"Although there were mills and houses in the Gap in the late 1700s, the town of Hillsboro (spelled Hillsborough until its 1880 incorporation) was not formally established until December 31, 1802 by an act passed by the Virginia General Assembly. The trustees of Hillsboro named in the act were Mahlon Hough, Samuel Purcell, Jr., Thomas Leslie, Josiah White, Jr., Edward Cunard, Mahlon Roach, and Thomas D. Stevens. By June 20, 1811, when Henry Griffin bought lot No. 12 on the town plat at auction for $88.50 paid to the trustees, he was required to build "a House thereon Twelve feet Square or equal thereto with a Stone or Brick Chimney to the same and a Shingle Roof on it within Four years of the Day of the Sale of the said lott." Due to its favorable location on the Vestal's Gap Road, the town grew quickly and in the early 1800s was one of the leading trade centers of western Loudoun, along with Snickerville (Bluemont) and Woodgrove, which has since disappeared. Much of Hillsboro's activity was due to its mills, with as many as five operating at one time, all on Catoctin Creek or its nearby branches."
A row of nineteenth century houses in Hillsboro
During this period there typically were three or four doctors in town, five or six general stores, a large tanyard and cooper shop, two shoemakers and three taverns. Two blacksmiths, two saddle and harness makers, two wagon makers and a livery stable tended to the needs found in the horsepowered era. Seamstresses and tailors made clothes from the yarn goods produced by the Gaver woolen mill.
However the newly constructed railroads and turnpikes bypassed Hillsboro, drawing trade and commerce away from the town. The Civil War events, including the Burning Raid of 1864, devastated the area. During the post-Civil War period, Hillsboro began its transformation from a busy commercial center to a primarily residential community. Homes formerly housing taverns, shops and stores gradually became residences. With the turn of the 20th century, virtually all of the currently existing structures within the town had been built and little has been altered in the majority of the structures since then.
Until 2000 there were no street addresses for the buildings in town; the 60-odd buildings in Hillsboro were referred to by their owners' names or their purposes.
Old Stone School in Hillsboro
A central feature of the town is its affectionately named "Old Stone School." Originally named Locust Grove Academy, the oldest part of the building, the east wing, was built in 1874. The Academy's first principal was Mrs. J.B. White. The Old Stone School, as it is referred to now, is situated astride the eastern entrance to the town on Route 9. The stone structure was completed in 1917 with the addition of more rooms on the west side. A junior high school was established there in 1918, and operated for 17 years, until 1935. The brick auditorium was added in 1929. Classes for Grades One through Seven were taught there until the spring of 1966, when Hillsboro Elementary opened. The school was the hub of the community in the early 1900s. Community plays were frequently held there with a local orchestra that played during intermission.
Located next to the Old Stone School is Hillsboro Charter Academy, which opened in 2016 inside the former Hillsboro Elementary