The town of Fincastle was originally settled by Scotch-Irish and German immigrants from Pennsylvania who arrived in the region in the mid-18th century.

John Miller erected a sawmill which became the nucleus of the early village of Fincastle.

Two years later, Israel Christian donated 45 acres (18 ha) of land and laid out the streets and lots for the new town of Fincastle.

Around the same time, a brick church was constructed on land donated by Israel Christian to serve as the established (Anglican) house of worship for the town.

[7] By the early-19th century, the village had grown into an important regional center of commerce, especially for the wool industry, aided by the construction of taverns, hotels, and shops.

A second courthouse was erected in 1818 and replaced by a third, a larger brick structure of Greek Revival style in 1850.

This courthouse continues to serve Botetourt County today, having been rebuilt after a disastrous fire in 1970.

The Bowyer-Holladay House, Breckinridge Mill, Fincastle Historic District, Greenfield, Hawthorne Hall, Prospect Hill, Santillane, Wheatland Manor, and Wiloma are listed on the National Register of Historic Places.

[1] The United States Postal Service operates the Fincastle Post Office within the town.

The center is operated by Virginia Western Community College and provides career studies certificates in welding, commercial HVAC, and healthcare programs.