If you’ve ever walked through downtown Leesburg and wondered what it might’ve looked like during the days of tricorn hats and revolution, now’s your chance to find out.
Local historian and longtime Loudoun educator Rich Gillespie will be leading a special walking tour on Saturday, November 1 at 10 a.m., diving into Leesburg’s role in the American Revolution. The tour, titled “Leesburg, Loudoun and the American Revolution,” brings Loudoun’s colonial history to life, right where it happened.
Loudoun in the 1770s: Not Quite Virginia, Not Quite Pennsylvania
Back in the 1770s, Loudoun County was still a new kid on the block—created in 1757 by the House of Burgesses—and looked very different from the suburban sprawl we know today. As Gillespie explains it, this part of Virginia was considered part of the “Southern Back Country,” more culturally connected to Pennsylvania than the Tidewater elite. That tension between backcountry grit and colonial power centers set the stage for how local people experienced the growing push for independence.
“This is a chance to see how the Revolution wasn’t just something that happened far off in Boston or Philadelphia—it had meaning right here,” Gillespie said.
The tour will begin at the Thomas Balch Library parking lot, and from there, participants will explore a number of significant Revolutionary-era sites still visible in downtown Leesburg. Along the way, Gillespie will offer insight into how the events of the Revolution rippled through Loudoun—and how they helped shape what came after.
Just 50 Spots—And They’ll Go Fast
The walking tour runs for about two hours, and it’s outdoors the whole time, so good walking shoes, layers, and water are a must. Participation is limited to 50 people, and pre-registration is required. You can reserve a spot by calling 703-737-7195, emailing balchlib@leesburgva.gov, or registering online.
If you can’t make it this fall, don’t worry—the tour will return in spring 2026.
Who’s Leading?
If you’ve spent any time learning about Loudoun’s past, chances are you’ve come across Rich Gillespie. A former Loudoun County teacher and Historian Emeritus of the Virginia Piedmont Heritage Area Association, Gillespie has spent decades connecting locals to the rich, complex history just beneath our feet. His tours are known for being informative, personal, and full of little moments that make the past feel alive
