Winchester is an old Virginia city in the historic and scenic Shenandoah Valley, so it starts out interesting. But there are a bunch of specific things here in town worth checking out.

They include:

In the neighborhood of the Museum:

Winchester-Frederick County Visitors Center – Recently under new management, this does what these agencies do, and does it well. Don't expect to learn history here, but you're coming to the Museum anyway. But here's where you can learn about what's going on in Winchester. Of course, you can also check their website before you visit. 1400 S. Pleasant Valley Road, Winchester, VA 22601 (540) 542-1326

Shawnee Springs Preserve – probably the City of Winchester's oddest and least used park. I might do walking tours in this area. The park including visible signs of when the Springs were a key part of Winchester's water supply, and some signage showing this was part of a huge field hospital for the U.S. forces during the War of the Rebellion. It also has paths forged by homeless people and wanderers that go to adventures for those so inclined. Hollingsworth Drive, Winchester, VA 22601

The Patsy Cline House -- just a few blocks away at 608 South Kent Street. This loving reconstruction of the average working class family home where country music's tragic songstress grew up is worth a visit if you are Crazy or prone to Walkin' After Midnight. 540-662-5555

Shenarts/Shenandoah Arts Council, just a block south just of the Museum at 811 South Loudoun, is a community arts center that honors today's community treasures, from the graphic arts to theater to music to fun. Limited hours. (540) 667-5166

Downtown Walking Mall – Winchester's Community Focus

Nine blocks north of the Museum is Winchester's Downtown Walking Mall, which features stores, much good dining, and is close by the key local government agencies. Also nearby are most of Winchester's dominant churches, and the site of George Washington's Office at 32 W. Cork St, a small city-owned museum that covers Washington's time in Winchester as a youth and young man.

Right at the northern end of the mall is the Winchester Book Gallery, owned and run by a local family and a great source of local historical material as well as all kinds of reading. 185 N. Loudoun Street. 540.667.3444

The Mall also includes a made in Chicago generic statue of a Rebel soldier. Erected in 1915, it is one of the least historic and meaningful objects in Old Winchester.

Just west of the Mall is the former site of Robert Orrick's home. Orrick was born into slavery, and became an entrepreneur even before he became free. After Emancipation, he became quite wealthy, and endowed churches and a cemetery for the Black community. (This site is listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at

East of the mall it's only a couple of blocks to the Old Stone Church at 304 E. Piccadilly Street. Built in 1788 as a Presbyterian Church, it also served as the public school for Black children from 1878 to 1927. (This site is listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at

Local Revolutionary War hero Daniel Morgan is commemorated with a statue in front of the church.

Nearby, at 232 E. Fairfax Lane, is the Cartwright Funeral Home, established in the 1930s to serve Black residents, and still in business. (This site is listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at

To the east of the Old Stone Church are two historic cemeteries, whose separation reflects the ongoing impact of the War of the Rebellion.

Winchester National Cemetery began as a cemetery for U.S. soldiers killed in the Third Battle of Winchester, which began to the north of the city but ended in this area. It continues to be a resting place for members of the U.S. Armed Forces up into modern times. Its solemn rows of uniform markers are interrupted by large 19th century memorials to some of the units whose members are buried here. Its entrance is on National Avenue.

Mount Hebron Cemetery is much larger, and has its entrance on East Street. It is in a sense four cemeteries, with two very old sections from old church cemeteries. The main section is the cemetery for many of Winchester's most notable white families, and features a wide variety of older tombs and memorials. Finally, towards the east, is the Stonewall Cemetery, one of the first established for soldiers of the Rebellion. It is divided into sections of soldiers from different states, and includes several monuments that reflect the Lost Cause sentiments of Winchester's and the South's white elite. Finally, the large gatehouse and the cast iron fence around the cemetery were donated by Charles Rouss, a wealthy former solider of the Rebellion who also helped fund Winchester's City Hall and various Lost Cause projects.

Near the south end of Mount Hebron Cemetery, but facing Kent Street, is the undistinguished building of the Winchester Star. This is only a notable spot because the Star is still owned by the Byrd family, and still expresses the racist Lost Cause politics of Harry Flood Byrd Sr. to the extent that the 21st century will allow them. From the 1940s, when the Star moved to this location, until his retirement from politics in 1965, this was Harry Flood Byrd Sr.'s political home. Gee, I can't seem to link the website of this newspaper. But it's behind a paywall anyway.

