardening tips and advice. With its breathtaking scenery and educational opportunities, the Spring Garden Tour is a must-visit event for nature lovers in Woodbury.
3. Woodbury Summer Concert Series: Music in the Open Air
When summer rolls around, Woodbury’s Summer Concert Series is one of the most anticipated events in town. Held from June through August, these outdoor concerts offer a diverse lineup of live music, from jazz and blues to folk and rock. Set against the backdrop of the town’s picturesque parks, the concerts provide the perfect opportunity to relax, enjoy great music, and connect with the local community.
The concerts are free and family-friendly, often featuring food trucks and vendors offering delicious local fare. Whether you’re enjoying a picnic with friends or dancing along to your favorite tunes, the Summer Concert Series is a great way to spend a summer evening in Woodbury. The laid-back, welcoming atmosphere and the beautiful setting make these concerts a favorite event for both locals and visitors.
4. Woodbury Farmers Market: Fresh Produce and Local Goods
For a true taste of Woodbury, the Woodbury Farmers Market is an event that should be on your radar. Held on Saturdays from May through November, the market is a vibrant gathering spot for local farmers, artisans, and food vendors. Visitors can find a wide variety of fresh, seasonal produce, handmade crafts, gourmet cheeses, freshly baked bread, and more.
The market is also an excellent opportunity to connect with the community and learn about the importance of supporting local businesses. In addition to fresh food and goods, the market often features cooking demonstrations, live music, and family-friendly activities. Whether you’re stocking up on ingredients for the week or simply enjoying a leisurely stroll through the market, the Woodbury Farmers Market is a great way to experience the local flavor.
5. Woodbury Harvest Festival: A Fall Celebration of Food, Fun, and Family
As the leaves change color and the crisp autumn air arrives, Woodbury’s Harvest Festival celebrates the best of fall. Typically held in October, the festival features an array of fun, family-friendly activities, including pumpkin carving contests, hayrides, and a corn maze. Children can enjoy a petting zoo, face painting, and other interactive activities, while adults can browse vendor booths offering handmade goods, fall decorations, and seasonal treats.
One of the highlights of the Harvest Festival is the apple pie contest, where locals compete to make the best pie in town. With its lively atmosphere, local food vendors, and fall-inspired entertainment, the Harvest Festival is the perfect way to embrace the season. Whether you’re enjoying the activities with your family or sampling some delicious homemade treats, this event is one of Woodbury’s most beloved traditions.
6. Woodbury Classic Car Show: A Tribute to Vintage Automobiles
For car enthusiasts, the Woodbury Classic Car Show is a standout event. Held each summer, this show brings together classic car collectors and admirers from all over the region to showcase their vintage vehicles. From sleek muscle cars to timeless classics, the car show offers a stunning array of automobiles to admire and appreciate.
In addition to the car displays, the show features food vendors, live entertainment, and family-friendly activities. Whether you’re a car collector or simply a fan of vintage automobiles, this event is an exciting way to spend the day in Woodbury. It’s also a great opportunity to meet fellow car enthusiasts, learn about the history of different models, and enjoy a fun day out with the family.
7. Woodbury Art Walk: Discover Local Artists and Creativity
Woodbury’s creative community takes center stage during the Woodbury Art Walk, an event that showcases the work of local artists. Held several times throughout the year, the Art Walk invites visitors to explore galleries, studios, and public spaces displaying a variety of artwork, from paintings and sculptures to photography and mixed media.
The Art Walk is not only a chance to view art, but also an opportunity to engage with local artists and learn about their creative processes. Many of the participating artists offer live demonstrations and workshops, giving visitors a behind-the-scenes look at how their artwork comes to life. Whether you’re an art lover or just interested in exploring Woodbury’s creative scene, the Art Walk is a must-see event.
8. Woodbury Holiday Village Stroll: A Winter Wonderland of Lights and Cheer
When December arrives, the town of Woodbury transforms into a winter wonderland with the Holiday Village Stroll. This festive event kicks off the holiday season with a stroll through the town’s historic district, where visitors can enjoy the twinkling lights, holiday decorations, and special shopping deals at local stores.
The tree lighting ceremony is the highlight of the event, where the community gathers to watch the town’s holiday tree come to life with sparkling lights. Visitors can also enjoy carolers, visits from Santa Claus, and other holiday-themed activities. The Holiday Village Stroll is the perfect way to get into the holiday spirit and experience the magic of Woodbury during the most wonderful time of the year.
9. Woodbury Turkey Trot: A Thanksgiving Day Tradition
For those looking to stay active during the Thanksgiving holiday, the Woodbury Turkey Trot is a fun and festive way to start the day. Held on Thanksgiving morning, this 5K run/walk is a family-friendly event that attracts participants of all ages and abilities. The Turkey Trot is a great way to burn off some calories before enjoying a traditional Thanksgiving meal, all while supporting a good cause, as proceeds benefit local charities.
Participants are encouraged to wear fun, Thanksgiving-themed costumes, adding to the lighthearted and festive atmosphere. Whether you’re running for a cause or just walking with family and friends, the Turkey Trot is a wonderful way to kick off the holiday season in Woodbury.
Conclusion: Woodbury, CT – A Year-Round Destination for Fun and Festivities
Woodbury, Connecticut, is a town that truly shines through its diverse range of events and activities. Whether you're celebrating the changing seasons, enjoying live music, or immersing yourself in the arts, Woodbury, CT events offer something for everyone. From the winter magic of Winterfest to the festive cheer of the Holiday Village Stroll, the town’s events create unforgettable memories and a sense of community.
As you plan your visit to Woodbury in 2025, be sure to mark your calendar for these incredible events. Whether you’re exploring the beauty of the Spring Garden Tour or enjoying the fall flavors at the Harvest Festival, you’ll find that Woodbury is a place where every season is celebrated with enthusiasm and warmth.