Pittsford for generations has been known among Western New York communities for a special quality which combines charm, country elegance, pride, and a sense of individuality. Perhaps this is due to the fact that it was the first settlement east of the Genesee in what is now Monroe County and has played a pivotal role in development of this area. In any case, right down to the present time it has maintained much of the grace and spirited independence so characteristic of the days of the early Republic. It also has retained a physical identity unique among Monroe County communities.

At the Four Corners area, major business structures date from about 1814, 1826, and 1886. Other old-time business structures have survived on South Main Street. The Monroe Avenue area is one of the finest groupings of old homes in Western New York. Elsewhere in the Village are at least 100 buildings of note, survivors from earlier periods. There is a like number in the Town of Pittsford outside the Village limits. Of special note is the little group of structures around the old Pioneer Cemetery, one mile south of the Four Corners. Existing here is an 1857 schoolhouse and the Lusk Homestead, dating from about 1814. This Federal style farmhouse is the focus of a designated "Century Farm," operated by the same family for over 100 years.

In the Phoenix Building and the Hargous mansion, now St. Louis Church Manse, Pittsford has what architectural historian Paul Malo has called two of the genuine New York State monuments of the early nineteenth century. These and other buildings will be seen on your walking tour, made easy with a map developed by Historic Pittsford, Inc., an organization devoted to the preservation of the charm and historic buildings of Pittsford.

The Pittsford area was known to white men long before the arrival of the first permanent settlers in 1789. It was crisscrossed by major Indian trails. Its fertile land made it the site of Indian villages. It was first noted into history in 1687, when the Marquis De Denonville, leading a French army on a punitive expedition against the Seneca Indians, camped in what is now the vicinity of State Street and South Street at what then was known as "Big Spring".

The Buffalo Creek Indian Treaty of 1788 opened the area for settlement. The next summer saw the arrival of Simon and Israel Stone, Washington County residents, who built their homes in the vacinity of the "Big Spring", now believed to be a portion of Israel Stone's home preserved as part of the building at 38 State Street.

The town first was called Northfield. In 1808, to avoid confusion with another Northfield, the name was changed to Boyle. In 1813, a further change was made to Smallwood. Caleb Hopkins, a Colonel in the War of 1812, divided the town into Brighton and Pittsford, naming the latter after his own former home, Pittsford, Vermont, a year later.

Much of the early activity in Pittsford was farming but early residents also made use of abundant sand, gravel, and limestone, supplying these to a considerable area. Nearby Irondequoit Creek provided power for a grist mill built by Simon Stone in 1791. Two years later Stone built a saw mill.

Pittsford became almost instantaneously a highly prosperous community. The fine quality of many buildings surviving from that early period boasts of the community's first school (built in 1794), library (formed in 1803), and post office (established in 1811). It was the home of the first lawyer. The Village of Pittsford was also honored to have the first doctor to practice in Monroe County.

The construction of the Erie Canal, built in 1817-1825, had a satisfactory effect on Pittsford's economy. The Canal triggered the phenomenal growth of the Village of Rochesterville and in 1834 became known as the City of Rochester. The astonishing growth of the community at the falls of the Genesee River quickly stole the spotlight from Pittsford. This circumstance seems to have troubled the equanimity of Pittsford very little, which continued for more than 100 years as the center of a prosperous farming area. It also preserved the settled, patrician air which made it different from other area farm towns. Families of substance had lived in Pittsford from the earliest days and they continued to do so. Small industries sprang up - distilling, gun powder manufacture, and the production of malt being among them. They prospered modestly but never on a scale to rival with what was happening in Rochester.

In the late nineteenth century wealthy rochesterians established country estates in and around the Village. As the 20th century wore on, tracts of smaller homes made their appearance in areas surrounding the Village. The full flood of suburban development did not occur until the 1950's. By 1957, the population had climbed to 13,476. By 1983, that number had risen to 22,620, including 1,568 Village residents. There has been commercial development on Monroe Avenue, notably Pittsford Plaza, and several multiple housing units have been constructed, but most of the recent development has been individual quality housing.

The preservation movement, spearheaded by Historic Pittsford, has helped raise the community's awareness of the richness of Pittsford's heritage. During the midst of growth, Pittsford has retained the charm of an early 19th century community.