Farmington Canal State Park Trail

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.

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.

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.

The First Congregational Church of Cheshire is a historic church at 111 Church Drive in Cheshire, Connecticut. Built in 1827, it was designed by David Hoadley and is a prominent local example of Federal period architecture. It was added to the National Register of Historic Places in 1973. The congregation is affiliated with the United Church of Christ.

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 ( 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.

WKCI-FM (101.3 MHz) is a commercial radio station broadcasting an adult-leaning Top 40 (CHR) format. Licensed to the suburb of Hamden, Connecticut, it serves New Haven and Hartford. The station is owned by iHeartMedia. The studios are in Radio Towers Park on Benham Street in Hamden, where it shares facilities with sister stations WELI and WAVZ. WKCI-FM transmits a full Class B signal, broadcasting with 12,000 watts from a 915-foot (279 m) tower, the equivalent of 50,000 watts at 500 feet (150 m). The station's transmitter is on Madmare Mountain in Hamden near the WTNH transmitter site (where WKCI-FM formerly transmitted from until moving to its current tower in 2003).Throughout the 1980s, WKCI was an affiliate of Rick Dees Weekly Top 40. WKCI-FM began broadcasts in HD Radio in December 2004. Its HD2 signal airs a mainstream urban format, providing a second option to WZMX, and is simulcast on FM translator W265DB at 100.9 MHz, known as "100.9 The Beat." 100.9 The Beat signed on the air at 12:00 a.m. on June 23, 2015. iHeartMedia, Inc. also owns a talk station in Waynesboro, Virginia which shares the call sign WKCI on AM 970.

Sleeping Giant (also known as the Blue Hills and Mount Carmel), (Hobbomock in Quinnipiac), is a rugged traprock mountain with a high point of 739 feet (225 m), located eight miles (13 km) north of New Haven, Connecticut. A prominent landscape feature visible for miles, the Sleeping Giant receives its name from its anthropomorphic resemblance to a slumbering human figure as seen from either the north or south. The Giant is known for its expansive clifftop vistas, rugged topography, and microclimate ecosystems. Most of the Giant is located within Sleeping Giant State Park. The mountain is a popular recreation site: over 30 miles (48 km) of hiking trails traverse it including 5 miles (8 km) of the 23-mile (37 km) Quinnipiac Trail. Quinnipiac University is located at Mount Carmel's foot in Hamden.