The old Winchester courthouse is an iconic landmark that is now a Civil War Museum and is a must on anyone's list of things to do in Winchester Va.

The 5 best Things To Do In Winchester VA For History Buffs

Looking for things to do in Winchester VA that will satisfy the history buff in your family?

Well, you’ve come to the right place.

Winchester, Virginia has always been one of my favorite places to visit for both its stunning beauty and its rich heritage. Nestled in the Shenandoah Valley, this charming town has a long history that dates back to before the colonial era.

Read on to find out about some of the most popular things to do in Winchester, as well as hidden gems that will make you understand why Winchester is a must-see for history buffs.

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Planning to spend a night in Winchester VA? I highly recommend The George Washington Hotel (Wyndham). Elegant and convenient. Close to everything.

Background On Winchester VA

Lots of people know Winchester VA as the “Apple Capital” for its large apple industry and its annual Shenandoah Apple Blossom Festival. This popular event has grown from a one-day affair in May to a 10-day extravaganza that celebrates the agricultural industry, and draws crowds of more than 250,000 each year.

Winchester also has a vibrant downtown with lots of wonderful restaurants and shopping. And it doesn’t end there. Just beyond the city’s boundaries lie jaw-dropping views of the majestic Blue Ridge Mountains.

But the best things to do in Winchester for me relate to its history, and, as the oldest settlement in Virginia west of the Blue Ridge Mountains, Winchester has lots to offer.

So check out my list of things to do in Winchester VA that will enthrall lovers of history of all eras.

A bronze statue of General Daniel Morgan holding a rifle in front a stone church.
Frontiersman and Revolutionary War hero Daniel Morgan lived in Winchester.

Best Things To Do In Winchester For History Lovers

Winchester’s history is far reaching, starting with its use by the Shawnee Indian tribe as a camping ground. It’s not hard to imagine why the Native Americans would choose this area that is abundant with wildlife and natural beauty.

Winchester is also a touchstone in American history as a place where George Washington spent some of his teen years working as a surveyor’s assistant. He would return later to lead the way in building a fort to protect the frontier from the French and their Indian allies.

As you can see, we’re not even to the Civil War yet, and already so much history!

Truly, I had a very hard time narrowing down this list to only five things to do in Winchester, but here they are.

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1. Mount Hebron Cemetery, Winchester VA

The entranceway to Mount Hebron Cemetery in Winchester VA showing the sign and a stone castle-like structure.
The beautiful entrance to the historic Mount Hebron Cemetery in Winchester.

My first stop was the Mount Hebron Cemetery, and I ended up spending two hours in this serene resting place.

Of the more than 30,000 graves, some date back to the 1760s, which is interesting in itself.

But that’s not all. The cemetery also has a number of important historical figures laid to rest there, including General Daniel Morgan, who is credited with winning the Battle of Cowpens during the Revolutionary War among other notable accomplishments.

The Ashby Brothers, (Turner and Richard) are also interred there, both of whom were notable Civil War officers.

A tall monument stands among the gravestones at the Mount Hebron cemetery in Winchester. The sun is shining in a hazy sky.
The Mount Hebron Cemetery is a historic treasure that is a delight to explore.

The Stonewall Confederate Cemetery, which is a subsection of Mount Hebron, contains the graves of more than 2,500 Confederate soldiers who died as a result of the numerous battles and skirmishes that were found in the Winchester area.

The cemetery is laid out beautifully by state, and is truly something to see.

Related Post: Read about the death of Stonewall Jackson and visit the site where he passed away.

The ruins of the Lutheran Church at Mount Hebron Cemetery is one of the things to do in Winchester Va. A tree limb hangs in front of the stone ruins.
The stone ruins of the first Lutheran Church stand in the Mount Hebron Cemetery.

And last but not least, this historic cemetery in Winchester is the site of the ruins of the first stone Lutheran Church, whose cornerstone was laid in 1764.

Built by Winchester’s German population, it burned in 1854 but the surrounding cemetery continued to expand. The ruins have been beautifully restored and fit right into the scenic background of the cemetery.

