The area of today's Grahamsville had initially been settled during the colonial era, but raids by Loyalists and their Indian allies killed or drove them away during the Revolution. So, after independence, the landowners of the Hardenbergh Patent invited tenants to settle in the area, named after an officer who led a unit massacred in the area, once again. The first known house in Grahamsville dates to 1788. The minimal farming opportunities in the region were supplemented by lumber, which the Catskills had in abundance, and soon that business picked up. In 1813 the town of Neversink raised taxes to build a road from the Neversink River to more-established routes at Wawarsing in Ulster County, to the east. The Marenius Dayton House, an impressive Greek Revival building in the district, was an inn and official stagecoach stop during this era Lumbering gave way to tanning, as the Catskills' vast Eastern hemlock stands had plenty of tannin in their bark. Judge Stoddard Hammond became rich through this industry, building a tannery complex along nearby Chestnut Creek and a Gothic Revival cottage overlooking it in 1857. Like many Catskill tanners, he did extremely well during the Civil War, supplying the Union Army with all its leather. He sold the tannery and its associated properties, including a Greek Revival company store that still survives, to his partner John ReynoldsNew York Cityafter the war. Reynolds kept the tannery going, even after the Panic of 1873, and the citizens of Grahamsville were able to build their church, meeting house and cemetery at the east end of the district the following year. But in 1878 he finally closed it, and the hamlet's tanning days were ended. With the pollution from the tanneries gone, Sullivan County became a summer resort destination in the late 19th century. The Italian villa-style Southwick House, dating to 1882, is representative of this period. That business either faded or shifted southwards after the 1920s, and Grahamsville reverted to its farming and lumbering days. The center of the hamlet is now to the west of the district, near the junction of routes 42 and 55, in the wake of the construction of Tri-Valley Central School and Rondout Reservoir to the east. The buildings from Grahamsville's early years are still mostly intact.
