A weekend getaway or a day trip from nearby Washington, D.C, Baltimore, MD, Richmond, VA, or Harrisburg, PA to Winchester, VA, are all within a 90 minutes to less than 2½ hours of drive.
The northern Virginia city of Winchester has much to offer visitors. Spend the day, weekend, or week exploring the pedestrian mall’s shops, George Washington’s Office, the Patsy Cline Museum, breweries, and historic architectural design. You can even spend the day in nature exploring the Shenandoah Valley’s country road, trails, and farm markets. With so many things to do in Winchester VA, there’s something for everyone to enjoy!
Explore the to-do list below and make Winchester more than a stop for gas as you switch from I-81 to I-66 or vice versa. You will be surprised at how much there is to do in this beautiful Shenandoah Valley town.
How to get to Winchester
Winchester is an easy drive from almost anywhere, as it is conveniently located near Interstates 81 and 66. Unfortunately, for those without personal transportation, it can be more challenging to reach the city since Amtrak and Greyhound do not have stops directly in Winchester. The closest stops are in Harpers Ferry, MD, and Front Royal, VA, both of which are a short drive away.
The easiest way to get to Winchester is by car. From Washington, D.C., you can take I-66 west toward Front Royal, then head south on Route 522 into Winchester. If you’re traveling from Harrisburg, PA, take I-81 south for about two hours, which will take you directly into Winchester. For Baltimoreans, head west on I-70 and then take Route 340 south. Richmond residents will travel north on I-95 to Fredericksburg, then head north on Route 17 before finally taking I-66 west toward Winchester.
Downtown Places to Visit
After arriving in Winchester, head to the Winchester Fredericks County Visitors Center. Here, you can get valuable information on how to best spend your time in town. Be sure to pick up a self-guided walking tour map, check out the list of special events happening during your stay, and learn about available guided tours.
The Visitors Center also offers a short video about Winchester, giving you a great introduction to the area.
For those interested in learning more about Winchester’s role in the Civil War, the Civil War Orientation Center provides an excellent overview.
Patsy Cline fans will enjoy the Becoming Patsy Cline exhibit, which highlights the early years of the legendary singer’s life.
The Visitors Center’s patio is a lovely spot to enjoy a picnic while overlooking Rouss Spring and Jim Barnett Park.
Once you’ve gathered all the information you need, it’s time to explore Old Town Winchester!
Visit Old Town Winchester
The charming 250-year-old Old Town Winchester offers visitors delightful strolls past 60 shops to peruse, 30 delicious restaurants, fascinating museums, and stunning architecture to admire..
There’s something for everyone, with museums dedicated to Stonewall Jackson, George Washington, Patsy Cline, and the Shenandoah Valley Discovery Museum for children.
Explore the George Washington Office Museum
When searching for things to do in Winchester, a visit to the George Washington Office Museum should be at the top of your list.
This historic military office was used by George Washington for 16 months from 1755 to 1756 as he planned and oversaw the construction of Fort Loudoun. As you tour the museum, you’ll learn about his time in Winchester and view personal artifacts, including some of his surveying equipment and even a lock of his hair. Outside the museum, you can also find a cannon from Fort Loudoun.
Visit the Handley Library and Marvel at the Architecture
Just a block off the pedestrian mall, the Handley Regional Library sits. Step back and admire the design of the central rotunda, flanked by wings on each side. Built in the Beaux-Arts Classicism style, the library’s architecture resembles an open book. Can you see the dome as the spine, with the wings representing the book’s cover and pages?
Mount Hebron Cemetery
The Mount Hebron Cemetery is a fascinating destination in Winchester, with over 30,000 graves dating back to the 1760s, surrounding the historic Lutheran Church.
In the Stonewall Confederate Cemetery section, you’ll find the graves of more than 2,500 Confederate soldiers who died in the Winchester area.
Another section of the cemetery features graves from the late 18th century. Among the notable figures buried here are Confederate General Turner Ashby, library benefactor John Handley, and former Virginia governors Harry Byrd and Frederick Holliday.
