A WEEKEND IN WINCHESTER, VIRGINIA

The historic town of Winchester, Virginia is a great place to spend a long weekend. Nestled in the valley of the Shenandoah River and in the shadows of the Blue Ridge Mountains, the city is famous for the being the home of Patsy Cline and for its annual Apple Blossom Festival, celebrating the long history of growing apples in the region.

Here's how we'd spend a weekend in one of our favorite cities and live like a local-

FRIDAY

STAY- You're staying in the historic George Washington Hotel. Positioned in the heart of the old town district, this century-old building surprises you with comfort and modern rooms.  From here, you'll be able to walk to everything in the downtown area.

EAT- You'll have dinner at Paladin Downtown, a lively local spot serving up southern American dishes like Bourbon & Coke Meatloaf and Skillet dishes. Reservations recommended

DRINK- After taking an evening stroll along the old town mall, as we call it, head back to the George Washington Hotel and step into Half Note, a casual cocktail lounge with great wines, beers, and cocktails and occasionally  live music.

SATURDAY

COFFEE- You've got a busy day ahead. Power up with a coffee from Doppio Bunny. A great local coffee bar with comfortable leather couches, their signature Valencian latte with orange zest is a must-try.

EAT- Drop into Knead Bread Bakery for one of their scones and breakfast sandwiches. This friendly artisan bakery is one of downtown's best-kept secrets.

SHOP- After breakfast, you're spending the morning on the old town mall, where merchants and artisans will greet you with local hospitality.  

Eugene B. Smith Gallery features the art of a local watercolor painter. His scenes of iconic local landmarks and nature views from his travels grace the homes of many locals. If you're fortunate, you might even meet the artist himself.

Time Traveler Toys and Collectibles- this place will bring back childhood memories. Chock-full of fun toys from the past, it has an incredible selection in a cozy space.

Handworks Gallery- a well-curated shop featuring handmade items from around the world. Every piece is unique and the owners are happy to share the stories of the artisans. This is one of our favorite gift shops.

SEE- Winchester is one of Virginia's oldest cities and there are 3 historic places downtown that you'll want to see.

Step into the Shenandoah Valley Civil War Museum. Housed in a former courthouse built in 1840, the story of the Winchester's role in the civil war is told through the exhibits here.

Going further back in time, around the corner is George Washington's Office museum. This log cabin from the 18th century is where our nation's first President worked and features some historical artifacts that you won't see anywhere else.

The Handley Library is a local public library within Virginia's best example of Beaux-Arts classical architecture. Inside, you'll walk up the curving staircases and view the dome and stunning stained glass close-up.

EAT- For lunch, pop over to Bonnie Blue Southern Market. In addition to the area's best smoked meats, this friendly local spot with rustic decor bakes up buttermilk biscuits that sell-out daily.

SEE- After lunch, you'll head over to the nearby Museum of the Shenandoah Valley. With an expansive collection of local history and rotating art exhibitions, this museum also features easy walking trails spanning 214 acres of green space. 

Next door is the Glen Burnie House, a brick mansion built in 1794. Take a self-guided tour through this carefully-preserved home and imagine what local life was like over two centuries ago.

DINE- For dinner, reserve a table at Antica Trattoria. Serving up authentic Sicilian food, including housemade pasta, this cozy restaurant is one that you'll remember long after your trip.

DRINK- The Wine Room at Taylor Pavilion has one of Winchester's best wine selections and an extensive selection of spirits with a speakeasy vibe. If the weather's nice, grab a seat outside and wind down from your day.

SUNDAY

COFFEE- After checking out from your hotel, a short 3-minute drive will bring you to Hopscotch Coffee & Records.  This local coffeehouse has great coffee, a global selection of whole beans, and a record shop to browse while you're drinking your cold brew.

EAT- For breakfast, you're going full local to an unassuming down-home spot. Papermill Place has a classic breakfast menu pancakes, steak & eggs, and country ham. You'll rub elbows with all types of residents while being served the best country breakfast you've ever had.

SEE- After breakfast, you'll stroll around the gardens of Abram's Delight before taking a tour of Winchester's oldest house. This stone house is a museum with guided tours, original colonial furnishings, and a reminder this lovely city has a rich history.