20 Things To Do In Winchester VA

Winchester is in northern Virginia in the Shenandoah Valley and a perfect southeastern U.S. small-town vacation destination offering a mix of new attractions and old historic sites. There are museums, vineyards, wetland preserves, parks and trails to discover. Even better, Winchester is just two hours from Washington DC so it’s a fantastic destination for a day trip or a long weekend.

Winchester, Virginia

20 Things To Do In Winchester

1- Visit The Museum of the Shenandoah Valley

The Museum of Shenandoah Valley is an impressive building from the outside and full of impressive treasures inside.

This museum houses more than 23,000 objects ranging from archival materials to decorative arts.

The Julian Wood Glass Jr. Collection, Gardens and Grounds, Glen Burnie Queer and the Wood-Glass Family Archive can all be viewed at the museum.

There are also a variety of temporary exhibits at the museum.

Past exhibits have focused on pop art, Latin America, origami, and a National Geographic photo collection.

The Museum of the Shenandoah Valley is at 901 Amherst St, Winchester, VA 22601.

2- Step Back In History At Abram’s Delight

Abram’s Delight is the oldest house in Winchester, built in 1754.

This house is quite juxtaposed to the modern city of Winchester but it allows visitors to imagine what life was like 250 years ago.

Abraham Hollingsworth arrived in the Valley in 1728 and he was looking for a place to build his family home.

He received a grant and first built the log cabin that you can see just west of the main property.

The house also served as the first Quaker meeting house.

As you look around the property you can see an array of period art and antiques.

The house is open between April and October from 10 am to 4 pm Monday to Saturday and from 12 pm to 4 pm on Sunday.

Abram’s Delight is at 1340 S Pleasant Valley Rd, Winchester, VA 22601.

3- See George Washington’s Office Museum

The George Washington’s Office Museum is another wonderful Winchester attraction where you can learn more about both local and American history.

When you arrive at the museum you will see a little log building.

This building was used by George Washington as a military office between September 1755 and December 1756 during the construction of Fort Loudoun.

Washington was responsible for overseeing the construction of the fort as well as planning.

He even brought his own blacksmith from Mount Vernon.

George Washington’s Office Museum is at 32 W Cork St, Winchester, VA 22601.

4- Admire The Architecture At Hadley Regional Library

The Hadley Regional Library is a fine example of Beaux-Arts architecture.

The impressive arches to the entrance of the library coupled with the teal-colored domed roof make this one of the most beautiful buildings in Winchester.

The library was funded by a $250,000 will donation from Judge John Handley of Scranton Pennsylvania.

The Hadley Library opened in 1913.

Wander around the impressive library then take some quiet time to explore inside.

If you are staying in Winchester for a few days then pick up a book for your vacation.

Hadley Regional Library is at 100 W Piccadilly St, Winchester, VA 22601.

5- Discover Old Town Winchester

Heading to Winchester’s Old Town has to be high on your list of things to do in the city.

This downtown area is full of charming, plenty of restaurants, cute shops, historical landmarks, museums and centuries old architecture.

There’s always something going on in the Old Town.

From concerts and markets to movies and beer festivals there’s always a hive of activity.

There’s even a splash pad in summer for kids.

6- Discover History At Third Winchester Battlefield Park

The Third Winchester Battlefield Park includes more than 600 acres of preserved land.

This historic area commemorates the Third Battle of Winchester which was fought on September 19, 1864 during the American Civil War.

This was the largest battle fought in the Shenandoah Valley and one with the most casualties.

Over 54,000 troops fought and there were 8,600 casualties.

While at the park you can explore the six miles (9.6 km) of walking trails and read the 30 interpretive markers and monuments that tell the story of the Third Battle of Winchester.

Third Winchester Battlefield Park is at 541 Redbud Rd, Winchester, VA 22603.

7- Visit Shenandoah Valley Civil War Museum

Right in the heart of downtown Winchester you will find the Shenandoah Valley Civil War Museum which is within the Frederick County Courthouse.

This impressive courthouse was built in 1840 and has been used as a hospital, a prison and barracks during the Civil War.

The museum’s exhibits tell the story of the Civil War in the Shenandoah Valley.

You can read the words of people who lived through it while discovering artifacts from the time.

You will be able to learn about battles and the everyday lives of soldiers and civilians.

Shenandoah Valley Civil War Museum is at 20 N Loudoun St, Winchester, VA 22601.

8- See Patsy Cline Historic House

Patsy Cline was one of the most influential American singers during the 20th century and she was born in Winchester, Virginia.

The Patsy Cline Historic House was Patsy’s home between the ages of 16 and 21 from 1932 and 1963.

While visiting the house you can see photographs and furniture that would have been there during the era she lived in the house.

The Patsy Cline Historic House is on the National Register of Historic Places and is at Cline Historic House is at 608 S Kent St, Winchester, VA 22601.

9- Step Back Into The Past At Mount Hebron Cemetery

A cemetery doesn’t sound like the most joyful of places to spend a vacation but Mount Hebron Cemetery makes for a really interesting visit.

Many of the graves date back to 1760.

In one part of the cemetery there is the Lutheran Church which is surrounded by graves.

You can also visit the Stonewell Confederate Cemetery which is the final resting place of more than 2500 Confederate soldiers.

Mount Hebron Cemetery is at 305 E Boscawen St, Winchester, VA 22601.

10- Have Fun At The Shenandoah Apple Blossom Festival

This festival is super fun and one that attracts more than 250,000 people over the course of the 10 days.

The event is usually held at the end of April and the start of May each year but it’s best to check in advance to see the specific dates.

