A letter sent to Miss Lavinia W. Stowe in Pleasant Gap, postmarked from Chatham, Feb. 15, 1881. Courtesy of Gary Herndon, a descendant.

Growing up near Pleasant Gap, every day I passed through the quiet little community on the way to elementary school. One would think that the name is a descriptive one—a pleasant location to cross White Oak Mountain—but genealogy research has suggested the area was named in honor of the Pleasant family. Pleasant Gap was once its own little village with a selection of stores and a post office for over sixty years, but all of that happened over a century ago. The origins of the community lie with the arrival of the Walton family from Hanover County. 

The descendants of Revolutionary War  Lt. Jesse Walton (born around 1739) and former Miss Ann Pleasant (born around 1749) were among the early settlers of the area. Their son William Walton represented Pittsylvania County in the House of Delegates from 1808 to 1814 and again from 1822 to 1830. William married Miss Sallie Tanner and raised a handful of children on his property of over two thousand acres at Pleasant Gap.

The Waltons eventually established a store for their community and in March of 1840 a post office was established at the store about a mile south of White Oak Creek. The nearest post offices included Chestnut Grove (Whitmell), 6 miles to the northwest, Bachelor’s Hall, 10 miles to the southwest, Spring Garden, 10 miles to the east, and Pittsylvania Court House (Chatham), 11 miles to the northeast. Pete R. Bailey of Charlotte County, Virginia served as postmaster of Pleasant Gap for a couple months before William Walton’s son Thomas succeeded him in May of 1840. He served for over a decade as postmaster and can be recognized as one of the founders of the Pleasant Gap community. Thomas married Miss Nancy Washington Shelton, a granddaughter of early county settlers Daniel Shelton and Daniel Lanier. The 1850 census shows that another of William’s sons named Pleasant Walton worked as a school teacher. Also of note, a young county Sheriff named James Conway lived adjacent to Walton’s Store. 

The post office was discontinued a total of four times, the first instance being in 1850.  William Hutchings Harper reestablished the office in 1852 when he was a teenager. After three years, Thomas Walton reclaimed the responsibility. In all, there were fifteen different people who served as postmasters of Pleasant Gap until it closed in 1901. Here are a few highlights throughout the sixty-one year period. Thomas Walton’s son-in-law John W. Edwards succeeded him in 1856, followed by John James Pritchett Jr. (born 1824), whose nephew John Inge Pritchett served as postmaster of Whitmell for forty-six years. 

Three members of the Herndon family served Pleasant Gap in the 1870s and ‘80s. Doctor Aaron Herndon (born 1803; Doctor was his name) had previously established the post office at Chestnut Grove in 1830. Two of his sons Albert Sidney Herndon and Thomas Ford Herndon worked at Pleasant Gap and became successful tobacco farmers.

Some of the other community residents who owned businesses included brothers William A. Owen and James H. Owen, William R. Rogers, and John H. “Hutch” Harper (son of the abovementioned William Harper). Like the fate of many other small farmer’s post offices, it closed in October 1901 in anticipation of the upcoming Rural Free Delivery (RFD) program that was implemented the following year. The last postmaster of Pleasant Gap, Hutch Harper, was involved with the country store business over a period of about forty years and continued long after the discontinuation of the post office until his death in 1933. A few businesses survived into recent years, but now Pleasant Gap remains mostly as a quiet back road along the mountain with little indication of its long history.