Cheshire

About Cheshire

Nestled in the Naugatuck Valley of New Haven County, Cheshire is a welcoming suburban town with a strong sense of community and a surprisingly colorful identity. Known affectionately as the Bedding Plant Capital of Connecticut, it blends small-town charm with well-kept neighborhoods, excellent schools, and easy access to the broader Connecticut landscape. It's the kind of place where people put down roots — literally and figuratively.

What to Know

• The "Bedding Plant Capital" nickname is no joke — Cheshire has a long history of greenhouse and nursery farming, and horticultural businesses remain part of its local identity.
• The First Congregational Church of Cheshire is one of the town's most recognizable landmarks, a classic New England steeple anchoring the town green.
• Cheshire is home to the Cheshire Academy, a respected private boarding and day school with roots going back to 1794 — one of the oldest prep schools in the country.
• Outdoor lovers enjoy Sleeping Giant State Park on the town's southern border, offering miles of hiking trails and a distinctive ridgeline that resembles a reclining figure.
• The town operates under a council-manager form of government, keeping local administration professional and community-focused.

History

Cheshire was settled in 1694 and incorporated as a town in 1780, named after Cheshire, England. Its early economy was rooted in agriculture and trade, and the establishment of Cheshire Academy in the late 18th century gave the town an early reputation as a center of education and civic life.

Community & Living

Cheshire consistently ranks as one of Connecticut's most desirable places to raise a family, thanks to its highly regarded public school system and safe, walkable neighborhoods. Residents take pride in their town's balance of suburban convenience and genuine community spirit — from local farm stands to well-attended town events. It's a place that feels both grounded and quietly proud.