First Congregational Church of Cheshire

The Cheshire Historic District encompasses the historic town center of Cheshire, Connecticut. Centered on the junction of Main Street and Academy Road, the district's architecture is reflective of the town's development over two centuries, and includes many of its civic buildings. It was listed on the National Register of Historic Places in 1986.

Cheshire Village is a census-designated place (CDP) comprising the primary village and adjacent residential land in the town of Cheshire, New Haven County, Connecticut, United States. It is in the center of the town, surrounding the intersections of Connecticut Routes 10, 70, and 68. As of the 2010 census, the CDP had a population of 5,786, out of 29,261 in the entire town of Cheshire.

Cheshire Academy is a selective, co-educational college preparatory school located in Cheshire, Connecticut, United States. Founded in 1794 as the Episcopal Academy of Connecticut, it is currently the eleventh oldest boarding school in the United States. In 1917, the school was renamed The Roxbury School, and trained young men exclusively for the purpose of attending nearby Yale University. Later known as Cheshire Academy, the school was the first private academic institution to accept international students dating back to the 1850s, and it is currently the only independent school to offer the International Baccalaureate Diploma Programme in the state of Connecticut.The Academy currently enrolls 344 students from approximately 31 countries and 19 states in grades 9 through 12 plus a postgraduate year.

Cheshire High School is a comprehensive public high school serving approximately 1,538 students; it is the sole comprehensive high school of Cheshire Public Schools. Located at 525 South Main Street in Cheshire, Connecticut, Cheshire High School is 15 miles (24 km) north of New Haven and 25 miles (40 km) south of Hartford. It is the town's sole public high school. As of 2016, Cheshire High School has approximately 1,538 students, 104 faculty members, six guidance counselors, three assistant principals, and one principal. The school is accredited by the New England Association of Secondary Schools and Colleges.

Cheshire ( CHEH-shurr), formerly known as New Cheshire Parish, is a town in New Haven County, Connecticut, United States. At the time of the 2020 census, the population of Cheshire was 28,733. The town is part of the Naugatuck Valley Planning Region. The center of population of Connecticut is located in Cheshire.

Cheshire Correctional Institution is a Connecticut Department of Correction state prison for men located in Cheshire, New Haven County, Connecticut. The facility was built beginning in 1910, partly by the inmates of the Wethersfield State Prison, and opened in 1913 as the Chester Reformatory for male youths ages 16 to 24. In 1982, the state's Manson Youth Institution opened adjacent to the Cheshire Correctional Institution, which was re-designated as an adult prison.The current capacity of Cheshire Correctional Institution is 1580 inmates.

Farmington Canal State Park Trail is a Connecticut state park forming a portion of the Farmington Canal Heritage Trail in the towns of Cheshire and Hamden. The developed section of the trail within state park boundaries runs over 17.0 miles (27.4 km) from Lazy Lane in Southington to Todd Street in Hamden and includes the historic Farmington Canal's restored Lock 12, located south of Brooksvale Road in Cheshire. The paved, multiple-use trail is used for hiking, biking, jogging, in-line skating and cross-country skiing.

Manson Youth Institution is a Connecticut Department of Correction state prison for men under the age of 21. It is located in Cheshire, New Haven County, Connecticut. Although it has a capacity of 679, it currently houses less than half that (322 as of June 2019).

Roaring Brook Falls is a waterfall in the southwestern hills of Cheshire, Connecticut in the Northeastern United States. Formed as the eponymous Roaring Brook descends a wooded cliffside on West Mountain, the waterfall is an 80-foot horsetail and ranks as one of the tallest in the state.

Brooksvale Park is a municipal park in the northwestern corner of Hamden, Connecticut, in the Northeastern United States. It covers an area of over 500 acres and is operated by the Hamden Parks and Recreation Department. The park is home to a wide variety of recreational activities and natural features, including hiking trails, fishing ponds, a nature center, community garden and a working farm.The park shares a border with the Mt. Sanford Block of Naugatuck State Forest to the west and is connected via a cross walk across Brooksvale Avenue with the Farmington Canal State Park Trail to the east. Cheshire Connecticut adjoins the park's northern border.