I haven't posted here in awhile but I do have more recent research. I few recent emails have got me digging again. Since a good portion of my family seems to have stayed in western New York for a good number of generations it behooves me to understand the dynamics of the changing city and county names.
I've drawn up this basic timeline for Pittsford/Monroe.
1788 Oliver Phelps and Nathaiel Gorham of Connecticut signed Treaty of Buffalo Creek with Seneca Indians
1789 Simon and Israel Stone from Salem Washington Co. NY settled here (went back to bring friends and family)
1792 District of Northfield, Ontario Co. created from 7 townships
1794 School built in Mendon (school structures called Stonetown then The Milepost)
1796 Town of Northfield created (Silas Nye, first supervisor and Dr. john Ray was town clerk)
1808 Northfield was divided and became Boyle
1813 More divisions and renamed Smallwood
1813 Town of Mendon was organized in Ontario County
1814 Smallwood was divided into Henrietta and Pittsford (P. was named by Col. Caleb Hopkins)
1821 Mendon annexed by Monroe County when created
Here is a good short history sourced from here:
The earliest history we have of our area is that it was part of the lands of the Seneca Indians, the western most tribe of the mighty Iroquois nation. We have records that show that the Marquis DeNonville crossed Lake Ontario from Montreal in 1687 with a force of two thousand French and Indian warriors to make war on the Senecas. DeNonville landed at what is now Ellison Park on July 10, and marched overland, following roughly the path of Irondequoit Creek. That army camped at the Big Spring, a favorite camping site of the Native Americans. DeNonville and his punitive forces were successful in driving the Senecas from this region but in so doing he created a powerful ally of the English against the French. Whenever there was conflict between the two nations, the Senecas sided with the British.
In 1788 Oliver Phelps and Nathaniel Gorham of Connecticut settled with the state of Massachusetts for a title to the land in western New York. On July 8, 1788, Phelps and Gorham met with the Senecas and signed the Treaty of Buffalo Creek at Geneseo in Livingston County at which the Indians gave up title to all the land between the Genesee River on the west and Seneca Lake on the east and from Lake Ontario south to the Pennsylvania line. This comprised about two and one-half million acres, Simon and Israel Stone, two cousins from Salem, New York, Washington County, had been officers in the Revolutionary War. They had heard about this fertile land in western New York state and arranged to purchase 13,296 acres of land, land for which they were to pay about 36 cents an acre. The two men came to this area in the year 1789 and built crude log cabins. Israel established his site at the Big Spring and Simon's was just a short distance to the south. The two cousins then went back to Salem and were able to persuade family members and friends to join them in this new venture in the "west".
In 1792 the seven townships northeast of the Genesee River were organized into the District of Northfield as part of Ontario County. That same year, Simon built a grist mail on Irondequoit Creek. He built a sawmill the following year and frame houses soon appeared, giving the new community a more permanent look.
The early settlers were proud of this Northfield and wanted to be sure that it grew and developed into a thriving community. A school house was built in 1794 in the area where Mendon, Mendon Center, and Stone Roads merge.
This settlement of structures was called Stonetown but later was known as The Milepost. The cost of this school, the first in what is now all of Monroe County, was raised by subscription with each family paying in proportion to the number of children who would be attending. That cost was $ 1.00 per student.
On April 5, 1796 the District of Northfield was organized as the Town of Northfield. A full set of town officers were elected at that first town meeting held in what is now Pittsford village. Captain Silas Nye was elected the first supervisor and Dr. John Ray was chosen to be Town Clerk - a position he held for the next sixteen years.
In 1808 the town was divided and the name Northfield was changed to Boyle. In 1813 there were more divisions and the name Smallwood was given to this area. In 1814 Smallwood was divided and one part was called Henrietta and the remaining part was named Pittsford. That name was chosen by Col. Caleb Hopkins, a leading citizen who had been supervisor and a hero of the War of 1812. Hopkins named this town for his hometown of Pittsford, Vermont.
A great event in the life of our community was the opening of the Erie Canal in 1825. The village soon become a busy shipping port with produce being sent to the eastern markets. It also brought a heavy migration of settlers from New England and land values rose rapidly. The village expanded and was incorporated in 1827. Another important event which contributed to growth was the coming of the Auburn and Rochester railroad in 1842.
Prior to the Civil War, there had been stories of runaway slaves being hidden in homes and cellars - all part of the Underground Railroad. Unfortunately, we have very little documentation of this theory. We do know that Samuel Crump, a merchant whose store was at the Four Corners, is known to have received runaways into hiding in his barn and in turn, took them in his wagons to the Port of Charlotte where they boarded a boat for freedom in Canada.
There are also, rumors of underground caverns and tunnels beneath the streets of Pittsford village. We have the accounting of more than one person who says they have been in those tunnels, but no one alive today is able to corroborate this fact. If there are caverns and tunnels underground, there is no evidence of any connection with Underground Railroad trafficking.
Pittsford was established as an agrarian community by people of common stock who were willing to let commercialism pass them by. Industry was not encouraged, although there was at one time a thriving Pickle Factory in the community and Pittsford Milling Company was a flourishing business through World War II. The town today is primarily residential and serves as the "bedroom community" for the city of Rochester which is only about ten miles away. Pittsford is an area of beautiful homes and gardens, trees and historical buildings. The school has an excellent reputation as does the library. The municipal officers of both the town and village have paid particular attention to parks and recreational opportunities and have collaborated on many community events. There are numerous restaurants, shops, boutiques and places of worship. In a word, Pittsford is an ideal community in which to live and is ideally located in beautiful upstate New York.