Cheshire, New York - From the Family Album

Take a stroll down the Main Street of Cheshire, NY using historic and contemporary views.

Cheshire, New York - From the Family Album

Canandaigua, New York 14424, United States

Created By: Canandaigua Town Local History Team

Tour Information

Cheshire, New York, is a hamlet in the Town of Canandaigua, in New York's Finger Lakes region. Ever since it was settled in the 1790s by Connecticut pioneers and veterans of the American Revolution, it has been the business and social center for residents of the southern half of the Town. Cheshire grew by leaps and bounds during the 19th century, home to a school, a church, a meeting hall, a blacksmith, harness makers, a spoke factory, a cider mill, general stores and dealers in shoes and boots. Its property owners continue to use and maintain most of its 19th and early 20th century structures. Join us for a look at some of the historic places that give Cheshire its special character and charm, and test your powers of observation comparing an old print or photo with the same view today.

Unless otherwise indicated, historic images are from the photo collections of the Ontario County Historical Society.


Tour Map

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What You'll See on the Tour

The elegant Victorian home in this photo is well shaded by large maple trees and lush vines surrounding the front porch. The woman and her daughter in the front yard have dressed up for the portrait of their house. The wide porches with orn... Read more
The Cheshire Union and Company Store is a lively gathering place for residents of Cheshire as well as the surrounding rural district and the west side lakefront. When it was built in 1915, it was a different kind of gathering place - the Di... Read more
The home at 4258 Route 21 South, the corner of Goodale Road, was the Cheshire Post Office in the late 19th and early 20th century. A shop for dressmaking, sewing and hooked rugs, operated by other members of Postmaster Sibley Nott’s famil... Read more
The red building opposite Goodale Road is one of Cheshire's oldest commercial structures. It was built around 1880 by Cyrus Wilbur, a standout among Cheshire's 19th century entrepreneurs. This was one of several buildings Wilbur packed onto... Read more
The building group southwest of the Goodale Road intersection has always been the heart of Cheshire. The gable-fronted Cheshire Theatre and Meeting Hall, at the center of the group, was built in 1898 by the local chapter of the Knights of t... Read more
This elegant c. 1880 Italianate home at 4271 Route 21 South was built for John L. Johnson, a prosperous farmer and lifelong Cheshire resident.   Mr. Johnson appears in this 1898 view with his wife Caroline and son Clifford. By the time of... Read more
The two-story store building at 4272 Route 21 South predates the Meeting Hall next door and is among Cheshire's oldest commercial buildings. Probably built before 1870, it was the home of one of Cheshire's early businesses, S.R. Doolittle's... Read more
The Doolittle family was among Cheshire's early settlers, and this undated historic image, with the residents standing proudly in the front yard, illustrates the simple homesteads of these early residents. The fence in front and the shed in... Read more
The Community Church in Cheshire is the latest in a long tradition of religious institutions in and near the hamlet, beginning in 1796, when a Methodist Episcopal congregation was established in the vicinity of Route 21 and Nott Road. Nearb... Read more
James E. Chase relocated to Ontario County from the Schenectady region in 1839 at the age of 23, with a young wife and 75 cents. He attributed his successful rise from this starting point to three qualities - industry, sobriety, and religio... Read more
This mid-19th century homestead was built by James and Sarah Allen, whose descendants have been staunch Cheshire residents ever since. Mr. and Mrs. Allen take a proud position in front of their home in this undated photo. Lush greenery shad... Read more
Pine Bank Cemetery has been in existence for almost as long as Cheshire itself. The oldest part is at the rim of the gully, under the pine grove toward the rear of the cemetery, and the oldest reported stone is dated 1802. It was gradually ... Read more

 

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