Location: 305 E Boscawen St, Winchester VA

Note: Just across the road is the Winchester National Cemetery, where 13,000 Union soldiers from the Civil War are buried. There are 15 monuments in the cemetery, including a monument dedicated to the 54th Massachusetts Infantry Regiment, which was the first African American regiment to be raised in the North during the Civil War.

2. Stonewall Jackson’s Headquarters Museum

The side of the house that was used as Stonewall Jackson's headquarters is one of the things to do in Winchester. It is a yellow house with shutters and 2 flags are set at half-mast in the yard.
This house was used by Stonewall Jackson as his headquarters and is now a museum.

Another one of the most recommended things to do in Winchester is to visit Stonewall Jackson’s Headquarter’s Museum.

I have been in many historic houses, but this one truly stands apart because of the variety of original historical items that are preserved there. (Very different from Lee’s headquarters in Gettysburg).

For instance, the dining room table is the exact table used during General Jackson’s stay. His field desk is also there, and so is the small Bible that he carried (a gift from his sister) and a prayer table!

Visitors to the Stonewall Jackson’s Headquarters Museum can take a guided tour of the house and learn about Jackson’s time in Winchester and the history of the house.

The museum also offers a variety of educational programs and events throughout the year, including lectures and living history demonstrations.

Location: 415 North Braddock Street, Winchester, VA
Open April 1 through October 31.
Admission: $5; 4.50 for seniors, $2.50 for students K-12, and $12 for a family.

3. Old Town Winchester Pedestrian Mall

The brick-paved street of Old Town in Winchester with trees lining the street.
The street is empty in the early morning, but this is a vibrant area from late morning through the late evening hours.

Another one of my favorite things to do in Winchester is to take a leisurely walk through the Old Town Winchester Pedestrian Mall.

At about 250 years old, Winchester is one of the most charming Old Towns all over Virginia.

Quaint shops, cafes and restaurants dot the brick-lined street, so it’s a great place to grab a bite to eat or shop for gifts, books or clothing.

The Old Town of Winchester boasts over 30 restaurants, 60 shops, and several museums and historical sights.

If you’re in the mood for more history you can visit the Shenandoah Valley Civil War Museum or just looked at the architecture of the old buildings and soak up the history.

There are a number of historical buildings that are quite notable, including the Taylor Hotel, where Stonewall Jackson stayed briefly during the Civil War before moving his headquarters to a private home, and the First Presbyterian Church.

Plan to spend a few hours here. Like downtown Gettysburg, there is a lot to see and a lot to do.

4. George Washington’s Office Museum

Another of the popular things to do in Winchester visit George Washington's Office Museum. The plain brown building is pictured with a sign. The grass is green in the foreground.
George Washington’s Office Museum is a must-see in Winchester.

I have to admit that I found George Washington’s Office Museum to be one of the most unique and interesting things to do in Winchester during my visit.

George Washington used a little log building, now the middle room of George Washington’s Office Museum, as a military office from September 1755 to December of 1756 while he worked on building Fort Loudoun.

Located on the grounds of the museum is a cannon that was left by General Edward Braddock in Alexandria, which is an amazing artifact from that time period.

The displays in the museum include some of Washington’s personal effects, surveying equipment and a scale model of the town of Winchester circa 1755 which shows the fort he built prominently located at the north end of the town.

It’s a great place to learn about the early history of Winchester.

Interestingly, one of the “newer” additions to the original structure was used as a hospital during the Civil War and the blood stains are still visible.

I recently visited Mount Vernon, so it was interesting to visit Winchester where George Washington spent his early years.

If you’re interested in learning more about Washington, I recommend the Museum of the American Revolution in Philadelphia where you can see his actual war tent. From Philadelphia, it is a short drive to Valley Forge, where he camped during the winter of 1777.

George Washington’s Office Museum
Location: 32 West Cork Street, Winchester VA
Open daily April 1 through October 31
Monday through Saturday: 10 a.m. to 4 p.m. Sunday: Noon to 4 p.m.
Cost: Adults $6.00; Seniors $5.00; Students $3.00

5. Abram’s Delight

Abrams Delight, a white stone house with a small front porch is one of the oldest houses in Winchester.
Abrams Delight in Winchester Va.

Another one of the things to do in Winchester that caught my attention is getting to visit the oldest house in Winchester.

