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Location, Location, Location!

Where is Cheshire Academy?

In Cheshire, Connecticut.

Where is that?

Good question.

Location is everything. We love being a school set in the beautiful scrolling landscape of Southern Connecticut—just 2 hours from New York City and Boston, but even closer to many more of the exciting cities, state parks and beaches that Connecticut has to offer.

Downtown New Haven!

And we take advantage of it! Weekend activities abound with trips to downtown New Haven and the state capital, Hartford, for restaurant outings, shopping, theatrical and musical performances, art exhibitions, movies, and sightseeing.

When you get tired of the urban scene, you can organize a trip to go hiking at nearby Sleeping Giant State Park, or downhill skiing at several nearby mountains, or even get lost in Cheshire’s back yard: we have 104 acres of land, complete with a ropes course and fishing pond (warning: legend has it that we may or may not have snapping turtles, so the indoor pool may be your best bet for swimming!) If it’s really hot, a trip to Hammonasset Beach

Catching a trout dinner near Old Saybrook

may be in order! Our Director of Student Activities, Jessica Barry, is always open to suggestions for creating weekend fun.

Want to keep it local? The town of Cheshire is its own picturesque village, dotted with shops, cafés and boutiques and ‘mom & pop’ restaurants across the street from campus. Our students love to order take-out on weekends, or walk to the local grocery store to stock up on late night snacks. On-campus activities like movies under the stars, open-swim, concerts, in-door soccer tournaments, multi-school dances and pep-rallies occur year-round. Under the lights football games in the fall are definitely a highlight!

Another bonus? We have seasons.  Classic New England reds, oranges and greens in the foliage surrounding campus in the autumn, silent (and not so silent) snowfall blanketing the Academy in winter, pale buds exploding and the ice cream truck stalking unwitting students in spring (ok, so maybe its us stalking the ice cream truck...)

Movie night on-campus!

Always room for a friend!

You can find us here, but if you want to hear more about how—and where—students spend their free time at CA, let us know, and we’ll put you in touch with a current student!

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Carrie Moores

Written by Carrie Moores

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