- 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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        45.8 Miles 
    
    
        
            
        
                                    89%
                19 votes
                            
			
            
                
                Westover Road, Stamford, CT 06902
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            Fort Stamford Park – Goodbody Garden offers photo opportunities for fans of perennial flowers. The location, which was also the home of a Revolutionary War-era barracks, is also a suitable destination for history buffs.        
    
    
        45.8 Miles 
    
    
        
        
            Featuring full digital projection and sound, Bow Tie Majestic 6 is a movie theater showing the latest released films to its guests. Visitors to the theater enjoy the many amenities provided, including concessions, closed captioning devices, and assisted listening devices.        
    
    
        45.8 Miles 
    
    
        
        
            Located in the Groton Shopping Mart, Hoyts Groton 6 Theatre offers showings of the latest big cinema releases. A perfect stop for rainy weather days, family night, or a date night.        
    
    
        45.9 Miles 
    
    
        
        
            As the taping location of daytime shows like Jerry Springer and Maury, Rich Forum Box Office provides visitors with the opportunity to be a part of the live audience for television shows in its theater.        
    
    
        46.0 Miles 
    
    
        
        
            Guided tours of Wing Castle and its grounds are available at regular times from Memorial Day to Labor Day. There is also an on-site bed and breakfast that embraces the style and decor of a European fairy tale.        
    
    
        46.1 Miles 
    
    
        
            
			
            
        
                
                Millbrook, NY 
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            The oldest permitted shotgun shooting club in the United States is the Orvis Sandanona Shooting Grounds. Traditions of the field and the hunt are held in high regard at the modern sporting clays shooting field.        
    
    
        46.1 Miles 
    
    
        
        
            With a variety of scenario courses to choose from, Cousins Paintball offers visitors a competitive space for paintball and airsoft. Each game is monitored by referees, who make decisions on which team has won the game.        
    
    
        46.2 Miles 
    
    
        
            
			
            
        
                
                26 Wing Road, Millbrook, NY 12545
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            Tours and wine tastings are offered daily at the Millbrook Vineyards & Winery throughout the year. From Memorial Day through October, guests can also visit the Vineyard Grill and Cafe to eat local gourmet food in a large tent near the pond.        
    
    
        46.2 Miles 
    
    
        
        
            Part of Adams Park, Adams Playground is a small area with swings, slides, a play structure and a spray pad. The park area has a full basketball court, benches under shade trees and open, grass fields for playing.        
    
    
        46.2 Miles 
    
    
        
        
            As a dog friendly beach, Esker Point Beach has a man-made beach with a sand volleyball court, picnic area, and swimming spots. Visitors can watch boats pass by and sunbathe by the shoreline.