The original log house on the property of Abrams Delight was built by Abraham Hollingsworth in 1728, just west of the current stone house.

The beautiful stone house pictured above was built a little later by Abraham’s son, Isaac in 1754. Not long after its completion, Isaac and his family fled to Waterford in Loudoun County due to the threat of Indian attacks.

The house has been preserved and turned into a museum with exhibits that showcase the life and times of the early settlers of Winchester.

This is an interesting tour for the whole family and the Visitors Center is located right next door. Stop by and discover lots of other things to do in Winchester.

Location: 1340 S. Pleasant Valley Road
Season: April 1 – October 31
Hours: Monday through Saturday 10 a.m. to 4 p.m.; Sunday Noon to 4 p.m.
Admission: Adults $6; Seniors $5; Students K-12 $3

A picture of the main house at Belle Grove, a white limestone house against a blue sky.
Beautiful Belle Grove Plantation is located just outside of Winchester.

My list certainly doesn’t cover all of the things to do in Winchester because there are so many!

Here are a few other notable things to do in Winchester that have historic value and would be enjoyed by history buffs.

Site of Fort Loudoun: George Washington planned Fort Loudoun, supervised the work and brought his own blacksmiths from Mount Vernon to do the ironwork.

The fort was a redoubt with four bastions and had 14 mounted cannon. A well was sunk 103 feet through solid limestone rock to supply the fort with water and that well is all that remains of the fort today.

Patsy Cline Historic House: A must for music fans, this house showcases the life and legacy of the legendary country music singer who was born and raised in Winchester.

Shenandoah Valley Civil War Museum: This museum is located in the old courthouse building in Old Town and contains exhibits that showcase the history of the Civil War in Winchester. It’s a great place to learn about the battles that were fought in the area and the impact they had on the community.

Belle Grove Plantation: This historic plantation is right down the road from Winchester, as is the Cedar Creek Battlefield. Built in the 1790s, it deserves a post all to itself. (Soon!) You can tour the house or just walk the beautiful grounds.

Related Post: Historic Long Branch also offers beautiful grounds and a house tour.

Museum of the Shenandoah Valley: This museum is a feast for the eyes from its six acres of gardens to its 50,000-square-foot museum where you can explore the history and decorative arts of the Shenandoah Valley. An added bonus are the walking trails!

Handley Regional Library: The architecture alone of this historic library makes it worth a visit.

This statue of a 16-year-old George Washington stands in front of the George Washington office Museum in Winchester. Washington is depicted at 16 years old in bronze.
This statue of a young George Washington stands outside George Washington’s Office Museum in Winchester.

Plan Your Visit To Winchester VA

Winchester VA makes a great day trip from major cities, but one day is not going to be enough, no matter what your interests.

I recommend extending your visit into the Shenandoah Valley, where you’ll find plenty of things to do with kids.

If you’re planning to spend a night, there are plenty of accommodations to choose from in and surrounding Winchester.

My recommendation is The George Washington Hotel, located in the heart of downtown Winchester. This hotel features elegant rooms and suites, as well as a variety of amenities, including a fitness center and a restaurant.

The La Quinta is one of the many moderately priced hotel less than 2 miles from downtown.

If you want to splurge, try the Hillbrook Inn and Spa in Charles Town, WV., only 13 miles away. It has a restaurant and pub and serves a full English/Irish breakfast. It also puts you close to Harpers Ferry, another history-filled destination.

Hungry? I recommend Bonnie Blue for a great homecooked meal. I ate breakfast there, but they serve everything from Southern sides of collard greens to barbeque, catfish and crabcakes for main entrees.

A restaurant that is highly rated and located in Old Town Winchester is The Union Jack Pub and Restaurant featuring American, British and vegetarian dishes.

Wrap-Up Of Things To Do In Winchester VA

As you can see, this charming city has a rich history that is worth exploring.

Winchester also features abundant natural beauty and rich agricultural ties that provide a nice of mix of activities for the whole family.

I’m glad Winchester is only about 1.5 hours away from me in Gettysburg so I can do some more exploring in the future. (It’s also only 1.5 hours from Washington, DC and two hours from Richmond, VA).

I think you’ll discover that there are so many things to do in Winchester for history buffs, you will want to return again and again.

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