The drive through the cemetery’s rolling fields is both peaceful and picturesque. If you’re looking for a quiet place to sit and reflect, the labyrinth offers a serene spot for contemplation.
Old Town Pedestrian Mall
The two-block Old Town Pedestrian Mall on Loudoun Street offers plenty to explore along its charming brick streets.
In addition to the shops, restaurants, and museums, the kids will need a change of clothes in the summertime after enjoying the Splash Pad at the southern end of the mall.
If you’re in town on the first Friday of the month, take part in the First Fridays Celebrations of the Arts, , where you can meet local artists and watch live demonstrations. During the summer, you’ll also find fresh fruits and vegetables at the Farmers Market. Plus, the Apple Blossom and Wine & Fine Art Festivals take place here every May.
For the best shopping deals, visit on Friday or Saturday. However, if you’re looking for a quieter experience, Sunday is the perfect time for a peaceful stroll.
Patsy Cline Historic House
Explore musical history at the Patsy Cline Historic House, located just half a mile from the mall. Country music legend Patsy Cline lived in this modest Winchester home from the age of 16 until she was 21.
Patsy Cline was one of the most influential singers of the 20th century, known for her successful crossover from country music to pop.
Shenandoah Valley Discovery Museum
The Shenandoah Valley Discovery Museum is one of the best attractions in Winchester for kids. With 19,000 square feet of fun, interactive exhibits spread across four floors, it’s an experience the whole family will enjoy.
When you need a break, head to the rooftop level for stunning views of Winchester.
Tour Stonewall Jackson Headquarters
The historic Hudson River Gothic Revival-style house on Braddock Street is a must-visit in Winchester.
As you tour Stonewall Jackson’s 1861-1862 Civil War headquarters, you’ll see Jackson’s prayer table and prayer book, along with family artifacts. You’ll also get a glimpse of what his office would have looked like during his time there.
Take Part in the Apple Blossom Festival
Attending the Apple Blossom Festival in Old Town is one of Winchester’s top activities, drawing nearly 250,000 visitors each year.
The spring festival lasts for six days, giving you plenty of opportunities to return and enjoy all that it offers.
Explore the booths of local crafters and artisans, bring a lawn chair or blanket, and tap your toes to live local entertainment. Don’t forget to sample some of the delicious festival food from the various concessions.
One of the festival’s main highlights is the Old Town Wine and Fine Arts Festival. Taste Virginia’s finest wines, and be sure to pick up a bottle or two of your favorites to take home.
After the festival, take a scenic drive along Cedar Creek Grade, Barley Lane, Middle Road, and Marlboro Road to view the fragrant apple blossoms set against the backdrop of the Blue Ridge Mountains.
Places outside of Town to Visit
Explore the Abrams Creek Wetlands Preserve
Just a 10-minute drive from Winchester, the 25-acre Abrams Creek Wetlands Preserve offers a peaceful retreat into nature. Bike or stroll along the mile-long interpretive trail, where you’ll encounter over 300 plant species and have the chance to spot 180 species of birds. If you’re lucky, you might also see muskrats, painted turtles, and mink.
Stroll Through the Museum of the Shenandoah Valley
Located just a 30-minute walk or 5-minute drive from Old Town, the Museum of the Shenandoah Valley is a must-visit for anyone exploring Winchester.
Take time to explore the house, museum, and gardens. As you wander through the beautiful gardens, you’ll learn more about the region and its people. Be sure to visit the Asian-influenced water garden and the stunning Glen Burnie Gardens.
Don’t miss the Shenandoah Valley, Founders, and R. Lee Taylor Miniatures Galleries on the museum’s second floor. The Shenandoah Valley Gallery explores the valley’s history and features rotating exhibits of local decorative arts. The Founders Gallery showcases impressive American and European decorative and fine arts.
