Lots of things to do in Winchester Virginia (for adults and families!)

This post may contain affiliate links. Click here to see what that means.

Winchester, Virginia, in the Shenandoah Valley alongside I-81, is a modern town with a rich history. There are so many things to do in Winchester, VA, it’s worth getting off the interstate to check it out.

If you’re taking a family road trip along I-81, add a day here to break up the trip! And if you live in Pittsburgh, Philadelphia, Baltimore, Washington or Richmond, there are so many things to do in Winchester, Virginia it makes a great weekend getaway destination.

If you only have a day, spend it on the Winchester Walking Mall in Old Town Winchester.

The Winchester Walking Mall

The Winchester Walking Mall, officially the “Loudoun Street Pedestrian Mall,” in Old Town Winchester is a two block stretch of shops, restaurants and attractions closed to street traffic. Each end of the Winchester Walking Mall has a clearly marked entryway.

Family waiting to cross Piccadilly Street and the north entrance to Old Town Winchester at Piccadillly and Loudon.

The Winchester Walking Mall is a popular spot for friends to enjoy dinner at a restaurant, most of which offer both indoor and outdoor dining. It’s also popular with families because it’s wide, tree shaded walkway is family friendly and inviting.

When looking for things to do in Winchester, Virginia, spending a day shopping, eating and exploring on the Winchester Walking Mall is a great choice. Here are just a few things you’ll find on the Loudoun Street Pedestrian Mall.

Winchester Walking Mall Splash Pad

In summertime, families enjoy the Winchester Splash Pad located near the southern end of the Loudoun Street Pedestrian Mall. Open seasonally from 10:30 a.m. to 7:00 p.m., the spray heads “dance” to the delight of young children. After dark, the splash pad becomes an art installation, illuminated in bright colors to entertain evening Winchester Walking Mall visitors.

Public restrooms next to the Winchester Splash Pad are open 8:00 a.m. to 7:00 p.m. daily.

Pets are not permitted in the splash pad.

Winchester Walking Mall children's Splash Pad with gray restroom building behind and benches/landscaping around the perimeter.

Shenandoah Valley Civil War Museum

Located at 20 North Loudoun Street near the center of the Winchester Walking Mall, the Shenandoah Valley Civil War Museum has preserved graffiti from both Northern and Southern soldiers who were imprisoned here during the Civil War. It also houses more than 3,000 Civil War artifacts, many gathered locally since Winchester was a key battle ground throughout the war.

Admission is $5 for adults, $3 for children with discounts for seniors, military, students and AAA members with valid ID. It is closed on Thanksgiving Day, Christmas Day and Easter Sunday.

Taylor Pavilion

Located behind the historic Taylor Hotel building, now a restaurant and condos, Taylor Pavilion is an open air venue just off of Loudoun Street with a wood frame covered pavilion. When not being used for private events, it’s a great spot to meet up with friends to chat or to enjoy a picnic lunch or a snack with the kids.

Taylor Pavilion behind Taylor Hotel on the Old Town Winchester Walking Mall. Purple patio umbrellas at iron tables in the foreground.

Dining and Shopping in Old Town Winchester

With beautiful weather much of the year, dining and shopping on the Winchester Walking Mall is truly enjoyable. Many local shops have been there many years, popular with locals and travelers alike.

People sitting at outdoor tables under blue umbrellas at a restaurant in Old Town Winchester, Virginia
People dining in Winchester, VA on a Thursday evening

I’ve eaten at several different places in Old Town Winchester, some on the Winchester Walking Mall and others nearby. It’s hard to keep up with all the changes as new restaurants come in, so check this guide to current restaurants in Old Town Winchester.

Many shops on the Winchester Walking Mall have been there for decades, like Florsheim’s Shoes and Thinker Toys. Others are newer. Local shops include just about everything like book shops, toy stores, shoe and apparel shops, and specialty shops. Check the current directory of shops in Old Town Winchester to see them all.

Beyond the walking mall in Old Town Winchester

The Winchester Walking Mall is the heart of Old Town Winchester. Just beyond these two blocks on Loudoun Street, you’ll find there’s much more to see in Old Town Winchester.

Fort Loudoun Historic Site

Located at 419 N. Loudoun Street, Fort Loudoun was a wooden fort built to supply the troops during the French and Indian War in the 1750s. George Washington designed the fort and supervised its construction. He also used it for his regimental headquarters during that colonial era war.

While the wooden fort is long gone, the home that now sits at the site serves as an interpretive center.

