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For three years, Union and Confederate soldiers pounded through the heart of Winchester, Va., shouting, shooting, and dragging wounded comrades into hotels, houses, and stables. The lower Valley gateway town had been a crossroads hub even before George Washington helped to build Fort Loudoun there in the 1750s, but the Civil War’s traffic was destructive. Winchester was a “race-course—one day in the possession of friends, and the next of enemies,” recalled Maj. Gen. Philip Sheridan, appointed in 1864 to head the Army of the Shenandoah. A town of some 4,400 in 1860, Winchester experienced the fury of three major battles, and four other fights occurred nearby. Roughly 200 homes were destroyed, and the town famously changed hands about 70 times. In the 1970s, the city’s government closed off several blocks of Loudoun Street and turned it into a walking mall, allowing visitors to ramble Old Town in the footsteps of Washington and Civil War soldiers while soaking up the charm of magnificent brick and stone buildings. Numerous restaurants and brewpubs also offer places to relax and discuss Winchester’s many layers of history. Every site listed here is within walking distance of each other, but you might want to drive to the cemeteries and Stonewall Jackson’s headquarters. –Sarah Richardson


Bell House

The Bells, a prominent Winchester family, survived Third Battle of Winchester shellfire in this home. Bell descendants moved out only in 2016, when the Shenandoah Valley Battlefields Foundation purchased the home. The home at 106-110 Cameron St. is being renovated and is occasionally open for tours.



This Confederate 12-pounder cannon shot was excavated near the Cedar Creek battlefield. Had it detonated, the iron balls and fragments would have caused havoc.


What War Left Behind

The 1840 courthouse is enjoying a second life as the Shenandoah Valley Civil War Museum. The first floor recreates the courthouse; the upper story contains displays of fascinating relics excavated nearby, weapons, and artifacts of soldier daily life—about 3,000 items in all. Check out graffiti by Union POWs and a display describing the intensity of women’s Civil War involvement in Winchester.


Hotel Reborn

The three-story Taylor Hotel at 119 N. Loudoun St., constructed in 1848 with impressive pillars and porches, stands right on the walking mall. Confederate General Stonewall Jackson used it as his temporary headquarters in 1861 and for subsequent battles, and the building was also used as a hospital. Neglect led to a partial roof collapse in 2007, but a major renovation in 2012 rescued the structure, which now houses a bar/casual restaurant, Macado’s (, on the first floor and apartments above.


Jackson’s Headquarters

The famous Stonewall used this six-room Gothic Revival cottage, a short walk from the old section of town, as his headquarters in the winter of 1861-62—joined for a while by his second wife, Mary Anna. Period items and Jackson memorabilia are on display in the house’s interior.


Research Mecca

Judge John Handley, a coal baron from Scranton, Pa., moved to the Winchester area in the 1870s, and in his 1895 will funded this magnificent Beaux Arts library, completed in 1913. The copper dome represents the spine of a book, and the wings stand for pages. The lavish interior will inspire your desire to read and learn, with its rotunda featuring stained glass and spiral staircases.


Smoke House

Wealthy tobacco trader Lloyd Logan built the imposing home at 135 N. Braddock St. in 1848. General Philip Sheridan used it as his headquarters, and began his immortal ride to the October 1864 Battle of Cedar Creek here. The full porch was added in the early 20th century. It now houses the boutique Kimberly’s, open daily. Confederate Peace Drive through the stone entrance of Mt. Hebron Cemetery to reach Stonewall Confederate Cemetery and a towering monument of a soldier, above, honoring the unknown dead of the Confederacy. More than 2,500 Confederates, many unknown, but including Brig. Gen. Turner Ashby and Confederate spy Mary Greenhow, are buried here. Dedicated in 1866, it was the first officially recognized Confederate cemetery.


Winchester National Cemetery

[quote style=”boxed” float=”right”]“The general plan…of the grounds…is much more artistic and pleasing to the eye than the stiff formality observable in the National Cemeteries of the United States.”

New York Times Reporter at the cemetery dedication, October 25, 1866[/quote]

Just east of the Old Stone Church and directly north of the Stonewall Cemetery lie nearly 4,500 Union soldiers, known and unknown, disinterred from various nearby battlefields and reburied here in 1866. Fifteen monuments honor Union regiments, corps, and states that had burials of soldiers here or participants in the Third Battle of Winchester.


Old Stone Church

This austere structure, erected in 1788, was built to be a Presbyterian Church. In 1858, it was leased to the Old School Congregation Baptist Church of Color for $500, and during the war Federal troops used it as a stable. After the war, it functioned as a school for black children. Easy to miss and now privately owned, it is just east of the roundabout on Route 7 entering town.


Three Strikes

The Valley town lent its name to three major battles.

First Battle
of Winchester,

May 25, 1862
Second Battle
of Winchester

June 12-15, 1863
Third Battle
of Winchester,

September 19, 1864



Presidential Experience

Colonel George Washington used this building as an office while Fort Loudoun was being constructed in the mid-1750s. A scale model of colonial Winchester shows the site of the fort. It is no longer extant, but its former location is marked by a plaque in front of a private residence at 419 N. Loudoun, a short walk north of the Old Town Mall.