Cheshire Academy resides in the quaint New England town of Cheshire, CT. Close to New Haven and New York, Cheshire is a beautiful New England town near the hustle and bustle of two cities.

Though Cheshire Academy provides everything students might need on campus (including our own library, art gallery, and school store), students are welcome to explore the nearby Cheshire downtown in their time off. We encourage visiting families to explore the restaurants and shops that are in walking distance from campus, listed below.

Students find the town of Cheshire to contain many hidden gems like local coffee shops, art venues, and more. Our student resources page provides an in-depth guide to these much-loved locales. 

List of 8 items.

  • Directions

    From I-84
    Exit 27 (691 East) to Rt. 10 exit. Turn right. Follow Rt. 10 south for 4 miles. Cheshire Academy is just beyond the Maplecroft Shopping Center. Turn left at the next light into the campus entrance.

    From I-95 (to I-91 North)
    Follow I-91 North to exit 10 (Rt. 40 connector). Follow to Rt. 10. Turn right at the end of the connector toward Cheshire. Follow for 8 miles. Turn right into the campus entrance at the second light after the Cheshire Town Green.

    From Rt. 15 (Merritt Parkway)
    Exit 61 (Whitney Avenue/Rt. 10), turn right. Continue on Rt. 10 for 8.5 miles. Turn right into the campus entrance at the second light after the Cheshire Town Green.

    From I-91 (North of Meriden, CT)
    Exit 18 (691 West) to Rt. 10 exit. Turn left, follow Rt. 10 South for 4 miles. Cheshire Academy is just beyond the Maplecroft Shopping Center. Turn left at the next light into the campus entrance.
  • Transportation

    Cheshire Academy is within easy access of JFK International Airport in NYC and Bradley International Airport in Connecticut

    Connecticut Limousine Service runs regularly from JFK, LaGuardia, and Bradley airports to New Haven and Waterbury. 

    Train service runs regularly to New Haven from Grand Central Terminal and Penn Station in New York.

    Within the New Haven area, there is a local bus service with 20 different lines. You can view the lines and bus schedule on the CT Transit website.
  • Nearby Hotels

    Courtyard by Marriott, Wallingford
    203.284.9400

    Fairfield Inn, Wallingford
    203.284.0001

    Hilton Homewood Suites, Wallingford
    203.284.2600

    Courtyard by Marriott, Waterbury
    203.596.1000

    Four Points by Sheraton Hotel, Meriden 
    203.238.2380

    Hampton Inn by Hilton, Meriden
    203.235.5154

    Holiday Inn, North Haven 
    203.239.6700

    Inn at Middletown, Middletown
    860.854.6300
  • Meriden Restaurants

    Huxley’s (Breakfast/Lunch)
    1333 E. Main St.
    203-237-4087
     
    Lido’s Restaurant and Pizzeria
    75 Pomeroy Ave.
    203-634-3959
     
    Gianni’s
    1241 E. Main St.
    203-235-0230
     
     
    Ruby Tuesday
    470 Lewis Ave.
    203-630-1703
     
    Silver City Grill (inside the Four Points Sheraton Hotel)
    275 Research Parkway
    203-608-7157
  • Waterbury Restaurants

    Frankie’s Hotdogs
    700 Watertown Ave.
    203-753-2426
     
    Brass City Bistro
    812 Hamilton Ave.
    203-574-2489
     
    Texas Roadhouse
    330 Reidville Dr.
    203-757-0544
    Avventura Deli
    72 America St.
    203-574-1274
     
    Sultan’s Turkish Restaurant
    586 Plank Rd.
    203-591-8450
     
    Diorio Restaurant & Bar
    231 Bank St.
    203-754-5111
  • Cheshire Restaurants

    150 Main Street
    203-272-0591

    The Funky Monkey Café
    130 Elm St.
    203-439-9161

    Cheshire Coffee
    210 Old Towne Rd.
    203-271-3370

    Bagelicious Bagels
    945 S. Main St.
    203-250-9339

    Rossini’s Italian Restaurant & Pizza
    529 West Main St.
    203-272-7297

    Viron Rondo Osteria
    1721 Highland Ave
    203-439-2727

    Bellagio Ristorante & Pizza
    839 W. Main St.
    203-439-9175

    Watch Factory Restaurant (German)
    122 Elm Street
    203-271-1717

    286 Maple Avenue
    203-272-2441

    226 Maple Avenue
    203-272-5743

    460 West Main Street
    203-272-8400
  • Wallingford Restaurants

    Ihop (International House of Pancakes)
    930 No. Colony Rd.
    203-269-9901

    Bruegger’s Bagels
    970 N. Colony Rd.
    203-269-5666

    Chili’s Grill & Bar
    200 Church St.
    203-697-9313

    Gaetano’s Tavern on Main
    40 N. Main St
    203-294-1114

    Michaels Trattoria
    344 Center St.
    203-269-5303

    99 Restaurant
    914 N. Colony Rd.
    203-284-9989

    Wood N Tap
    914 N. Colony Rd.
    203-294-9591

    Westbrook Lobster House
    300 Church St
    203-265-5071
  • Additional Information/Other Useful Information

    Public Services:
    Cheshire Post Office
    210 Maple Ave.
    203-272-3594

    Cheshire Public Library
    104 Main St.
    203-272-2245

    Fitness:
    Fitness Express
    1020 S. Main St
    203-271-0400

    Physique Plus
    1303 Highland Ave.
    203-272-0014

    Grocery:
    Stop N Shop
    275 Highland Ave.
    203-272-5993

    Gas:
    Mobil
    996 S. Main St.
    203-271-3601

    Citgo Gas
    626 Maple Ave.
    203-271-1163

    Medical:
    Midstate Medical Center
    435 Lewis Ave.
    Meriden, CT
    203-694-8200

    Yale-New Haven Hospital
    20 York St.
    New Haven, CT
    203-688-4242

    Salon & Spa:
    Elle Salon & Spa
    471 W. Main St
    203-250-7333

    Rikeesa Salon & Spa
    16 Chipman Dr.
    203-272-1877

    Florist:
    Cheshire Nursery
    1317 S. Main St.
    203-272-3228

Connect

Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSIONS OFFICE: 203-439-7290
ADMISSIONS FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 
DEVELOPMENT OFFICE: 203-439-7307
DIRECTIONS | MAP | QUESTIONS | PRIVACY POLICY

About Cheshire Academy

List of 1 items.

  • 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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