Small Town Love: The Top Things to Do in Winchester

A visit to Winchester offers a mix of old and new: Civil War landmarks and historic homes — including one belonging to Winchester native and country music legend Patsy Cline — sit alongside contemporary galleries, craft breweries, and shops. The Shenandoah city is also home to the Apple Blossom Festival each spring, as well as farms and orchards in the surrounding countryside.

Here’s what to do during a visit to this dynamic Shenandoah Valley town.

Museums & Gardens

Start your stay with a visit to the Museum of the Shenandoah Valley. Here, you’ll find the historic Glen Burnie House, which dates back to 1794 and is surrounded by seven acres of formal gardens to stroll. The galleries are home to works by Shenandoah Valley artists and a unique collection of miniature houses. More than three miles of walking trails crisscross the museum’s 90 acres, and visitors are welcome to explore the property year-round.

Around ten minutes from that site is Abram’s Delight Museum. The property is actually Winchester’s oldest home, built in 1754. During a visit to the main house and the 18th-century log cabin on the property, you’ll learn about what life was like for the Shenandoah Valley’s settlers.

Out & About in Old Town

Head to Old Town Winchester, the town’s more than 250-year-old market area, for an afternoon. Stop by Cork Street Tavern, where salads, sandwiches, and burgers are served up in a historic 1830s building. From here, history and architecture buffs can take a self-guided walking tour to sites throughout Old Town. Don't miss George Washington’s Office Museum, the Beaux Arts Handley Regional Library, and the Georgian-Revival George Washington Hotel

Note: If you’re planning a trip in the late fall or winter, be sure to check the historic site and museum websites before visiting, as many close during the off-season.

Spend the afternoon strolling the shops of Old Town’s Loudoun Street Pedestrian Mall. Browse the titles at Winchester Book Gallery, pick up essentials for outdoor adventures at Mountain Trails, and pop into Red Fox Creamery for a scoop of homemade ice cream.

Wind down the day with a tasting flight of craft beer at Winchester Brew Works, then head to dinner at Union Jack Pub & Restaurant, housed in the Victorian-era Union Bank Building. For an evening out, check the performance calendars at The Monument and the Bright Box Theater, a pair of Old Town venues known to host live music and comedy acts.

Battlefields & BBQ

Begin the day with a big breakfast at Bonnie's Southern Market & Bakery, which serves up hearty dishes like pulled pork and eggs, biscuits and gravy, and shrimp and grits in a historic Esso station.

Next, head to the Civil War Orientation Center inside the Winchester-Frederick County Visitors Center. There, you'll get an overview of the Shenandoah Valley Battlefields National Historic District, where many key conflicts in the war took place. You’ll find self-guided audio and driving tours to several Winchester sites, including Kernstown Battlefield and Third Winchester Battlefield.

Drive south for a self-guided tour through Cedar Creek and Belle Grove National Historic Park, where the Battle of Cedar Creek took place, a pivotal moment in the Civil War which secured Union control of the Shenandoah Valley and assisted in the reelection of Abraham Lincoln.

When hunger strikes, head to Shaffer's BBQ, a Middletown institution for smoked meat and fried chicken.

Patsy Cline & Cider

Make a visit to the Patsy Cline Historic House. The legendary country music singer was born in Winchester and resided in the home from the age of 16 until she was 21. Today, guides offer visitors an overview of her career and life at the preserved home. Fans can also take a self-guided driving tour to other places around Winchester associated with Cline.

Bonus: Plan a visit over Labor Day and you can celebrate the singer at the annual Patsy Cline Block Party.

The Apple Blossom Festival is an annual event that draws visitors to Winchester, but there are plenty of orchards and farm markets to explore even if you’re not visiting “The Apple Capital” during festival days. Marker-Miller Orchards Farm Market sells several varieties of apples, as well as baked goods like apple cider donuts, and offers pick-your-own visits to their orchards at certain times throughout the year.

The Homestead Farm at Fruit Hill Orchard and Virginia Farm Market also offer goodies like apple dumplings and apple pie, while visitors can stay the night at The Herd's Inn at Hedgebrook Farm, a working dairy farm operating since 1907. Winchester’s apples also produce top notch cider, which can be sampled in the tasting rooms at Winchester Ciderworks and Old Town Cidery.
 

Where to Stay in Winchester

• Candy Hill Campground

• Fuller House Inn and Cottage

• The Herd's Inn

• Wyndham George Washington