Winchester, Virginia — the Heart of Shenandoah Valley & the Civil War

July 12, 2026 paperbacklou Americas 0
Old Town Winchester, Virginia

A trip to Winchester, Virginia is recommended as a fulcrum for a trip exploring the entire Shenandoah Valley — one of the most beautiful areas of the United States — and location for many Civil War and some French-Indian War battles.

Winchester is a small city in the Northwestern part of Virginia. It is about 10 miles from West Virginia (which creates crazy weather reports, “rain coming East from West Virginia” etc). It is also 10 miles south of West Virginia — which juts over Virginia at its northwest corner.

Winchester is called the Heart of Shenandoah Valley, even though it is situated at the Northern most part of the Valley which extends 400 miles to the South.

Heart of the Civil War

Winchester exchanged hands between Union and Confederate forces 72 (seventy two) times during the Civil War — a record. That and more makes Winchester a kind of Heart of the Civil War. The hotels in downtown Winchester (now called Old Town) were turned into hospitals in the Civil War; the Courthouse was turned into a jail; General Stonewall Jackson and General Robert Sheridan had headquarters there — several blocks apart! See more below.

George Washington Got His Start Here

George Washington got his start in Winchester — first as a surveyor, then in 1754, when France refused to withdraw from the Ohio Valley, he led a surprise attack at Jumonville Glen that sparked the French and Indian War. From 1755 to 1758, Washington commanded Virginia forces from Winchester, overseeing the construction of Fort Loudoun (a remnant of which is still in Winchester) and other frontier forts.

Heart of the Shenandoah Valley

There are several places in Winchester that describe it as the Heart of the Shenandoah Valley. You wouldn’t think it was, since it is not in the middle of the Valley but rather at its most Northern point — it is more like the Brain of the Shenandoah Valley. But that’s what they call it. You’ll see this in signage at the George Washington Hotel in Winchester, for example — a grand old hotel that could claim to be the Heart of Winchester.

The Apple Capital

Winchester is also known as The Apple Capital — the area is known as one of the country’s richest Apple-growing areas, with Apple farms all around. There are numerous farmer’s markets and stores where you can buy fresh-picked apples of several varieties. Each year Winchester hosts an Apple Blossom Festival, that goes back over 100 years to 1922.

What to Do On a Trip to Winchester & Shenandoah Valley

A trip to Winchester means you are taking a trip to the Shenandoah Valley — so there are things to do in town, and things to do outside town:

1. Eat & Drink in Old Town Winchester

Old Town Winchester should be your first stop, or last stop — or ultimate stop. It is not only a lively town for live music, restaurants, and drinks — it is STEEPED in Civil War history.

The center of Old Town is Loudoun Street. It has several restaurants and bars with outside eating. On Thursday thru Saturday nights during the warm months from Spring to Fall there is live music on the street.

The video below was taken by me sitting on the steps of what used to be the Courthouse, which was turned into a jail in the Civil War — where many died. Dead bodies used to be piled on the top of the steps where I was sitting taking this video. Today the building is a Civil War Museum.

An old bank on Loudon Street has been turned into the Union Jack Pub — highly recommended.

Have a Drink & Listen to Music at the George Washington Hotel

Just off Loudon Street is the George Washington Hotel — who remember got his start in this town. The hotel has a beautiful lobby and active bar that typically has someone playing live music at the piano. I recommend spending some time here for some drinks and music — wonderful atmosphere.

The lobby features pictures of past events, including prior Apple Blossom parades — which Hollywood celebrities Grand Marshall each year — from Bing Crosby to Bob Hope to Captain Video to Adam West. They still do: Dean Cain was the Grand Marshall in 2022 for example. The parade is held the first week of May.

Graphic on the wall of the George Washington Hotel shows prior Grand Marshalls of the Apple Blossom Parade. Click to see full view.
Photo in lobby of George Washington Hotel of an Apple Blossom Parade from years ago in Winchester.

Watch the Railroad that Runs Through It

A railroad runs through the center of town. There is nothing like a warm summer night in Winchester with the sound of a freight train coming through — and then to see the freight train come through. Here is a video shot from the old Federal Courthouse on a late June evening — with the sound of the train in the background. The train comes through several times each night. PS: there were incredible cumulous clouds that evening.

