Roaring Brook Falls

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.

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.

Prospect is a town in the Naugatuck Valley Planning Region, Connecticut, United States. It is a suburb of the nearby city of Waterbury to its north, and is on the north-eastern fringes of the New York metropolitan area. The population was estimated to be 9,401 in 2020. Prospect is part of the Waterbury NECTA and of the historical New Haven County. Prospect is also a member of the regional health district Chesprocott, along with Cheshire and Wolcott.Prospect was incorporated as a town in 1827 from the South Farms part of Waterbury and the West Rocks part of Cheshire. Prospect is an exurban town, with residents often traveling to other major cities and employment centers across the state.Prospect is known locally as being "The Best Small Town in Connecticut," with the phrase posted on the town's trucks and website. The name originates from an early 1990s article in Connecticut Magazine which ranked Prospect as the worst small town in the entire state. The measurement was done based on its school system, economy, the cost of living, crime rate and cultural resources. In response to this, the town's long-time mayor Robert Chatfield, removed the magazine from the library, and declared Prospect "The Best Small Town in Connecticut," and ordered it placed on town vehicles and bumper stickers.

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.

Prospect Green Historic District is a historic district in the New England town of Prospect, Connecticut. The district is centered on the Prospect Green, the town green. The green is located on the highest settled point in New Haven County. The green is bounded by Route 68 and Center and Church Streets.The main feature of the green is a Civil War Soldiers Monument (1907) situated near the center. Near it is a flag pole and another memorial. At the north end of the green is the former town library built in 1903-1904. Several historic buildings surround the green including, the current Congregational Church (built in 1941 and the fourth church on the site), the Grange Hall (1947), the Parsonage (1941), a 19th-century residence once used as a parsonage, and a school house (c. 1865, now used by the local historical society).The town of Prospect was settled in the 18th century and separately incorporated in 1827. Its town center arose in 1778, when the site, the highest in town, was selected for construction of a church. The town green was also laid out at that time, but remained in church ownership until 1905, when it was sold to the town. In the 19th century it developed as the civic heart of the town, with a Greek Revival school house built in 1867, and its first dedicated town library building (now the Meeting Place) built in 1905 as a gift of the Tuttle family. The library now occupies modern premises south of the church.

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.

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.

The David Hotchkiss House is a historic house museum at 61 Waterbury Road in Prospect, Connecticut. Built in 1820, it is a well-preserved example of Federal period architecture. Owned for 160 years by a single family, it has subsequently served as the headquarters of the local historical society. It was listed on the National Register of Historic Places in 1981.