Discover a Walkable Downtown and Centuries of History in Charming Virginia Town

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This charming historical town combines the appeal of rural living with a vibrant urban center.

Located in the Shenandoah Valley , near the border of Virginia and West Virginia The border area houses Winchester, a quaint town featuring a lively pedestrian mall, picturesque rural farmers' markets, and a rich historical legacy. Offering everything from cultural attractions to artisanal brews, this outdoor enthusiast’s haven is conveniently near the Appalachian Trail as well as the scenic Lower Shenandoah River.

Below is guidance on what activities to enjoy, where to dine, where to have drinks, and where to lodge in Winchester, Virginia.

What To Do

Walk Around Historic Downtown Winchester

The core of the city is Old Town Winchester, with its Loudoun Street Pedestrian Mall serving as a hub for various boutiques and eateries. You can spend hours wandering through this area, discovering anything from a standalone bookstore to a contemporary pharmacy alongside vintage stores. Adjacent to the primary pedestrian zone, you will come across traditional outlets such as Kimberly’s, which offers apparel, items for kids, and gift options.

oldtownwinchesterva.com , Winchester, VA 22601

Attend a Performance at Winchester Little Theatre

Ensure you secure tickets if you find yourself in town when Winchester Little Theatre has a performance. Situated within an old 1895 Pennsylvania Railroad freight depot, this community theatre hosts various productions including comedies, dramas, and more all year round.

winchesterlittletheatre.org , 315 West Boscawen Street, Winchester, VA 22601

Get Outdoors

You don’t necessarily have to tackle the whole Appalachian Trail to enjoy nature. You can explore along Skyline Drive, take a walk on the Winchester Green Trail, or visit Sky Meadows State Park instead. During warmer weather, you might also want to try kayaking on the lower part of the Shenandoah River.

Select Fresh Products at a Farmstand

Nothing beats coming back from a journey with souvenirs like homemade jams, fresh vegetables, and delicious snacks. Fortunately, Frederick County, which includes Winchester, is famous for its abundant farmers' markets. If you intend to visit multiple spots, make sure to grab one Farm Explorer Passport At any of the markets to obtain stamps for visiting each one.

richardsfruitmarket.com , 6410 Midway Road, Middletown, VA 22645 westoaksfarm-market.com , 4305 Middleton Road, Winchester, VA 22602 markermillerorchards.com , 3035 Cedar Creek Grade, Winchester, VA 22602

Explore The Museum of the Shenandoah Valley

The Museum of the Shenandoah Valley showcases displays with artworks created by local talents from the valley as well as international artists. You can view exhibitions that include 123 – I love you and Contributions: Black Americans in the Shenandoah Valley , or wander through the seven acres of gardens or traverse the 90 acres of walking trails.

themsv.org , 901 Amherst Street, Winchester, Virginia 22601

Explore the Patsy Cline House and Museum

Enthusiasts of country music should make sure to visit the Patsy Cline House and Museum, which was home to Cline during her teenage years up until age 21. This unpretentious dwelling shares her personal narrative via audio tracks and memorabilia, all arranged as they would have been during her stay.

visitwinchesterva.com/locations/patsy-cline-historic-house , 608 S Kent Street, Winchester, VA 22601

Where to Dine and Imbibe

Head Over to Bonnie's Southern Market and Bakery for Morning Eats

Treat yourself to a comforting breakfast meal before embarking on your busy exploration day at Bonnie's Southern Market and Bakery, known for serving traditional morning fare alongside well-smoked BBQ options. Be sure to try their brisket with eggs to experience flavors from both categories.

winchestersbestbbq.com , 334 West Boscawen Street, Winchester, Virginia 22601

Drop by Hopscotch Coffee and Records for your caffeine boost.

As suggested by its name, Hopscotch Coffee and Records offers a refreshing blend of tunes and caffeine. It’s an ideal spot to drop in anytime during the day for your favorite cup of java. The café serves up Lone Oak Coffee, a locally roasted brand situated mere moments away from the store.

hopscotchcoffeeandrecords.com , 250 Millwood Avenue, Winchester, VA 22601

Get Lunch at Oak Stone Pizza

At Oak Stone Pizza, their wood-fired artisanal pizzas should not be missed, particularly when visiting from downtown or heading into rural areas nearby. The Smithfield Luau offers an ideal blend of traditional Hawaiian flavors with premium Virginia ham.

oakstonepizza.com , 1000 Valley Avenue, Winchester, VA 22601

Discover the Winchester Beer and Cider Trail

It’s uncommon for a beer route to offer this many close-by locations, yet downtown Winchester excels in providing an array of options for both beer and cider enthusiasts. Here you can discover microbreweries, cideries, and establishments serving up brews along with meals and even pet-friendly spaces. In all, there are six breweries plus two cideries within reach, such as Dividing Creek Beer Co., Vibrissa Beer, and Winchester Ciderworks.

winchesterbrewtrail.com , 1400 South Pleasant Valley Road, Winchester, VA 22601

Enjoy An Engaging Meal At Paladin Downtown

Downtown Paladin transforms into the go-to place on a Saturday evening, featuring lively décor, inventive cocktails, and a blend of sophisticated and traditional pub fare. If you're waiting for a table, consider settling in at the roof terrace for an appetizer cocktail instead.

paladinrestaurants.com/paladindowntown , 31 East Piccadilly Street, Winchester, VA 22601

Where To Stay

Stay At The George Washington Hotel

The historic George Washington Hotel is right in the heart of downtown, walkable to Loudoun Street, restaurants, and shopping.

wyndhamhotels.com , 103 East Piccadilly Street, Winchester, VA 22601

Related: 16 Top Activities to Enjoy in Lexington, Virginia

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