- 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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22.1 Miles
Situated within a 4,000 acre nature reserve, the Big Cathedral Trail offers relatively smooth travel for even the novice hiker. Visitors are also able to use the trail for cross-country skiing and snowshoeing in the winter.
22.1 Miles
An amphitheater with capacity for 30,000 people, XFINITY Theatre offers both outdoor lawn and indoor seating along with a concession area. The theater is home to events including concerts and festivals.
22.1 Miles
Spend some time outdoors at J.B. Williams Park. Facilities include a softball field, hiking trails and a playground. A pavilion, which includes a refrigerator, stove, sink and serving center, is available for rental.
22.1 Miles
An equestrian facility located on 30 acres of land, GMC Farm offers a variety of horse-related services. The facility cares for boarded horses, particularly older and retired ones, and offers riding lessons and guided trail rides.
22.1 Miles
A 300-acre park, Machimoodus State Park features a variety of landscapes, including woods, meadows, uplands, and waterfront areas. Visitors can bird watch, hike the extensive trails, or simply relax and take in nature.
22.1 Miles
Spanning 300 acres, Machimoodus State Park is composed of woodlands, rivers, cove waterfronts, and scenic hiking trails. Picnic areas and pit toilets are available, and birdwatching, fishing, and horseback riding are permitted.
22.2 Miles
At XFINITY Theatre, visitors can see a wide variety of live entertainment, from touring comedians to nationally recognized musicians. The theater features both an indoor and outdoor seating area that can seat up to 30,000 people.
22.2 Miles
Visitors to Addison Park can choose from a number of available recreational activities, including outdoor basketball courts, softball fields, soccer and lacrosse fields. Also offered are picnic areas and an outdoor swimming pool.
22.3 Miles
Visitors to Silver Sands State Park in Milford, Connecticut enjoy fishing, swimming, shell collecting and other open-air activities. Entry is free. Swimming is allowed during daylight, but anglers may fish at any time.
22.6 Miles
At Milford Ice Skating Pavilion, visitors can participate in hockey leagues or learn how to skate during a skating lesson. The pavilion has birthday party packages that include a party room and admission to the rink.