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Nurseries and greenhouses earned Cheshire its old nickname, the Bedding Plant Capital of Connecticut, and the town still feels like a green, unhurried place between Waterbury, Meriden and New Haven. Colonial houses line the long town green, white steeples rise above the maples, and roadside garden centers burst into color every spring.
Settled in the late 1600s as part of Wallingford, Cheshire became its own town in 1780. The Farmington Canal cut through in the 1820s, and Lock 12, one of its best surviving locks, has been restored as a small historical park. Later a trolley line crossed the hills, and its stone abutments and bridges can still be found in the woods. Cheshire Academy, founded in 1794, is one of the oldest boarding schools in the country.
Today visitors come to cycle or walk the paved canal trail, hike to Roaring Brook Falls, browse the historical society's museum house and picnic beside Mixville Pond. New Haven's museums and Sleeping Giant State Park are a short drive south.
A small riverside park built around Lock 12 of the Farmington Canal, one of the best preserved locks of the 1820s waterway that once linked New Haven to Massachusetts. See the stone chamber, a lock keeper's house and a shady picnic lawn by the water. The paved canal trail passes right through.
In the early 1900s a trolley line linked Cheshire with Waterbury and Meriden, and its stone abutments, concrete bridges and raised railbed still survive in the woods near Notch Road and Grove Street. Some sections are crossed by trails. It is a fun hunt for history buffs; respect private property and stay on public paths.
The flat, paved trail follows the old canal and railroad bed across Cheshire, shaded by trees and dotted with wetlands where herons feed. It is popular with cyclists, runners and families with strollers. Start at Lock 12 Historical Park, where there is parking, and ride north toward Southington or south toward Hamden.
Cheshire's town park surrounds Mixville Pond, with a small swimming beach in summer, picnic pavilions, a playground and easy trails through the woods. It is a pleasant place for a family afternoon or a lakeside lunch. Summer beach access and parking may require a town pass or day fee, so check the rules first.
A large town park off South Main Street with ball fields, a skate park, a playground, walking paths and open lawns. Seasonal town events and fairs are often held here. It is convenient for letting children burn off energy between sights, and the canal trail and town center are only a few minutes away by car.
Roaring Brook tumbles down a series of rock ledges in a wooded ravine, a waterfall often counted among the highest single drops in Connecticut. A short but rocky trail climbs beside it from a small roadside pull-off. Go after heavy rain or snowmelt for the best flow, wear grippy shoes and stay off the wet ledges.
The Cheshire Historical Society keeps its collections in this late 18th-century house near the green, with period rooms, local photographs, nursery and industry exhibits and changing displays on town life. Opening hours are limited and often by appointment or on weekend afternoons, so check the society's schedule before you go.
The historic heart of town stretches along Main Street and the long green, with Federal and Greek Revival houses, old churches and the academy buildings. It is listed on the National Register of Historic Places. Park near the town hall and stroll the sidewalks; autumn color under the old maples is especially lovely.
This graceful white meetinghouse with a tall columned portico and spire faces the town green and dates to the 1820s, replacing earlier churches of a congregation founded in colonial times. It is a classic New England scene and a favorite for photographs. The church is active, so view it from the green outside services.
Founded in 1794 as the Episcopal Academy of Connecticut, this is one of the oldest boarding schools in the United States. Bowden Hall and other brick buildings frame a leafy campus on Main Street across from the green. The grounds are private, so admire the architecture from the sidewalk unless you are visiting for an event.
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Photo: Pi.1415926535, Wikimedia Commons, CC BY-SA 4.0
Photo: Pi.1415926535, Wikimedia Commons, CC BY-SA 4.0
Photo: Pi.1415926535, Wikimedia Commons, CC BY-SA 4.0
Photo: Pi.1415926535, Wikimedia Commons, CC BY-SA 4.0
Photo: Pi.1415926535, Wikimedia Commons, CC BY-SA 4.0
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Photo: Kenneth C. Zirkel, Wikimedia Commons, CC BY-SA 4.0
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Photo: All About Cheshire Ct, Wikimedia Commons, CC0
Photo: All About Cheshire Ct, Wikimedia Commons, CC0
