Touring the Backroads...

Tour 2 -- Charles Town to Shepherdstown, via Harpers Ferry
John Brown’s body, Civil War destruction, a view “worth a voyage across the Atlantic,” and a very early steamboat

This tour begins north of Winchester, off I-81. It’s about an hour’s drive west from the Washington, DC, Beltway, and about three hours from Philadelphia or Richmond. It makes for a perfect weekend getaway any time of year. If you have an interest in George Washington’s family, you’ll be able to drive by several old homes, still privately owned, that were built by his brothers or grand nephews. Civil War buffs will enjoy visiting Harpers Ferry National Historical Park, as well as the courthouse in Charles Town where John Brown was tried and the yard where he was hanged. Shepherdstown’s Colonial-era architecture and its location above the Potomac River, not to mention its shops and restaurants, make it a favorite destination of DC-area daytrippers.

The first stop is Charles Town, after you drive past three 1800s-era Washington family homes in the nearby countryside. Best known today for its racetrack, Charles Town was the scene in 1859 of the treason trial of John Brown. It is also where George Washington’s brother Charles built the first structure of his home, Happy Retreat, around 1780; efforts are underway to open this house to the public.

The next stop is the historic “re-created” town of Harpers Ferry, at the confluence of the Shenandoah and Potomac rivers. When Thomas Jefferson passed through here in 1783, he climbed up a hill above the town and later wrote that the view “was worth a voyage across the Atlantic.” The National Park Service operates a national historical park here, with daily programs and exhibits. The Schoolhouse Ridge Battlefield was the scene of General Stonewall Jackson’s first attempt at invading the North; he captured 12,500 Union soldiers here in 1861.

The last stop is Shepherdstown, possibly the oldest town in the Shenandoah Valley. Just a mile east of town, the Valley’s first group of settlers from Pennsylvania entered the Valley by crossing the Potomac River at a shallow spot. Many lovely old stone buildings and homes line the main street of this charming town. In 1790, Shepherdstown was on President Washington’s list of proposed sites for a new U.S. Capital—after all, it was the geographic center of the new nation at the time.


Touring the Shenandoah Valley BackroadsTo learn more about the Shenandoah Valley’s history and its scenic backroads, and for detailed driving directions and more in-depth information for the tours on this website, get a copy of Touring the Shenandoah Valley Backroads (2nd ed., 2010; ISBN 978-0-89587-3-866; $19.95) by Andrea Sutcliffe.

It’s available through your favorite bookseller (go to to find an independent bookstore near you), at many Shenandoah Valley gift shops and museum stores, or directly from the publisher, John F. Blair, 1-800-222-9796.

Original text and photographs for the tour descriptions on this website © 2012 by Andrea Sutcliffe

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