- Our list of the best things to do in Cheshire, Connecticut, features the top 451 nearby activities — including 186 great attractions with user approval ratings of 90% or more!
- Cheshire, CT has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Museums & Galleries, Entertainment & Shows, and Sights & Landmarks.
- The results below include the top 10 things to do within the city of Cheshire, CT , followed by 441 popular activities in nearby cities, including New Haven, Hartford, West Hartford, Hamden, Middletown, Wallingford, Bristol, Waterbury, Milford, Branford, Newington, Guilford, Wethersfield, New Britain, Farmington, Torrington, Bloomfield, Madison, Southington, Trumbull, Stratford, West Haven, East Haddam, Woodbury, Litchfield, Southbury, Avon, Clinton, Shelton, Glastonbury, Meriden, New Hartford, East Hartford, Simsbury, Naugatuck, Washington Depot, South Windsor, Plantsville, Mashantucket, Windsor, Manchester, East Haven, Washington and Goshen
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40.2 Miles
Featuring 32 synthetic lanes, Carmel Bowl offers open and league bowling with automatic scoring and bumpers. The center provides a pro shop and private event hosting along with arcade and redemption games.
40.3 Miles
The tasting room of Bedell Cellars is within a renovated historic barn and features daily tastings. Tours of the site can be arranged but they need to be booked several days in advance.
40.3 Miles
As a remnant of the 19th century, Old Field Pt Lighthouse is a granite building in use by the Coast Guard. The lighthouse isn't open to tours, but can be viewed from the outside during certain open grounds events.
40.5 Miles
A part of the Bowlmor family, AMF Rip Van Winkle Lanes is a fun and exciting entertainment locale in Norwalk. Along with bowling, guests can enjoy other games and activities including laser tag, bocce and miniature golf.
40.5 Miles
Coffee Pot Cellars Tasting Room is a small-production winery with connections to the beekeeping world that features beeswax and honey products in addition to their wines. They also occasionally host live music.
40.5 Miles
Producing 5 different varieties of wines, Coffee Pot Cellars is a winery that also makes handcrafted products including candles, crayons, and lip balm. The winery has a tasting room that is open Friday through Monday.
40.5 Miles
Founded in 1991, the Harbor Ballet Theatre is a not-for-profit ballet company that stages professional ballet productions. The theatre is notable for its annual performance of The Nutcracker and aims to provide young dancers with a professional environment.
40.6 Miles
The Peconic Bay Winery was founded in 1979 and offers an extensive variety of wines, hard cider, and grape brandy. Outdoor live entertainment is presented during the summer months and harvest season, but the actual tasting room is located off-site.
40.6 Miles
Theater Confections Inc is a financial company that offers financing for theater renovation and expansion, comprehensive assistance, and theater construction. The company also provides consulting for ski resorts and state parks.
40.7 Miles
Now owned by the Galluccio Estate, Gristina Vineyards is a well-known Long Island vineyard and winery. An 87 acre vineyard with 30 acres devoted to active grape cultivation, Gristina Vineyards makes an array of wines.