Winchester, a charming town nestled in the southern Berkshires, is known for its high quality of life and breathtaking natural surroundings. From lakes and ponds to brooks and wooded hills, Winchester offers a diverse range of outdoor activities for nature enthusiasts. At the same time, Winchester’s Winsted section exudes a small city vibe with its historic mill town roots and vibrant arts community.
In this comprehensive guide, we’ll dive into the top 15 things to do in and around Winchester, Connecticut. Whether you’re a history buff, outdoor adventurer, or art aficionado, Winchester has something for everyone. So sit back, relax, and let’s explore this hidden gem of a town together!
Discover Winchester’s Rich History and Architecture
1. Town Green National Historic District
- Immerse yourself in Winchester’s rich history by visiting the Town Green National Historic District, where you can explore the oldest buildings dating back to the early 19th century.
- Don’t miss the iconic Gideon Hall, Jr. House with its striking Greek Revival architecture.
- Stroll through the town’s commercial district lined with turn-of-the-century buildings, antiques shops, restaurants, and a charming bistro-cinema.
2. Solomon Rockwell House
- Step back in time at the Solomon Rockwell House, home to the Winchester Historical Society.
- Explore the Greek Revival mansion and learn about Winchester’s industrial heritage and Civil War artifacts.
- Marvel at the impressive Ionic portico of the main block and explore the museum’s ten rooms filled with fascinating exhibits.
3. Soldiers’ Monument and Memorial Park
- Pay homage to the heroes of Winchester at the Soldiers’ Monument and Memorial Park, dedicated to those who fought in the Civil War.
- Admire the grand Medieval-style tower and bronze soldier figure overlooking the park.
- Experience the recent renovation funded by generous donations that have preserved this historic landmark for future generations.
Dive into Winchester’s Vibrant Arts and Culture Scene
4. Whiting Mills
- Visit Whiting Mills, a historic mill complex that houses a diverse community of artists, craftsmen, and health practitioners.
- Explore the studios of painters, potters, photographers, and more, and witness creativity in action.
- Attend one of the semi-annual open days to interact with artists, attend workshops, and engage in thought-provoking conversations.
5. American Mural Project
- Immerse yourself in the American Mural Project, a collaborative art project led by artist Ellen Griesedieck.
- Discover the world’s largest mural dedicated to American workers, measuring over 35 meters in length.
- Witness the ongoing creation of this monumental masterpiece by thousands of artists and volunteers from across the country.
6. Gilson Cinema & Cafe
- Experience a unique blend of cinema and dining at Gilson Cinema & Cafe, where you can enjoy a movie and meal in one place.
- Indulge in a wide range of menu options, including soups, salads, burgers, and pasta dishes, served right to your seat.
- Sit back, relax, and enjoy a first-run movie with waiter service and a well-stocked bar for a memorable cinematic experience.
Explore Winchester’s Natural Beauty and Outdoor Adventures
7. Bridge Street/Prospect Street Rail Trail
- Take a leisurely stroll along the Bridge Street/Prospect Street Rail Trail, a scenic path tracing the Mad River through Winsted.
- Explore remnants of the New York, New Haven, and Hartford Railroad, along with informative plaques detailing the area’s history.
- Learn about the devastating flood of 1955 and enjoy a walk surrounded by nature and local landmarks.
8. Sue Grossman Still River Greenway
- Embark on a refreshing journey along the Sue Grossman Still River Greenway, a three-mile trail connecting Winchester and Torrington.
- Traverse wetlands, listen to the soothing sounds of the Still River, and immerse yourself in the natural beauty of the Berkshires.
- Keep an eye out for local wildlife, including rabbits and deer, as you meander through this serene landscape.
9. Highland Lake
- Escape to the tranquil waters of Highland Lake, a picturesque 440-acre lake perfect for boating, fishing, and swimming.
- Enjoy the natural beauty of wooded hills, multiple streams, and seasonal residences dotting the shoreline.
- Launch your boat from the state boat ramp or relax on the town-maintained beaches for a day of fun in the sun.
10. Platt Hill State Park Scenic Reserve
- Unleash your inner explorer at Platt Hill State Park Scenic Reserve, a nature reserve overlooking Highland Lake.
- Wander along unmarked trails, soak in the sights and sounds of the Connecticut landscape, and discover hidden gems along the way.
- Pack a picnic, admire the wildflowers in summer, and relish the tranquility of this scenic paradise just a stone’s throw from Winchester.
Indulge in Winchester’s Culinary Delights and Craft Brews
11. Norbrook Farm Brewery
- Experience the local craft beer scene at Norbrook Farm Brewery, a community favorite in Colebrook.
- Savor signature beers like American IPA, Saison, and Farm Day IPA brewed with locally sourced ingredients.
- Enjoy picturesque views of the Berkshires from the taproom, where you can sample tasters and explore a rotating tap list.
12. Laurel Duckpin Bowling Lanes
- Add a touch of nostalgia to your Winchester experience at Laurel Duckpin Bowling Lanes, where you can enjoy a classic game of duckpin bowling.
- Challenge your friends to a game on Main Street in Winsted, complete with retro pinball machines and old-school charm.
- Experience the unique mechanics of duckpin bowling, where precision and skill are key to scoring a strike.
Conclusion
From historic landmarks and cultural attractions to outdoor adventures and culinary delights, Winchester offers a diverse range of experiences for visitors of all ages. Whether you’re a history buff, nature lover, art enthusiast, or beer connoisseur, this charming town has something special waiting for you. So pack your bags, hit the road, and explore the best of Winchester, Connecticut today!