Touring the Backroads...

Tour 3 -- Middletown to Winchester
Log, limestone, and brick—a microcosm of early Valley architecture

This tour begins just an hour’s drive west of the Washington, DC, metro area; it’s about two hours south of Harrisburg, PA. As you drive along this 16-mile stretch of the Valley Pike (U.S. 11), you will see a few of the Shenandoah Valley’s oldest homes as well as a major Civil War battlefield. Most of this tour is spent walking around charming Old Town Winchester, where George Washington’s military and political career began when he was just in his early twenties. History buffs should set aside half a day to visit the Museum of the Shenandoah Valley while here.

About a mile south of Middletown, be sure to stop and tour Belle Grove, a beautiful old (1797) limestone manor house that is a long-time National Trust Historic Site. It is now part of the Cedar Creek and Bell Grove National Historic Park. Its builder was the grandson of one of the Valley’s early pioneers, Jost Hite. It sits adjacent to the Cedar Creek Battlefield, where the Union Army’s victory here in 1864 helped ensure President Lincoln’s reelection three weeks later. Interestingly, two future U.S. presidents fought in that battle: Rutherford B. Hayes and William McKinley.

Middletown itself boasts the Wayside Inn, which has been serving travelers for more than 200 years. It gracefully made the switch from stagecoach inn to roadside lodging in the early 1900s and calls itself “America’s First Motor Inn.”

About one mile north of Stephens City—once home to more than a dozen businesses making Conestoga-type wagons—is another old limestone mansion, Springdale. The land this 1753 house sits on, as well as that of the old mill across the street, first belonged to Valley pioneer Jost Hite in the 1730s. Legend has it that Hite’s friend George Washington used to visit him here. That’s quite possible, since Washington was a teenage surveyor for Lord Fairfax in this neck of the woods and later a Winchester resident.

Winchester today is a bustling small city, but when George Washington arrived here in 1749, the town had just a handful of structures. Today you can visit the log and stone building (Washington’s Office Museum) that Washington may have used as his headquarters while overseeing the building of forts during the French and Indian War. Next to the city’s visitor center (located near Shenandoah University south of downtown) are two historic buildings: a log cabin dating to 1780 and an early settler’s 1754 limestone house, now a museum.

Much history and many more beautiful old homes and buildings from all eras can be seen in Old Town Winchester; Touring the Shenandoah Valley Backroads provides a detailed walking tour. Winchester is also proud of its Civil War heritage—it’s said that the town changed hands more than 70 times during the war. Three major battles took place in and around the city.


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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