Pittsford, an eastern suburb of Rochester, carries a rich history that dates back over two centuries, with a legacy that began even before its current name took root. This town evolved through several iterations, shaped by pioneering settlers who ventured into the wilderness following the Revolutionary War. From dense forests to a thriving community, Pittsford’s journey reflects the determination and vision of early American settlers who transformed untamed land into a place they could proudly call home.
The Origins of Northfield: Discover the initial settlement of the area by Israel and Simon Stone in 1789, describing the territory’s geography as part of the Phelps and Gorham Purchase, and how the cousins established “Stonetown” after the Revolutionary War.
In 1789, cousins Israel and Simon Stone acquired approximately 13,000 acres of densely forested land in what would become Pittsford. This territory was part of the Phelps and Gorham Purchase, a vast two-million-acre tract stretching from the Pennsylvania border to Lake Ontario, with Seneca Lake forming its eastern boundary and the Genesee River its western edge. The Stones, Revolutionary War veterans, likely spotted this fertile region during Sullivan’s campaign against the Iroquois. Despite being called “Northfield,” the area was hardly open fields but rather thick woodland requiring considerable labor to clear for settlement.
After purchasing the land, the industrious cousins immediately established a foothold by constructing two log cabins. Israel built near “The Big Spring,” a former Native American camping ground (near today’s 38 State Street), while Simon settled a short distance south. They then journeyed back to their hometown of Salem in Washington County to recruit additional settlers. Their persuasive abilities must have been remarkable, as they returned with their families and about eight others. This small community, primarily consisting of interrelated families with surnames like Stone, Nye, Dunn, and Dodge, formed the nucleus of what locals called “Stonetown” – the foundation of present-day Pittsford.
Early Town Development and Governance: Outline the formation of the first town government in 1796, the establishment of Northfield, and how the growing population led to the creation of surrounding towns from the original territory.
By 1796, the population of the Northfield territory had grown substantially enough to warrant formal governance. On April 5th of that year, settlers gathered at Paul Richardson’s home in what is now Pittsford Village for the first official town meeting. Dr. John Ray, Northfield’s pioneer physician, served as town clerk and meticulously documented these early proceedings in handwritten records that survive to this day. This original Northfield was extensive, encompassing what would eventually become seven distinct towns: Pittsford, Perinton, Penfield, Brighton, Webster, Irondequoit, and Henrietta – a testament to the scale of the Stone cousins’ original land acquisition.
As more settlers arrived in the fertile Genesee Valley throughout the late 1790s and early 1800s, the expansive territory of Northfield became difficult to govern as a single unit. In 1803, the town changed its name to Boyle, partly due to confusion with other New York communities named Northfield. The process of subdivision began in 1810 when Penfield separated from the main territory, followed by Perinton in 1812. After these divisions, the remaining community was briefly known as Smallwood. This pattern continued with Brighton’s formation in 1814, Henrietta in 1818, and later Irondequoit (1839) and Webster (1840) – all carved from what was once the vast Northfield territory.
Caleb Hopkins’ Influence: Highlight the arrival and rise of Caleb Hopkins, from his settlement near Indian Landing to his military career during the War of 1812, and his emergence as a prominent town leader.
In 1789, nineteen-year-old Caleb Hopkins arrived in the region, initially settling near Indian Landing on Irondequoit Bay in what would later become Penfield. His American lineage ran deep – his great-great-great grandfather had been a Mayflower passenger. The ambitious young man built a log cabin and married Dorethea Mabee, daughter of his longtime friend Jacobus Mabee. By the turn of the century, Hopkins and his wife relocated south of Northfield (later Boyle), where he began establishing himself as a community leader and military man.
Hopkins’ military career flourished alongside his civic engagement. In 1804, Governor Clinton commissioned him as a militia lieutenant, and by 1807, Governor Morgan Lewis promoted him to major. In 1808, he was appointed Supervisor of Boyle to fill an unexpired term, winning election to the position the following year. President Madison further recognized his capabilities by appointing him as United States Inspector of Customs and Collector of the Port on the Genesee River. His military prominence grew during the War of 1812, where he served at the Niagara Frontier under General William Wadsworth, fighting in several battles and earning a reputation for bravery despite suffering shoulder wounds. By April 1813, Governor Tompkins commissioned him Colonel of the 52nd Regiment of Militia, cementing his status as the area’s leading citizen.
The Naming of Pittsford: Chronicle the town’s name changes from Northfield to Boyle to Smallwood, culminating in how Colonel Hopkins was given the honor of naming the town Pittsford in 1814 after his Vermont hometown.
The settlement’s identity evolved through several name changes before finding its permanent designation. Originally established as Northfield in 1789, the town changed its name to Boyle in 1803, reportedly due to confusion with other Northfields across New York State. As portions of the territory separated to form Penfield (1810) and Perinton (1812), the remaining community became known as Smallwood. These transitions reflected both the practical challenges of governing an expanding population and the emerging distinct identities of the various settlements within the original territory.
On March 21, 1814, when the town was divided yet again with one section becoming Brighton, residents honored their most distinguished citizen by allowing him to name the remaining portion. Colonel Caleb Hopkins, respected for his military service defending the Port of Charlotte against British forces and his leadership in local government, chose “Pittsford” after his childhood hometown in Vermont. The following year, Hopkins received a promotion to Brigadier General for his gallant service in the War of 1812. Though his life was relatively brief – he died in 1818 at just 47 years old – his legacy endures through the town’s name and his family’s continued presence. His descendants maintained the family homestead at 3151 Clover Street for generations, and both he and his wife Dorothea rest in the Pioneer Burying Ground on South Main Street, having left a lasting mark on the community that continues to honor his memory today.