Also in this area are two key Black History sites, neither one open to the public. The home at 119 East Lane was the home of Powell Gibson, an educator and community inspiration, from 1916 to 1959. The now vacant building at 224 Sharp Street was a beauty shop, a grocery store, and for many years a hotel for Black people. (Both sites are listed on the Virginia Foundation for Humanities African American Historical Sites Database, at


North Kent Street makes a transition to Winchester's Black community. In the 200 block of North Kent, you will sometimes find me at Chop Stick Cafe, an excellent and busy Thai restaurant, and sometimes at Just Us Barber Shop, a Black-owned shop with decades of history.

Farther north, you will find a historic building, not generally open to the public, that serves an African-American Elks Club. The stone building is one of Winchester's oldest, and has served many uses, including at one point a stable. 414 N. Kent St. (This site is listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at

At 440 N. Kent is Stephen's Restaurant and Jazz Cafe, a Black owned business. Call first to make such they are open. (540) 431-5384

Next door is the childhood home of John Kirby, who led a successful Manhattan jazz combo in the 30s and 40s. Like Patsy Cline, he achieved musical success by leaving town. He attended the school in the Old Stone Church. The home is not open to the public. (This site is listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at

At 598 N. Kent St. is the former Douglas School, which served as the elementary (only) school for Blacks from 1927 and from 1953 as a high school. It was a center of the Black community until the end of segregation, and its memory is still treasured at an annual reunion. The building, like the library and Handley High School, was built with funds from a wealthy Pennsylvanian with personal attachments to Winchester. However, it has not been maintained and treasured like those buildings. Just recently, the school system made a decision to use it for administration, which led to the ejection of community services to children located in the building. (This site is listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at

You will also find information here.)

Across the street is George's, at one time a major site for concerts and recreation for Winchester's segregated Black community, and still a place for down-home food and community gathering.

Just west of Kent St., but across the railroad tracks at 439 N. Cameron St., is the former site of Brown's Barber Shop, which was an important Black meeting place, where the Winchester NAACP and other Freedom Movement efforts were organized. One more block west is St. Paul African Methodist Episcopal Church, at 428 N. Loudoun St., founded in 1867. (These sites are listed, and more information is provided, on the Virginia Foundation for Humanities African American Historical Sites Database, at


The next four items are at the corners of Piccadilly and Braddock Sts., two blocks west of the Walking Mall, going clockwise from the northwest corner.

NW) Handley Regional Library -- a monumental building for a small city's library, worth just looking at inside and out. In the basement are the Stewart Bell Jr. Archives. While they are most often used by those nostalgic for the Slavery Rebellion and their white Valley ancestors, they provided a lot of the information we share in the Museum. 100 West Piccadilly St. (540) 662-9041

Go here for more about the library building.

NE) The Hideaway Cafe -- directly across Braddock Street is a woman-owned business that in its first year of operation has become a safe space for LGBTQ people, young students, activists and human beings in general. It's also comfortable and a source of good coffee, simple meals and snacks. 200 N. Braddock Street. 540-450-0799

SE) Tropical Island Coffee Cafe -- also at this corner, easy to find because of the sound of reggae and island music on the outside speakers, is this relaxed and authentic source of Jamaican staple foods and treats. Its owner Lloyd Washington is a mainstay of Winchester's community but true to his Jamaican roots. 39 W Piccadilly St Winchester, VA 22601 (540) 905-8022

SW) And finally, in the southwest corner, the Logan House, now a women's clothing shop, is the site from which for almost six months U.S. General Robert Milroy administered the City of Winchester-- perhaps the most dramatic moments of the Civil War for Winchester civilians.

A little farther west, at Amherst and Boscawen, there is a lot of history, but it's mostly not visible. The boyhood home of Virgina political boss (a major subject of the Museum) Harry Flood Byrd Sr. was at 326 Amherst St., but was demolished in 1969. A vacant drugstore now occupies the site. The only sign of its history is a marker that commemorates Harry's brother, Admiral Richard Byrd. There is no mention of Harry.