This fun spring celebration includes the Old Town Wine & Fine Arts Festival, the Apple Bloom Carnival, parades, sports events, parties, luncheons and dances.

There’s literally something for all ages and interests.

The Shenandoah Apple Blossom Festival is at 135 N Cameron St, Winchester, VA 22601.

11- See The Collection At Stonewall Jackson’s Headquarters Museum

This historic house was built in 1854 by William McP. Fuller was used by General “Stonewall” Thomas Jackson during the winter of 1861-1862.

Inside the house/museum there is the largest collection of Jackson memorabilia.

The museum also contains personal effects from some of Jackson’s personal staff.

You can see Jackson’s prayer table and prayer book.

If you are interested in the Confederates and the American Civil War this museum is well worth checking out when you visit Winchester.

Stonewall Jackson’s Headquarters is at 415 N Braddock St, Winchester, VA 22601.

12- Learn Something New At Shenandoah Valley Discovery Museum

There’s no doubt about it, Winchester has its fair share of museums.

The Shenandoah Valley Discovery Museum has four floors for you to discover.

There are maths and science displays, hands-on activities for the kids and humanities and art exhibits.

You can learn more about Native American culture, learn about palaeontology and see what it’s like to be a doctor in the emergency room.

There are also a ton of activities for the little ones including sensory play!

Shenandoah Valley Discovery Museum is at 19 W Cork St, Winchester, VA 22601.

13- Admire Rare Plants at Abrams Creek Wetlands Preserve

The beautiful Abrams Creek Wetlands Preserve is a wonderful place to escape the city to relax among 300 plant species and 180 different kinds of birds.

20 of the plant species in the preserve are included on Virginia’s Rare Plants List.

There are many trails around the preserve which wind in and around the marches, swamps and trees.

The Abrams Creek Wetlands Preserve is at W Jubal Early Dr, Winchester, VA 22601.

14- Wander Around Fort Loudoun Historic Site

Fort Loudoun Historic Site showcases the remains of a 19th century British fort.

As you will learn at George Washington’s Office Museum, Washington himself oversaw the construction of Fort Loudoun.

Fort Loudoun was built between 1756 and 1758.

It was named after John Campbell the 4th Earl of Loudoun who commanded the British forces in America during the war.

Check out the visitor center for more information on the fort.

There are also re-enactment days which are a whole lot of fun to watch.

Fort Loudoun Historic Site is at 419 N Loudoun St, Winchester, VA 22601.

15- Pick Fruit At Marker-Miller Orchards

There’s so much to see and do at the Marker-Miller Orchards.

The orchard consists of 325 acres of apples as well as a whopping 15 acres of peaches, and plums and pears as well.

Their Farm Market Bakery serves some incredibly delicious baked goods including the famous apple cider donuts.

Throughout the year there are many fruits and vegetables that you can pick for yourself.

In July expect peaches, raspberries, blackberries and tomatoes.

In August ginger gold apples and gala apples.

When the spooky season approaches its time to pick 12 varieties of apples, pumpkins and winter squash.

This is a great place to go for an outdoorsy date or with the family.

Marker-Miller Orchards is at 3035 Cedar Creek Grade, Winchester, VA 22602.

16- Sip Wine At James Charles Winery & Vineyard

From orchards to vineyards the James Charles Winery & Vineyard is the Shenandoah Valley’s premier winery.

This winery is just outside of Winchester.

Some of their award-winning white wines include the Cuvée de la Reine and the 2021 JC SS Chardonnay.

Their reds include Cabernet Sauvignon and the 1913 Ameritage.

The winery offers several wine tasting options.

From their classic tasting to the seated Vintner’s tasting where you will be treated to wines and a wonderful Charcuterie board.

As autumn arrives you can even head to the winery fire pit for some warmth and a relaxing wine tasting. 

James Charles Winery & Vineyard is at 4063 Middle Rd, Winchester, VA 22602.

17- Relax In Jim Barnett Park

Jim Barnett Park is an excellent space if you want to feel the fresh air and get active without leaving the city.

Jim Barnett Park is more than 170 acres and there are plenty of amenities to enjoy.

There’s a playground, an indoor and outdoor pool, basketball and tennis courts, a rec center, gymnasium and a disc golf course.

You can also exercise on their fitness trails, the BMX track and try your luck at catching fish on the lake.

Jim Barnett Park is at 1001 E Cork St, Winchester, VA 22601. 

18- See A Performance At Bright Box Theater

Winchester’s Bright Box Theater is an award-winning venue that hosts live music and comedy nights.

Bright Box Theater hosts some of the best evening events in the Shenandoah Valley.

Some of their most popular events have included drag performances and murder mystery dinners.

Famous artists to play at the Bright Box include The Nighthawks, Dom Flemons and Tim Reynolds.

Bright Box Theater is at 15 N Loudoun St, Winchester, VA 22601.

19- Walk The Apparition Trail

The Apparition Trail is a fun 90-minute walking tour.

This tour will lead you around Old Town Mall and towards the Mount Hebron Cemetery for a spookier feel.

Whileon this tour you will hear the frightening tales of ghosts and the spirit of soldiers who fought and died in Winchester.

Your guide is enthusiastic and energetic and it does feel more like an outdoor Halloween-inspired performance.

Children under the age of 12 are allowed on the tour free of charge.

Tours start at 8pm from the front steps of the John Handley Regional Library.

20- Check Out Rouss Fire Hall

The three and a half story rounded tower with its conical roof is quite a striking building and its home to the Rouss Fire Hall.

On top of the tower roof, you will see a weathervane depicting a fireman, known locally as Old Uncle Jake (pointing out a fire in the distance).

Rouss Fire Hall is at 3 S Braddock St, Winchester, VA 22601.