Founded in 1794, Cheshire Academy is a coeducational boarding and day school located in Historic Cheshire Village in Connecticut. Serving students in grades 8-12 and postgraduates, this 104-acre campus is the ideal setting for an independent school. The town of Cheshire provides numerous amenities within walking distance, including a grocery store, shopping destinations and several restaurants and coffee shops, as well as the on-campus amenities, including a fitness center, student center with snack bar, pool, school store and more.

Life at Cheshire Academy has everything you could possibly want, including all of your friends in one place, teachers available for help at odd hours, and local restaurants and shops, all within walking distance. From weekend activities on campus and trips off-campus with faculty members, to playing foosball and grabbing a snack in the student center, there’s always something happening.

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  • Coffee and Convenience Stores

    Cheshire Coffee is just two blocks south of the campus in a historic building. Cheshire Academy students have a special connection to the establishment, with two student photography shows exhibited on the walls during the 2013-14 school year. Their flavored lattes, chai tea lattes and hot chocolate, as well as their selection of delicious baked goods, are favorites among the students.

    Head a couple blocks south of Cheshire Coffee, and you’ll find a 7-Eleven with all your convenience store needs, including ice cold Slurpees.

    Just a bit further south on Main Street you’ll find Dunkin’ Donuts, a New England favorite. Donuts, coffee, lattes and hot cocoa are big hits on campus. If you’re lucky, sometimes your teachers will even pick up a box of munchkins for class or study hall.
  • Maplecroft Plaza

    From groceries to bargain shopping, the Maplecroft Plaza has most everything our students need, and all of it within walking distance of the campus. Located just north of campus on Highland Avenue, this plaza is home to several restaurants, banks and stores, making it a one-stop-shopping experience for many students.

    One of the Northeast’s largest grocery chains, Stop & Shop, is a main attraction for students, where they stock up on personal care items, snacks and more. This Stop & Shop has a deli, pharmacy, produce and natural food sections as well as a florist. It also is home to a Redbox movie rental kiosk and People’s Bank, including an ATM. Several other banks are located within this Plaza, as well.

    Subway restaurant, Mr. B’s Pizza, a frozen yogurt shop and The Waverly Restaurant make up the dining options here. Additional restaurants can be found outside of the Plaza, many of which provide food delivery options for students.  

    Shopping here comes in the form of Denali’s and Marshall’s. There is also a dry cleaner’s, hair salon, and nail salon located in the Plaza.

  • The Watch Factory and Nearby Shoppes

    The Watch Factory has a long history with Cheshire Academy, having once been part of the campus. Dorms and classrooms have since been renovated and turned into a thriving array of shops and local businesses.

    A popular hangout for students at the Watch Factory is the Funky Monkey Cafe & Gallery. In addition to a wide variety of food and coffee items, including desserts, gluten free options and vegetarian selections, the Funky Monkey also showcases local artwork. Visit the shop on the right night, and you may even be treated to live music or a comedy show.

    Nearby, you’ll also find Thai food, pizza, and more, all right across the street from campus.


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSIONS FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

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  • The student-centered private school in CT

    Cheshire Academy is a boarding school in Connecticut that challenges students in grades 9-12 and Post Grad to discover and hone their unique talents. This college preparatory school offers personalized learning opportunities like the Roxbury Academic Support Program and the IB Program. Artists can benefit from the Art Major program, while high school athletes can benefit from competitive athletics. Overall, students at the private school are encouraged to become culturally sensitive and internationally minded, and develop the critical thinking skills, confidence, and character that enable them to succeed in college and as citizens of a global society. 
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