Just west at 514 Amherst is a private home whose stone gatepost bears the name “Selma.” The house was built in 1872, on the site of the demolished home of James Murray Mason, a fierce proponent of of the Southern elite who, as a US Senator, wrote the 1850 Fugitive Slave Act. Mason lived in Winchester for 40 years, and raised his family at the former Selma house.


Way off on the western edge of Winchester is The Museum of the Shenandoah Valley. This is a fairly large regional museum. It has exhibits about the Valley that seek to be culturally aware, and sometimes succeed. So they had an excellent and very powerful exhibit it of Black quilts, but also an exhibit of Hollywood costume design. 901 Amherst Street Winchester, VA, 22601. 888-556-5799

There are old tools, furniture, etc. that can move you, but of course most that survive belonged to the more wealthy.

Finally, of perhaps the greatest interest, the Museum of the Shenandoah Valley has in recent years faced the fact that the original house and grounds -- open during warmer months -- were transformed by its final owner, a Gay man, and his partner, during their years there to their tastes. The grounds include a Chinese themed section, lots of statuary, and elaborate gardens, and reflect what two Gay men could do with some money back at a time when Gay self-expression was often restrained and closeted.

Third Winchester Battlefield – While the Battle of Third Winchester was fought in September 1864 right through to downtown Winchester, the preserved battlefield is to the northeast of the city. It has two entrances. The one at 541 Redbud Lane is open all day. The other adjoins the parking lot of two Frederick County Schools, and parking is only available there during non-school hours. The actual sites of the battle, including the slope down to Redbud Run where U.S. forces led by future President Rutherford B. Hayes charged into the fire of Rebellion troops, are well marked. But the preserved Battlefield also serves local people as a great space to run, walk, birdwatch, and enjoy wooded areas.

Thrift stores – the area generally around the corner of Weems and Valley Avenue includes the Goodwill, Salvation Army, SPCA, and Blue Ridge Hospice thrift stores, as well as an upscale used book store, Blue Plate Books, and the idiosyncratic Valley Discount store. There are some good “junktique” places, including Present & Past's two locations north of downtown, and Blue Peacock Antiques, only a few blocks from the Museum and the source of some interesting artifacts in our collection.

Restaurants: Winchester does not have all of the cuisines available in places like Washington DC or Richmond. We do have respectable examples of Thai, Indian, Chinese and Vietnamese cooking, as some interesting variations of the Greek diner that was a staple here once and on upscale Italian, as well as various kinds of Mexican. There are several independent coffee shops as well as Starthings'. There does not seem to be one place that everybody would agree is “the” place for old-fashioned Winchester native food, but Apple Valley Cafe at 674 N. Loudoun St. would be a good candidate.


Not So Much

The Stonewall Jackson House This house, owned by the city, was occupied briefly by Thomas Jackson (thug name Stonewall). Jackson did not administer the City or spend much time interacting with its people; he was in the business of tearing around the countryside.

Now, however, this house that was little more than a nice motel to Jackson has become a shrine to him. The house is genuinely historical and well-preserved, and should be displayed for its meaning to Winchester. But instead it is tarted up as a Rebellion shrine, even to the point of a cannon in the front yard. I don't know much about military strategy, but I doubt that Jackson had a cannon in the front yard of the place where he and his wife slept in the middle of a Rebellion-occupied city. If it was free to visit the place, I would recommend the place as an excellent example of Fake History.

The old Frederick County Courthouse, located right behind the Mall's Rebel statue on the Walking Mall, is now billed as the Shenandoah Valley Civil War Museum. If you are fascinated with endless displays of Civil War weapons, uniforms, and ammunition, it's your kind of place. If you think of the Civil War more as an event that involved human beings, maybe not so much.

Jubal Early Avenue, which despite the name has zero historical meaning, being a road built and named in the 1990s. Early did lead the Rebellion forces at the Third Battle of Winchester, but he had much greater impact as a propagandist after the war. He made a good living as a spokesmodel for the corrupt Louisiana Lottery, while he re-invented Robert E. Lee as a God-like figure that never actually existed.

Anyway, most of the area south of that Avenue, especially on Pleasant Valley Avenue, consists of the same stores and fast food joints you have in your town. Don't bother to head South across Jubal Early Ave unless you are going on to Middletown or points south or need a bix box or fast food fix.

Considering coming to Winchester to see the Virginia Museum of Veiled History?

Not sure what else to do here in Winchester VA?