Living in Cheshire, CT

About the Area

Conveniently located in between New York and Boston, and only 15 miles from downtown New Haven, our community offers the finest nearby attractions with a unique flair for modern country living. Everything from golfing to high end boutiques is right at your fingertips to accommodate your active lifestyle. Choosing Cheshire for your new home construction is easy when factoring in all the benefits life in Cheshire has to offer. Resident of Castle Heights enjoy the privacy of a planned 55+ community while still being near major cities including Hartford, Boston and New York and plenty of entertainment and attractions. The custom homes that make up Castle Heights include the highest energy efficient standards, expert craftsmanship and award winning designs that combine to make your new home in Cheshire a relaxing place to be. At Castle Heights you can enjoy the quiet and serene surroundings of our active adult community or venture out to explore the many attractions that Cheshire has to offer.


Cheshire is located in between Hartford and New Haven which are both epicenters for arts, music, and nightlife. Some of the main attractions in the area include the Barker Character, Comic & Cartoon Museum, Sleeping Giant State Park, the Mount Southington Ski area and the Laurel View Country Club.


Cheshire is located amid some of the best shopping in southern CT. Outlets, boutiques, malls, and specialty shops are just a short ride away. Castle Heights provides you with the privacy you want and the convenience you need.


Castle Heights offers its own local attractions including its very own book club as well as a men’s and women’s golf club. We strive to make all of our active adult communities places of privacy and activity so residents can enjoy quiet country living while also interacting with other active adults. There are several museums and parks nearby, and the Connecticut shore is only a 25 minute drive away. With so many exciting places to visit, you are sure to find adventure, either on your own or with the friends you are sure to make in your new community here at Castle Heights. In Cheshire is the famous Sleeping Giant State Park which has numerous hiking trails, a lookout tower, stream fishing and campgrounds. A 1.5 mile scenic trail leads to the stone observation tower on the peak of Mt. Carmel which provides an excellent view of Long Island Sound and New Haven. Other nearby parks include West Rock Ridge State Park in Hamden and Wharton Brook State Park in Wallingford.


The Cheshire Public Schools extend a warm welcome and a sincere invitation to all those who are considering a move to Cheshire to visit our schools and to participate as an active partner for educational excellence. The Cheshire public school system includes Norton Elementary, Highland Elementary, Doolittle Elementary, Chapman Elementary, Darcey Kindergarten, Dodd Middle School and Cheshire High School.Cheshire enjoys a well-deserved reputation for excellence throughout all of our programs from early childhood through grade 12. The town strives for the continued excellence of the programs. Cheshire schools constantly review and analyze the programs and strengthen them where necessary so that it can prepare their children to meet the challenges of the new millennium. The town of Cheshire hopes you will become familiar with our schools and participate in our programs, as we, together, assure the finest possible educational opportunities for all of Cheshire’s youth.


Cheshire, in its close proximity to Yale in New Haven, has some of the country’s best medical facilities close by. These include: Gaylord Rehabilitation in Wallingford, St Mary’s Hospital, Yale New Haven Hospital, St. Rapheals, and the Joslin Diabetes Center.


When Cheshire was originally settled by Europeans, it was part of the town of Wallingford and known locally as “Northfarms”. In 1780, Cheshire separated from Wallingford to become its own town, and for the next 170 years, Cheshire remained a small but prosperous farming town.

Cheshire, Connecticut is a residential community located in New Haven County. Cheshire, originally a part of the Town of Wallingford, was settled in 1694 and incorporated as a Town in May of 1780. Cheshire is easily accessible from Interstates 84, 91 and 691 and state routes 70, 68, and 10. The Town is bounded on the north by Southington and Wolcott, on the east by Meriden and Wallingford, on the south by Hamden, and on the west by Prospect and Waterbury.

For its first 170 years, Cheshire was predominantly a rural farming community. During the past 50 years, the Town has become a residential suburban community. Despite significant industrial and commercial growth, Cheshire retains its rural characteristics with thousands of acres of open space and an active agricultural industry. In fact, Cheshire has been designated the “Bedding Plant Capital of Connecticut” by the Connecticut General Assembly because of its bedding plant growers.

Every June, the town celebrates its annual Strawberry Festival on the First Congregational Church green. The Barker Character, Comic and Cartoon Museum, located in the northern section of Cheshire, holds a large collection of memorabilia, novelties and ephemera such as lunch boxes and PEZ dispensers bearing the likenesses of characters from television, cartoons and comics.

Useful Links

Town of Cheshire
Cheshire Schools
Cheshire Regional Rehab Center

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