This charming historical town combines the appeal of the countryside with a vibrant city 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. No matter whether you seek cultural experiences or artisanal brews, you can discover them all in this outdoor-friendly setting near the Appalachian Trail and the southern part of the Shenandoah River.
Below is your guide for activities, dining options, drinking spots, and accommodations in Winchester, Virginia.
What To Do
Walk Around Historic Downtown Winchester
Downtown Winchester’s core is Old Town, which features the Loudoun Street Pedestrian Mall—a hub for various boutiques and eateries. You can spend hours wandering around, discovering anything from a standalone bookstore to a contemporary pharmacy alongside thrift stores. Nearby the primary pedestrian zone, you will come across traditional outlets such as Kimberly’s, offering apparel, items for kids, and presents.
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. This local theater occupies an old Pennsylvania Railroad freight depot from around 1895 and stages comedies, dramas, and various shows all year long.
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.
Choose Fresh Products at a Farmer’s Stall
Nothing beats returning 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. Should you decide to visit multiple spots, consider picking up a
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 valley artists as well as those hailing from across the globe. Visitors can enjoy exhibitions that include
123 – I love you
and
Contributions: Black Americans in the Shenandoah Valley
, or wander through the seven acres of gardens or stroll across 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, where she called home between the ages of 16 and 21. This unassuming dwelling offers insights into her life via audio clips and memorabilia, all arranged as they would have been during her residency.
visitwinchesterva.com/locations/patsy-cline-historic-house
, 608 S Kent Street, Winchester, VA 22601
Where to Dine & Imbibe
Stop By for Breakfast at Bonnie’s Southern Market and Bakery
Treat yourself to a comforting breakfast meal before your packed day of discovery at Bonnie’s Southern Market and Bakery, known for its traditional morning fare and deliciously smoked BBQ. Be sure to try their brisket with eggs to experience flavors from each menu item.
winchestersbestbbq.com
, 334 West Boscawen Street, Winchester, VA 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 by anytime during the day for your favorite cup of Joe. The café serves up coffee sourced from Lone Oak Coffee, a nearby local roaster situated mere moments away from the store.
hopscotchcoffeeandrecords.com
, 250 Millwood Ave, Winchester, VA 22601
Grab Lunch at Oak Stone Pizza
At Oak Stone Pizza, their wood-fired artisanal pizzas shouldn’t be missed, particularly when you’re transitioning from urban exploration downtown to leisurely countryside outings. The Smithfield Luau offers an ideal blend of tropical Hawaii-inspired flavors with traditional Virginia-style cured ham.
oakstonepizza.com
, 1000 Valley Avenue, Winchester, VA 22601
Discover the Winchester Beer and Cider Trail
It’s not often you’ll come across a beer trail with this concentration of accessible spots, yet downtown Winchester excels in offering numerous options for both beer and cider enthusiasts. Here, you can discover microbreweries, cideries, and establishments that brew their own beers as well as provide dining services and pet-friendly environments. Altogether, there are six breweries along with two cideries, 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, innovative cocktails, and an array of both sophisticated and traditional pub fare. If you’re waiting for a table, consider settling in at the roof terrace for a cocktail before dinner.
paladinrestaurants.com/paladindowntown
, 31 E Piccadilly Street, Winchester, VA 22601
Where To Stay
Reside at The George Washington Hotel
The historic George Washington Hotel is centrally located in downtown, within walking distance to Loudoun Street, eateries, and shops.
wyndhamhotels.com
, 103 East Piccadilly Street, Winchester, VA 22601
Related:
16 Top Activities to Enjoy in Lexington, Virginia
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