It is a short freight line called the Winchester and Western Railroad (WW), which runs 53 miles of track in the Shenandoah Valley, running from Gore, Virginia — through Winchester — to Hagerstown, Maryland.

The train also has a New Jersey line. It carries sand from the Unimin sand quarry that it picks up at Gore, Virginia and distributes. It also carries grain, lumber, and fertilizers. It hooks up with CSX and Norfolk Southern main lines.

2. Examine Old Town Winchester for Civil War Experience

While you are in Old Town — look around — you are in the HEART of the Civil War. All of the buildings are of Civil War vintage.

Check Out the Old Hotel — Which Was a Hospital

The hotel and several homes in the old downtown of Winchester became hospitals during the Civil War, and housed hundreds — probably thousands — of both Confederate and Union troops during the war. In the video below, the building to the right (with the columns) is the old hotel which transformed into a hospital, and is now an eatery/bar.

Check Out the County Courthouse — Which Was a Horrific Jail

Prisoners were housed in and outside the County Courthouse, that still stands at the center of town, and is now a museum. Both sides used the Courthouse as a prison and a hospital — so sometimes there were Northern prisoners there and sometimes Confederate prisoners, as the town exchanged hands 72 times.

As a jail in the Civil War it was a gruesome place. The courtyard was enclosed by fences. As soldiers died from wounds or disease, they be piled up on the top of the steps at the front of the courthouse.

The courthouse features the Statue of the Confederate Soldier at its front.

Old Town Winchester Federal Courthouse, which was turned into a jail in Civil War, and is now a museum. The Statue of the Confederate Soldier is at its front.

You can click the picture below to get a full size view of it and zoom to the lower right to read the placard.

Old Town Winchester Courthouse turned into Jail in Civil War — and now a museum. Click to open full size version and read placard to right.

The placard reads:

During the Civil War, the Union and Confederate armies each used the Frederick County Courthouse as a hospital and a prison.

Cornelia McDonald, a local citizen, nursed the wounded here after the First Battle of Kernstown on March 23, 1862. She later wrote, “I went to the court house; the porch was strewed with dead men. Some had papers pinned to their coats telling who they were. All had the capes of their coats turned over to hide their still faces; but their poor hands, so pitiful they looked and so helpless… Soon men carried them away to make room for others who were dying inside.“

Sgt. Henry Peck was one of the 63 soldiers of the 118th Pennsylvania Infantry (the Corn Exchange Regiment) captured at the Battle of Shepherdstown (in present-day West Virginia) on September 20, 1862, and briefly imprisoned here. Peck later wrote, “In Winchester we were consigned to the court-house and the enclosure between it and the street. There were already in these precincts a crowd of some 300 rebels, strugglers, conscripts and the riff-raff a provost-guard can pick up — a miserable lot — who did not fraternize with our men, and were so filthy in clothing and in habits that our men remained of choice in the open yard without tents or blankets, even during nights of hoarfrost, to avoid contact with those in the court-house, which we were otherwise free to occupy.“

Visit the Civil War Museum in the County Courthouse

You can enter the courthouse itself for a small fee — it is now a Civil War Museum — and is highly recommended.

Visit General Stonewall Jackson’s Headquarters

Stonewall Jackson at one point had his headquarters in Winchester. His headquarters is now a museum; for $15 you can take a wonderful tour of the place. When I was there, the lady giving the tour showed us a couch that Stonewall Jackson had gifted to his sister for her wedding, which occurred during the war. Transporting a couch was a big thing to do in those days — on horse-and-buggy over many miles in the middle of war. The story goes that she rejected the gift because he was with the Confederates. So the couch was returned and remains in his headquarters in Winchester to this day.

General Stonewall Jackson’s Headquarters in Old Town Winchester, Virginia. Now a museum.

Check Out Sheridan’s Headquarters

General Sheridan had his headquarters about 8 blocks away from where Stonewall Jackson had his headquarters. The building that housed Sheridan’s headquarters is still there — but it is a clothing store now.

Sheridan’s Headquarters is now a clothing store — 135 North Braddock Street in Winchester, Virginia.

Check Out George Washington’s Fort Loudoun

Also in Old Town, Winchester are the remnants of George Washington’s Fort Loudoun — the fort is long gone — but the well that he dug at the fort is still there, in the backyard of an administration building that was built in 1830 (long after he passed in 1799).

Administration building on the remnants of Fort Loudoun. The fort  was erected by commander George Washington during the French-Indian Wars.