Patsy Cline House

There are more things to do in Winchester, Virginia than war history! Like the Patsy Cline House.

Located at 608 South Kent Street in Old Town Winchester, the Patsy Cline House is listed on the National Register of Historic Places. Singer Patsy Cline lived here for nine years, from 1948-1957, until her singing career took off.

The house is preserved as it would have been when she lived here, as well as photos of her performing through the years.

Hours vary, so check their Facebook page for current information.

Stonewall Jackson Headquarters Museum

During the Civil War, Winchester, Virginia changed hands approximately 72 times, more than any other place in the country. So, it should come as no surprise that Stonewall Jackson had headquarters here.

The house, located at 415 North Braddock Street, is another National Historic Landmark in Old Town Winchester, Virginia.

General “Stonewall” Jackson used it as his headquarters during part of the Civil War. The museum contains the largest collection of Jackson memorabilia, including his prayer table, prayer book and other family artifacts. It looks much the same as it did when he used it.

The museum is open April through October. Current admission prices are $10 for adults, $8 for seniors, and $4 for students K-12.

Great food in Old Town Winchester

When it comes to things to do in Winchester, Virginia, food is high on the list.

Sandwich: Baguette, tomato, lettuce, egg, bacon in a red plastic basket lined with paper
Breakfast Sandwich at Knead Bread Winchester, VA

Some of my favorite places around Old Town Winchester are:

  • Knead Bread at 28 E. Piccadilly Street, just half a block from the Winchester Walking Mall. Besides its punny name, Knead Bread serves an amazing breakfast sandwich, pastries and locally roasted Black Dog Coffee. This family owned company bakes each loaf and pastry fresh every morning. Each egg sandwich is made to order. And, the service is spectacular! Start your day here with a satisfying breakfast sandwich and cup of coffee.
  • The Tea Cart at 217 West Boscawen St. Winchester, serves a traditional British tea in a warm, inviting house just two blocks from the Loudoun Street Pedestrian Mall. If you have time for a full meal, I highly recommend the “Royal Ascot,” which includes a set menu of soup, petite savory, tea sandwiches, desserts, scone with Devonshire cream and a bottomless pot of tea. The relaxed pace and perfectly prepared plates are thoroughly refreshing. Tea is served at set times, and reservations are recommended. However, since this is a touristy area, walk-ins are welcome and seating times are flexible.
  • Vibrissa Brewery at 10 North Kent Street, is just a block away from the Winchester Walking Mall. The spacious, airy location was once the home of the Winchester Star newspaper. Today, it is home to a large production brewery and taproom with a full service kitchen. Offering both indoor and outdoor seating, Vibrissa is spacious and a great spot for families. PRO TIP: If the weather’s good, eat outside so the kids can play on the grassy lawn.
People sitting at covered tables and in Adirondack chairs around a fire pit with a painted wall mural backdrop at Vibrissa Beer Winchester, VA
Outdoor dining space at Vibrissa Beer

Things to do with kids in Winchester, VA

Regular readers of this blog tend to be families with kids, so when talking about things to do in Winchester, Virginia, it only makes sense to include a section on the best things to do with kids in Winchester!

Enjoy the Loudoun Street Pedestrian Mall

One of the best things to do with kids in Winchester, VA is to explore the Winchester Walking Mall. When I visited, I heard squeals of delight as kids played in the Splash Pad.

Other kids had sidewalk chalk. I think maybe their parents are pros! Happy kids drew pictures and made a hopscotch grid, while parents sat on a bench nearby, chatting as they supervised.

Other families strolled through the Loudoun Street Pedestrian Mall, window shopping. And still others enjoyed dinner outdoors at the many restaurants.

Beyond the walking mall, there are many more things to do with kids in Winchester, VA.

Shenandoah Valley Discovery Museum

The Shenandoah Valley Discovery Museum at 19 West Cork Street is just across the street from the Winchester Walking Mall. This museum is huge with each floor dedicated to its own topics.

I found the bee honeycomb display to be particularly fun! How cool would it be to crawl inside the honeycomb with a giant, stuffed bee to read a book on how honey is made?

Be sure to head up to the rooftop for great views of historic Winchester.

Museum of the Shenandoah Valley

The Museum of the Shenandoah Valley at 901 Amherst St in Winchester is a sprawling space dedicated to preserving the history and heritage of the Shenandoah Valley. It includes the Glen-Burnie House and gardens, acres of hiking trails dotted with massive art installations, and a gallery displaying historic artifacts of the region.

