Best of Cheshire, CT
The best restaurants, cafés, bars, shops and things to do in Cheshire, CT — mapped and organized by category.
About Cheshire
Cheshire is a town in New Haven County, Connecticut, United States, and part of the Naugatuck Valley Planning Region. With a population of 28,733 at the time of the 2020 census, it holds a unique geographic distinction. The center of population of Connecticut is located in Cheshire.
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Roaring Brook Falls
Located in Strathmore Woods, Roaring Brook Falls features an 80-foot horsetail cascade formed by Roaring Brook descending a wooded cliffside on West Mountain. It is recognized as one of the tallest waterfalls in Connecticut.
The waterfall is situated in the southwestern hills of Cheshire, Connecticut.
View details →Best Hotels in Cheshire
1 places · Where to stay, from budget-friendly to boutique.
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Cheshire Welcome Inn
Cheshire Welcome Inn is a hotel located in the Strathmore Woods neighborhood.
Best Restaurants in Cheshire
5 places · Where to eat, from neighborhood staples to standout kitchens.
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Viron Rondo Osteria
Viron Rondo Osteria is a restaurant located at 1721 Highland Avenue.
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Cheshire Pizza and Ale
Cheshire Pizza and Ale serves pizza and Greek dishes at 127 Highland Avenue.
Best Cafés & Coffee in Cheshire
1 places · Coffee shops, roasters and casual spots to linger.
Best Things to Do in Cheshire
2 places · Museums, landmarks and the experiences worth your time.
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Barker Character, Comic, & Cartoon Museum
Barker Character, Comic, & Cartoon Museum is located in the Meadowbrook neighborhood.
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Roaring Brook Falls
Located in Strathmore Woods, Roaring Brook Falls features an 80-foot horsetail cascade formed by Roaring Brook descending a wooded cliffside on West Mountain. It is recognized as one of the tallest waterfalls in Connecticut.
Best Shops in Cheshire
1 places · Independent boutiques, bookstores and places to browse.
Best Parks & Outdoors in Cheshire
14 places · Green space, gardens and room to breathe.
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Copper Valley Club
Copper Valley Club is a park situated in the Meadowbrook neighborhood.
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Diamond Hill Park
Diamond Hill Park is a public green space in the Meadowbrook neighborhood.
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McNamara Field
McNamara Field is a park located in the neighborhood of Meadowbrook. It offers green space for residents and visitors alike.
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Mixville Park
Mixville Park is a green space located in the Strathmore Woods neighborhood.
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Quinnipiac Recreation Area
Quinnipiac Recreation Area offers a variety of outdoor activities for visitors in the Meadowbrook neighborhood.
Nearby cities to explore
More guides within driving distance of Cheshire.
- Cheshire Village, CT 1 places
- Prospect, CT 6 places
- Wallingford, CT 72 places
- Meriden, CT 126 places
- Southington, CT 29 places
- Hamden, CT 84 places
- North Haven, CT 9 places
- Naugatuck, CT 33 places