Pleasantville, located along West Pithole Creek, was settled by Aaron Benedict soon after he came west to build a portion of the Susquehanna and Waterford Turnpike. In 1819, he purchased from the Holland Land Company a large portion of the land now called Pleasantville. With his son-in-law, William Porter, a potter, Benedict mined the nearby clay deposits and began producing Rockingham and Liverpool Queensware with the help of imported Scots-Irish labor. Their pottery company operated from 1825 until the early 1880s. The addition of a smithy and a tannery brought nearby settlers to the area originally named Benedictown and Holland, after the earlier owners. Benedict's nineteen children helped to swell the population. In 1849, a borough one mile square was chartered with the name Pleasantville.
After oil was discovered at the Harmonial Well No. 1 in 1868, the borough's population tripled within two months. Rail service began and roads were improved to accommodate the new industry and population. The wells continued to produce at a greatly reduced rate into the twentieth century, until the introduction of secondary recovery methods (for example, floating well-bottom oil to the surface by flooding the wells with water) brought the oil industry a brief resurgence in 1926.
The white, frame Pleasantville Free Methodist Church (N. Main and Merrick streets) was built in 1847–1848 by Aaron Benedict for the Baptist denomination. Its Greek Revival styling and serene simplicity tie it stylistically to Benedict's New England roots. There were several fine examples of this style in the area, such as the Congregational Church in Riceville and the Independent Congregational Church in Meadville (both demolished). The Pleasantville Church has three bays below the pedimented gable end, and a square bell tower with a small spire is centered above the pediment.
One Greek Revival house (c. 1840; 353 Main Street) is similar in character to a group of houses also built in the 1840s in the 1200 block of Elk Street in Franklin ( VE8). It was built by Aaron Benedict's nephew, E. R. Beebe, who came to Benedictown in 1831 to found a tannery and shoe business. With its central pavilion and single-story flanking wings, wide cornice, returning eaves, and simple corner boards, this is an excellent example of the style. Two houses on Chestnut Street at numbers 317 and 341, and houses at 121 State Street and 248 N. Main Street all date from the early 1870s and were built soon after a major fire damaged much of the town, while oil fever continued in Pleasantville. The Colonial Revival house at 345 Chestnut Street built in 1906 illustrates that Pleasantville's healthy prosperity continued into the early twentieth century.
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