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The northwesternmost city in Virginia beckons visitors from far and wide. Located just 75 miles from Washington D.C., Winchester is an easy drive. Even at just 5.5 hours from my hometown of Durham, NC, the Shenandoah Valley calls visitors to enjoy it. So what should you do during a weekend getaway to Winchester, VA?
Whether you want to visit a small town that still has an easily walkable downtown teeming with shops and restaurants, explore breweries, learn about apples (who knew there were so many different kinds!), see historic sites, or check out the art scene, the Winchester area is for you!
Check out this perfect weekend itinerary:
Friday Night in Winchester, VA:
If this is your first time in Winchester, check into your stay at the George Washington Hotel, your home base for the weekend. This Wyndham hotel is perfectly situated to walk to all downtown Winchester sights.
Arrive in town and visit Old Town Winchester Walking Mall to find yourself dinner. I highly recommend Alesatian Brewing. Whether you opt to eat downstairs in the Roma Old Town Wood Fired Pizzeria restaurant or upstairs in the brewery, you’ll discover amazing pizza.
Stroll the pedestrian-friendly area of Old Town Winchester, shop at some of the boutiques, and check out the nightlife. This is by far one of the best things to do in Winchester!
Check out the list of Entertainment Options below to schedule your evenings or special events during your weekend getaway to Winchester, VA.
Saturday in Winchester, VA:
Start your day with a fresh cup of coffee at any of the fabulous coffee shops along Loudoun Street. Two of the best places to try are the Espresso Bar & Cafe and the Hideaway Cafe.
Take the time to explore more of downtown Winchester. Take a selfie next to the Biggest Apple roadside attraction at 135 N. Braddock Street. Right behind it, you’ll find Kimberly’s, a shop where you can find great gifts or an outfit or two. Walk across the street to take a peek inside the Handley Regional Library, a public library built in the Beaux-Art style completed in 1913.
For a fast and light lunch, stop at Gringo Gordo for a delicious empanada at an affordable price. Having lived in Argentina for four years, I appreciate an authentic Argentine empanada. With twelve flavors on hand, you’re sure to find one to suit your tastes. My favorites were the Argentine Beef and Brisket ones. Vegetarians will delight in knowing that half of the offerings are veggie options!
Spend your afternoon following Winchester’s Mural Trail, which is always one of my top picks of things to do. Or opt to spend your day on a self-guided tour of Winchester’s breweries. Visit Winchester Brew Works, which combines a mural and beer!
Stop for dinner at Vibrissa Beer & Kitchen. The newest brewery in town offers a delicious menu of both food and fresh brews. For the non-beer lovers, wine and soft drinks are also available. Use their app for quick service directly to your table. By the way, I highly recommend the fried wontons! This family-friendly brewery is the perfect dinner spot.
If you haven’t been drinking (or have a designated driver), check out the Family Drive-In Theater in neighboring Stephens City. Thanks to the fabulous weather in the Shenandoah Valley, the drive-in movie theater is usually open from April to the beginning of December.
Sunday in Winchester, VA:
Grab an early breakfast at one of the most popular places in town: the Papermill Place Restaurant. It’s the perfect place to grab a quick breakfast with a hot cup of joe.
After breakfast, make your way to the Museum of the Shenandoah Valley. What? Annick is adding a museum to her itinerary? This museum really surprised me and featured art in a unique way. Show up an hour or so before the museum opens and walk the trails where each piece of art will delight you. This is a great spot for those needing to stretch their legs.
Once the museum opens, purchase a ticket which includes the neighboring garden and Glen Burnie Historic House.
Enjoy brunch at Bonnie Blue Southern Market & Bakery. Bonnie Blue is a local favorite located in a converted gas station from 1920. No matter what you order, don’t skip a side of their breakfast potatoes. Trust me – you won’t regret it!
PRO TIP: Bonnie Blue has a line and a wait most of the time. To avoid this, visit them around 12-12:30 pm.
Tour the Patsy Cline Historic House. Born and interred in Winchester, Virginia, country music legend Patsy Cline spent some of the most stable years of her life here. The home showcases her beginnings into the music world. Songs like Crazy made her a crossover hit on both country and pop charts. Tours are held seasonally on the hour on Sundays from 1-4 pm (subject to change).
On your way out of town, stop by one of Winchester’s farm stands such as Marker Miller Orchards or Richard’s Fruit Market. Winchester is famous for its apples and apple orchards, so take a moment to pick some apples (if in season), try some cider, or enjoy an apple cider donut. One of my favorite snacks is an apple cider donut ice cream sandwich – get one!
Entertainment Options in Winchester VA
Get cultured with a performance at the Shenandoah University Conservatory.
Before your trip, check whether there are special performances at the Shenandoah University’s Conservatory at the Ohrstrom-Bryant Theater. The school’s strong emphasis on world-class entertainment means that students’ performances should not be missed. The dance performance I enjoyed featured well-known and new pieces.
Attend one of Winchester’s many festivals.
Shenandoah Apple Blossom Festival
Of course, the apple capital hosts an annual apple blossom festival! Spread over ten days, guests get to experience all kinds of events, from parades, games, live music, and food.
Lovers of Renaissance faires will delight in learning that in neighboring Clear Brook, two weekends in October transform into old times. Wear a period costume, learn about crafts in medieval times, and of course, eat a turkey leg or two. The Faire is great fun for all ages.
Garden at the Museum of the Shenandoah Valley
During the 2023 holiday season, the gardens surrounding the Museum of the Shenandoah Valley came to life with a festival of lights, which will hopefully become an annual event. MSV regularly hosts changing outdoor art events.
Explore the Outdoors
The Winchester area enjoys scenic views due to its glorious location in the Shenandoah Valley, ideally located between the Blue Ridge Mountains and the Alleghany Mountains. A 30-minute drive will take visitors to nearby Skyline Drive, a great place to visit during the leaf-peeping season.
Explore Historic Places
This area of Virginia has a rich history. History buffs can take a historical tour. The city is home to sixty-six buildings included on the National Register of Historic Places. Visitors can see Stonewall Jackson’s Headquarters, a National Historic Landmark.
Final Thoughts on a Weekend Getaway to Winchester, VA
Larger in size than some of its neighbors, Winchester, VA, offers a lot to visitors who spend the weekend. While Washington DC residents may be tempted to take a day trip to Winchester, a weekend is the best way to explore this charming town.
The apple capital has something for everyone – a bustling main street in the form of a pedestrian mall, options for art lovers, breweries and wineries, cute boutiques, and a great food scene. Schedule yourself for a weekend getaway in Winchester, Virginia, soon!
Check out these related posts:
- Winchester VA Craft Beverage Trail (map included!)
- 20+ Things to Do in Woodstock, VA
- Foodie Destination: Harrisonburg, VA
I want to thank Visit Winchester VA for hosting my visit. As always, my posts accurately reflect my experiences and opinions.
Happy travels,
Annick, The Common Traveler
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Raised as a third culture kid living in South America and Europe, Annick caught the travel bug early. As an empty-nester, Annick enjoys sharing her tips for traveling for those with champagne taste and beer budgets.