Gallery at the Museum of the Shenandoah Valley

Handley Regional Library

Across the street from the Loudoun Street Pedestrian Mall, the Handley Regional Library at 100 Piccadilly Street is an architectural masterpiece. Built with money bequeathed to the city to build a library, Handley Regional Library is listed on the National Register of Historic Places, and Thomas Edison considered it the most beautiful library he ever visited.

Designed to “resemble” an open book, with the central dome as the binding and each wing the open pages, the library offers activities for all ages including a relaxed children’s space with toys, computers, reading areas in a bright, open space.

To escape the rain or a hot, humid afternoon, head to the library for a self-guided tour and to enjoy a storybook or two.

George Washington’s Office Museum

Located at the corner of Cork and Braddock Streets in Old Town Winchester, Virginia, George Washington used this log office as his headquarters while building Fort Loudoun nearby. George Washington’s Office Museum is not large, but it contains a number of historic relics used by Washington, including the surveying tools he used early in his career. A colonial era cannon sits on the grounds, as well as a bronze statue of young George Washington.

Due to its historic nature, this museum is not accessible.

George Washington's Office Museum in downtown Winchester, VA

Visit a Farmer’s Market

The Shenandoah Valley is, first and foremost, is about agriculture. During the Civil War, both sides fought to control the area — both for easy transport between mountain ranges and for its rich farmland.

Today, that farming tradition continues with farmer’s markets.

Many farmer’s markets have developed into agri-tourism centers, offering pick-your-own experiences, play spaces for kids, fresh-made food with dining areas and shopping.

Two that are particularly great for kids are Marker-Miller Orchards and West Oaks Farm Market.

Marker-Miller Orchards at 3035 Cedar Creek Grade in Winchester is a pick-your-own farmer’s market and so much more. They have a large children’s play space with climbers and slides for the kids. There’s a large covered porch with rockers and picnic tables to enjoy a sweet treat like their famous apple cider doughnuts and slushies. And, they have a large indoor market offering local produce, jams, mead, baked goods, hand-crafted items and more.

Playground and orchards of Marker-Miller Farms in Winchester, VA

West Oaks Farm Market and Cafe at 4305 Middle Road in Winchester is an 11th generation farm serving the Winchester Community since the days of Lord Fairfax himself (back in the 1700s). Besides the farmer’s market, they have an onsite cafe and a play area for the kids that includes a real John Deere Combine turned into play structure and slide. Throughout the year, they host live events and festivals. Head to West Oaks Farm for a delicious lunch and let the kids run and play. It’s good old fashioned fun.

John Deere Combine turned into play structure and slide at West Oaks Farm Market in Winchester VA. Farm can be seen in background
This combine has been turned into a play structure for kids visiting West Oaks Farm Market

Enjoy Dinner and a Show at Homestead Farm

The Homestead Farm at Fruit Hill Orchard, at 2502 North Frederick Pike in Winchester, is a fifth generation family farm and agri-tourism destination.

Throughout the year, they offer a farmer’s market and bakery from products grown on the farm.

Special events make this place even more special. Their Sunflower Festival each September is popular with both locals and tourists.

Sunflower mural at Homestead Farm Market in Winchester, VA with kids running out front and a windmill.

However, they are locally famous for their Thursday night concerts on the porch! This low-key, incredibly family friendly event grows in popularity year after year. Come for dinner, which they prepare on site, and includes a meat, vegetable, potato, drink and dessert. Stay for the concert, which is a good old fashioned jam session of local strummers — guitar, banjo, bass.

Back porch at Homestead Farm with guitar and banjo players on the porch and a crowd in the yard watching the show.

The kids run free through the fields and play on the covered wagon while the band plays on stage.

Playground at Homestead Farm in Winchester, VA

There are limited picnic tables available, and they recommend you bring your own camp chair.

The night I went, heavy clouds, wind and unseasonably cold temperatures did not keep the crowd away. People brought fuzzy blankets and enjoyed the show. The rain even held off until it was over!

If you’re passing through Winchester on a road trip or you’re looking for a fun, laid back family weekend, there are plenty of things to do in Winchester, Virginia to entertain the whole family. Explore historical sites, local museums or the Winchester Walking Mall. Enjoy delicious, locally grown food at the many farmer’s markets in Winchester. And for things to do with the kids in Winchester, VA, add the Shenandoah Valley Discovery Museum to your list. This friendly destination is sure to be one your family will enjoy, whether visiting for a day or for a weekend.