Last Updated on September 12, 2017 by Minna Reid
August 28, 2017
Cheshire is a lovely and inviting small town in New Haven County, Connecticut.
Cheshire was incorporated in May, 1780 and named after the country of Cheshire, England. When the town was incorporated, it was predominantly a rural farming community. Over the last fifty years, the town has flourished into a highly desirable residential suburban community. Despite its industrial and commercial growth, Cheshire holds onto its rural characteristics with thousands of acres of well-maintained open space for everyone to enjoy.
This is a community where historic homes blend well with newer tree lined neighborhoods. This charming little town is nestled in the midst of several major cities of CT. It sits 14 miles North of New Haven, 25 miles south of the capitol, Hartford, 30 miles Northeast of Bridgeport and Waterbury is adjacent to Cheshire. Traveling around Cheshire is mainly done by care (with limited public transportation). Interstate 69 skirts the Northern edge of the town. Interstate 84 passes through the Northwest part of the town. The main North-South artery is CT Route 10. There are two East-West, Route 42 and Route 68/70. The J line of CT Transit New Haven, which runs from Waterbury to New Haven, does travel through Cheshire on Routes 70 and 10. A commuter express bus also runs from the commuter lot near I-84 to Hartford.
Cheshire is very near many main roadways, making it a good choice for those that commute and makes it easy for you to hop in your car and take some adventures to the many wonderful places that surround the area.
In 2009, Cheshire was ranked #72 in Money magazines “100 Best Places To Live”. Likewise, in 2011, Cheshire was ranked #73 in Money’s “100 Best Places to Live”. Passing through Cheshire, it’s easy to understand why. Its lush landscape, laid back atmosphere and friendly people make it a very desirable town.
Cheshire is very much a family focused community with an impeccable school system, top notch public safety and an abundance of well-kept open space to enjoy and reconnect with nature. Cheshire is a great place to raise a family and the schools are a main priority for the community. Cheshire is home to one public high school and one public middle school. There are four public Elementary schools as well as several private and alternative schools in town. Education is such a high priority with true quality and an incredible amount of resources available to each student.
Because Cheshire is so well kept, you would be hard pressed to find litter in the street or parks that aren’t in stellar condition. There are so many great open spaces to explore, trails to hike and even water falls to enjoy. A personal favorite that comes to mind is Roaring Brook Falls, along the Quinnipiac trail. It is in the Southwest corner of town and is Connecticut’s tallest single drop waterfall and is owned by the Cheshire land trust.
What I have come to love about Cheshire is the quality of the parks, exemplary education, outdoor recreation, incredible scenery, genuinely friendly people and I cannot forget to mention, absolutely the best homemade ice cream! You can find the cool treats at Sweet Claude’s. This is one place that really stands out for making all of their creative flavored ice cream on site and for offering homemade vegan flavors as well. There are plenty of benches outdoors to sit and enjoy the charming scenery and this quaint town feeling that seems to carry on in the air, down the picturesque streets and in the hospitality of the residents.