Italianate House
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 ornamental brackets at the columns, the wide eaves and the hipped roof with central cupola are all features of the Italianate style. See Photo #2 for a contemporary view.
Cheshire School
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 District #5 School. The four-room "modern" schoolhouse replaced four rural one-room schoolhouses within a few miles of Cheshire. It served grades one through eight. The school's modern conveniences included indoor bathrooms, a woodworking shop, and school bus service. In the winters of the 1940s, children were invited to bring a potato to school and carve their initials in the potato. The potatoes were baked through the morning and eaten at lunch time.When Canandaigua consolidated its rural schools in 1954 and built the central Elementary School, the Cheshire School became obsolete. It was vacant for about 20 years until John and Barb Rose purchased it to move and expand their grocery business, the Company Store, at the lower level. The four upper level classrooms have housed a host of small businesses since then - antiques and gift shops, art galleries, wines and spirits, and others. The original wood floors and trim, tin ceilings and cloakrooms remain intact.
Old Post Office
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 family, shared the building. Before rural delivery, area residents had to visit the post office to get their mail. A long porch with comfortable rocking chairs made this a fine spot to gather and hear the news of the day.
Wilbur's Hotel and Violas Store
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 the site, where he operated a hotel and tavern, a grocery store, and a farm commodities brokerage business. In addition, when the current Cheshire Community Church was built in 1870, he bought the old church and had it moved to the site for a meeting and entertainment hall, renamed Lincoln Hall after the fallen president. In the middle decades of the 20th century, C.P. and Adeline Violas ran an IGA store and Texaco station from the existing building and a neighboring one.
Cheshire Theatre and Meeting Hall, formerly Maccabee Hall and Cheshire Grange
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 the Maccabees, a fraternal organization for rural families. In the 1920s, the Cheshire Grange assumed ownership. Under both groups, the hall was the center of Cheshire's social life and formal events. When the school had an event for the whole student body, such as an assembly or graduation ceremony, the Grange was used. It was the starting point for Cheshire parades, such as those in the historic views. The building hosted minstrel shows, concerts and plays, produced by the Cheshire Amusement Company. It was listed on the National and State Registers of Historic Places in 2013 as a well-preserved example of a rural fraternal lodge hall. The interior features its original bead board walls and ceilings, a stage, and a c. 1940 custom-painted fabric stage backdrop featuring advertisements for local businesses. The current owner, Cheshire Community Action Team, plans to reopen the building for community entertainment, education and cultural programs.
Johnson House
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 the 1977 view it has taken on a different look, with a contrasting color scheme. The hipped roof, wide eaves, and double projecting bay are all surviving Italianate features, though the rooftop cupola and iron cresting have been removed. Note the wooden sidewalks in the 1898 view and the field stone curbing in the 1977 image.
Stinardo Store
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 Boots and Shoes. The pre-1898 image shows multiple product lines - men’s hats. barbed wire, and hardware being sold alongside the footwear. The Mallory family ran a general store including gasoline sales at the property from the 1920s into the 1950s, operating under the Red and White and then the Leadway chains. The Stinardo family took over from the Mallorys, and in the 1970s this was the original home of the Company Store. Since then a host of small businesses have operated out of this property - gift shop, antiques, a liquor store, a meat market, and others.
Doolittle Home
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 the rear are a reminder that most 19th century Cheshire residents were farmers, working lands behind their homes and sometimes also leasing land at a distance. Mark Doolittle came to Cheshire from Connecticut in 1814, liked what he saw, and returned the following year with his family of 15 in a prairie schooner. The Doolittles settled up and down Main Street, including Lyman W. Doolittle and his family, who lived in this home around the turn of the 20th century. The industrious Doolittle family included farmers, harness makers, a tax collector, and the dealer in boots and shoes up the street.
Cheshire Community Church
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. Nearby congregations of the Baptist and Christian denominations followed in Cheshire and Academy, and in 1840 the First Freewill Baptist Church of Canandaigua built the first church in Cheshire on this site, sharing the structure with the Methodist and the Christian denominations. The current church building was built in 1870, and continued to be shared by multiple congregations for decades. Eventually the various Cheshire churches opted to merge into a single entity called the Union Church of Cheshire. This early image was taken before the construction of the front porch, and before the 1910 addition of stained glass windows.
Chase House
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 religion (W.H. McIntosh, History of Ontario County, 1876, p. 126). The new home he built in Cheshire in the 1870s was among those featured in the 1876 County History, and included the finest Italianate features - a tower with a patterned slate roof (later removed), a matching barn with cupola, hooded window crowns, and a well-landscaped lawn separated from the street by a fence and gate. In addition to the home he acquired "a farm of two hundred acres of good land free of encumbrances." In the mid-20th century, the home was occupied by C.P. and Adeline Violas, proprietors of the store at Tour Stop 3.
James and Sarah Allen House
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 shades the home's entry porch, then and now.
Pine Bank Cemetery
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 enlarged through the 19th century, and around 1902 it was turned over to a private cemetery association. Along with many generations of Cheshire families, Pine Bank is the resting place for 114 veterans of war, including two veterans of the American Revolution, two from the War of 1812, one from the Mexican War, 34 from the Civil War, 14 from World War I, 45 from World War II, five from the Korean War and 11 from the Vietnam War. In addition another ten Cheshire residents lost their lives in the Civil War but were buried elsewhere; a memorial to them has been placed at Pine Bank.For more information about Pine Bank and the other tour sites, see A Walking Tour & History of the Hamlet of Cheshire, by Town Historian Ray Henry, available at the Company Store or the Wood Library.
