Hiking, cycling and horse riding are all popular pursuits for Loudoun’s more adventurous outdoor enthusiasts, but what if you want a less strenuous, more informational journey?


Here are five, self-guided tours that will stretch the mind – and sometimes the legs.

Leesburg Walking Tour App

Go to Loudoun.gov and download the Leesburg Walking Tour App. There are multiple walking tours of the town to choose from including Highlights of Historical Leesburg, which features 11 sites including George C. Marshall’s Dodona Manor, and an African American History Tour, taking you to the African American churches, cemeteries and schools of downtown Leesburg, as well as to the homes of prominent black figures such as Reverend William Robey on North Street, founder of one the first Freedmen Bureau school in town.


Downtown streetscape of Leesburg Virginia


The Appalachian Trail

Make your way to Bear’s Den off Route 7 in the Blue Ridge Mountains above Bluemont and hike the short but strenuous Loudoun stretch of the Appalachian Trail – known as Virginia’s Rollercoaster. Bear’s Den has spectacular views of the Shenandoah Valley to the west, pine trees all around. On the other side of Route 7, above Round Hill, the trail leads you down the mountain along a set of stones that form a natural staircase leading to the Blackburn Trail Center log cabins. A rustic 1910-built lodge, it’s a refreshment station for hikers and available for rent outside of peak season.


Bears Den Overlook


Waterford’s Walk with Us.

Download (or pick up a copy of) the Waterford Foundation’s “Walk with Us…” pocket guide and learn about the astonishing history of this picture-perfect 1733 Quaker town and National Historic Landmark. While the booklet offers no set route, you can walk the narrow streets and read – with accompanying pictures – about more than 100 of the town’s structures, including everything from still-standing circa 1733 Janney’s Mill on Catoctin Creek to the town’s churches, log cabins, Second Street School and immaculately preserved Colonial, Federal and Victorian homes. When tired, pop in for a soda at Linda’s store, the town’s only grocery, where the owner’s sheep frolic in muddy fields behind the coke machine.


waterford mill


Virginia Civil War Trails

Marked by the distinctive red bugle on its road signs and guidebooks, the Civil War Trails heritage project connects visitors with the great campaigns, lesser-known sites and famous personalities of the Civil War. In Loudoun, follow the trail to the site of 1861’s Battle of Balls Bluff, now a National Historic Landmark and cemetery, to the 1863 Battle of Middleburg on Route 50 (waged during Gettysburg), and to Gleedsville, on Route 15, where a plaque commemorates Martin van Buren Buchanan, a black soldier in the Union’s 2nd United States Colored Troops regiment who founded this African American settlement near Oatlands in 1890.


balls bluff 



Virginia Piedmont Heritage Area Driving Tours

Drive the byways and backroads of Loudoun to follow the path used by Civil War soldiers 150 years ago. Founded in 1995 to preserve the rural historic landscapes of Loudoun and other Virginia Piedmont counties, The Virginia Piedmont Heritage Area highlights three self-guided driving tour brochures for Loudoun including the “Old Carolina Road” (Route 15),and “Quaker Sites”, the latter exploring the abolitionist Quaker towns of Waterford and Goose Creek (Lincoln).


Lincoln Store