Discover the State Arboretum of Virginia, Blandy Experimental Farm
Explore the Virginia Native Plant Trail and winding paths throughout the 172-acre State Arboretum of Virginia. This vast space is home to 5,000 woody trees and shrubs from around the world, including one-third of the world’s species of pines, a grove of 300 ginkgo trees, and a Lebanon alley. Don’t miss the herb garden, which is a tranquil spot to relax and reflect.
Shop at a Winchester Farm
Just a short scenic drive from town, enjoy delicious fruit, fresh produce, and sweet treats at local farms.
Marker-Miller Orchards and Farm Market features an incredible on-site bakery where you can indulge in delicious apple cider donuts. The kids will enjoy the playground, and you can snap a fun photo by the giant apple sculpture near the parking area.
The Homestead Farm at Fruit Hill Orchard, while smaller, boasts a beautiful organic garden, a gift shop, and delicious gluten-free and sugar-free baked goods. Visit on a Thursday evening from mid-August to early November for free bluegrass music.
In late September, don’t miss the Sunflower Festival at Homestead Farm, where you can enjoy free music, food, crafts, and plenty of sunflowers to admire.
Old Town Farmer’s Market
If you’re in town from May to September, be sure to visit the Old Town Farmer’s Market at the Taylor Pavilion. Every Saturday, you’ll find fresh vegetables, local fruit, and incredible baked goods to enjoy while you explore the market.
Where to Eat in Winchester Virginia
While in Winchester, eat at one or more of the excellent locally owned and operated restaurants in town. Below are a few favorites.
During your stroll around the Pedestrian Mall, stop in at Oak Stone Pizza for a delicious brick oven pizza. If you have a taste for fish and chips, stop in at Union Jack Pub and Restaurant, or for a romantic Italian dinner, visit Violino.
For a hearty breakfast of omelets, shrimp and grits, or their amazing biscuits and gravy, visit Bonnie’s Southern Kitchen and Bakery or Big L’s Bagels for a bacon, egg, and cheese everything bagel and a cup of coffee. For those with time to sit and relax while enjoying their cup of coffee with a Cowbell buttermilk banana cake, head to Hopscotch Coffee and Records.
When dessert is what you need, then order a Madagascar Vanilla Bean Cheesecake with caramelized bananas from Village Square Restaurant, or head to Frenchies Frozen Yogurt Lounge for a cone or cup of refreshing frozen yogurt.
Local Craft Beer and Wineries to Visit
At the Pedestrian Mall, head to the second floor, where you will find ten of Alesatian Brewing Company’s craft beers on tap, ranging from amber, Belgian, and blonde ale to IPA and lagers.
Just down the street is the Winchester Brew Works, where they have 12 beers on tap, and you are welcome to bring your food and sit either inside at the bar or outside on the pet-friendly patio.
After going to the Apple Blossom Festival, picking apples in the fall, or just passing all those apple orchards around Winchester, you may have a taste for cider. Winchester Ciderworks produces six signature, English barrel-aged, and specialty ciders, all from the local Frederick County apples at their Frederick Pike location. Stop in and try one of their fermented apple drinks.
In the middle of the vineyards and apple orchards, you will find the James Charles Winery that the Bogaty family founded in 2015. Stop in and participate in the 30-minute Classic Tasting, where you get to enjoy all their currently available white and red wines.
They have Fire Pits throughout the winter months, where you can sit around and enjoy some James Charles wine. For a romantic evening, reserve a 1-hour Table Experience where you will enjoy views of the Shenandoah Valley as you savor wines paired with spectacular food.
Winchester VA Hotels
For the average family and travelers who just want a modest hotel room, the Sleep Inn and Suites Winchester and the SpringHill Suites Winchester are great options with complimentary breakfast and pools.
Around the corner from the pedestrian mall, the George Washington Hotel in the Georgian Revival brick building is both elegant and comfortable. The hotel offers a spa, saltwater pool, and an on-site restaurant and bar.
Ten miles east of town, the Historic Rosemont Manor offers luxury rooms on spectacularly manicured lawns. If you stay here, be sure to go to one of their traditional English teas.