Colonel Byrd (Who Flew to South Pole) Was from Winchester

Colonel Richard Byrd — the Explorer who was first to reach the South Pole by plane (a Ford Tri-Motor Coach) — was from Winchester. There is a tribute to him in Old Town Winchester.

3. Visit Civil War Sites Outside of Town

Visit the Railroad Crossing at Piedmont Crossing

A 20 minute drive south from Winchester gets you to Delaplane and wine country — there are several wineries. But just as interesting is Piedmont Station, where for the first time, Confederate troops boarded trains to enter the war — to the fray at the first Battle of Bull Run in Manassas.

Visit Antietam Civil War Battlefield

A drive north from Winchester to Sharpsburg, Maryland gets you to Antietam National Battlefield — the bloodiest battle in the Civil War. You can spend several hours at Antietam. The town of Sharpsburg itself has some historical buildings.

Drive to Capon Bridge & Romney, West Virginia — View More Civil War & French-Indian War Places

A 30 minute drive west from Winchester gets you to Capon Bridge, West Virginia.

There you can view Edward’s Fort Stockade, used by George Washington’s troops in the French Indian Wars. It provided a safe haven a day’s March from headquarters in Winchester, VA. They’d cut slats in wood to shoot from behind.

Capon Bridge is an amazing little town, with a library, and an arts and music cafe.

A short drive past Capon Bridge gets you to some farms that have Black Angus cows. You are right by the Potomac River — inland long before it gets to Washington DC.

A 20 minute drive further west gets you to Romney, West Virginia. Along the way you’ll spot placards for other history Civil War and French-Indian War places.

4. Enjoy the Shenandoah River

And of course there is the amazing Shenandoah River, which cuts through the whole region, south to north.

Wade in the Shenandoah River Water

If you are in the area it is a must to wade in or at least touch the Shenandoah River. As John Denver sang, “Blue Ridge Mountains, Shenandoah River.”

There are spots to wade in the river if you drive south along Route 340N from Front Royal to Luray.

Go Rafting in the Shenandoah River

You can also rent a canoe or a raft and going rafting down the Shenandoah.

5. Eat in Harpers Ferry

Harper’s Ferry is a destination all to itself — and we write about it in another article.

If you are in Winchester, Harper’s Ferry is a quick 30-minute drive North. It features a quaint town on the junction of where the Potamac and Shenandoah Rivers meet. Lewis and Clark stockpiled goods here for their journeys west a million years ago, and Harper’s Ferry is most known for the John Brown rebellion at the start of the Civil War. There is a multi-building museum of the John Brown era, and there are some nice restaurants and ice cream places in town.

Visit/Camp in Harpers Ferry Civil War Battlefield Campground

Just above Harper’s Ferry is the Harper’s Ferry Civil War Battlefield Campground — a highly recommended place to chill out at — even if you are not camping there.

6. Take Skyline Drive

It is highly recommended that you take a few hours to drive on Skyline Drive — which takes you up onto the Blue Ridge Mountains for a drive north to south or vice versa. Its northern access point is just outside of Front Royal — 20 minutes south of Winchester. You can drive it for miles and miles — come off it — get back on it, etc. It is a toll road but well worth the money. Fantastic views.

7. Visit a Winery

There are some amazing wineries just east and south of Winchester. You can drive in, check out some wine, and buy a bottle or two. Highly recommended is Delaplane Cellars — in Delaplane, a 20-minute drive from Winchester down Route 50 to Route 17.

8. Visit Luray Caverns

Luray Caverns is an hour south of Winchester in the middle of the Shenandoah Valley. You can drive down to Front Royal, drive thru the Skyline Drive, then drive over to Luray where the caverns are.

The price per person at this writing is $35.

9. Visit the Winchester Airport

If you are in Winchester, don’t forget to spend some time at the local airport — the Winchester Airport — which has a fabulous lobby with model airplanes suspended from the ceiling.

And watch the planes take off and land.

Where to Stay

I stayed in Winchester 4 nights a week for 2 years while on the job. My favorite places to stay were:

  • The Travelodge in Winchester — family run. Good price. Clean. Wonderful people.
  • La Quinta Inn in Winchester — a little more expensive than The Travelodge, but more modern and fun.
  • George Washington Hotel in Winchester — more expensive than the other two, but a historic hotel with amazing lobby.

 

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