This historic town blends a countryside charm with a bustling downtown.

Located in the Shenandoah Valley, close to the Virginia and West Virginia border, Winchester is a small town with a bustling pedestrian mall, charming rural farm markets, and centuries of history. Whether you're looking for culture or craft beer, you'll find it in this outdoorsy locale that is close to both the Appalachian Trail and the lower Shenandoah River.

Here's what to do, where to eat, where to drink, and where to stay in Winchester, Virginia.

What To Do

Stroll Through Old Town Winchester

Old Town Winchester is the heart of the city, and its Loudoun Street Pedestrian Mall is where you'll find an array of small shops and restaurants. Spend an afternoon exploring everything from an independent book store to a modern day apothecary to antique shops. Just off the main pedestrian mall, you'll find classic shops like Kimberly's, a shop for clothing, children, and gifts.

Catch A Show Winchester Little Theatre

Make sure to grab tickets if you happen to be in town for a show at Winchester Little Theatre. This community theater lives in a circa 1895 Pennsylvania Railroad freight station and puts on comedies, dramas, and other entertainment throughout the year.

Get Outdoors

You don't have to hike the entire Appalachian Trail to get a taste of the outdoors. Explore the sites off of Skyline Drive, hike the Winchester Green Trail, or check out the Sky Meadows State Park. There's also kayaking on the lower Shenandoah River in the warmer months.

Pick Up Fresh Goods At A Farm Stand

There's nothing better than heading home from a trip with goodies, including local jams, veggies, and treats. And, luckily, Frederick County, where Winchester is located, is known for its fruitful farm stands. If you plan on visiting several, pick up a Farm Explorer Passport at any of the markets to get stamps for visiting each one.

Visit The Museum Of The Shenandoah Valley

The Museum of the Shenandoah Valley has exhibitions featuring artists both from the valley and around the world. Catch exhibits including 123 – I love you and Contributions: African Americans in the Shenandoah Valley, or explore the seven acres of gardens or 90 acres of walking trails.

Take A Tour of the Patsy Cline House and Museum

Country music fans will want to plan a stop by the Patsy Cline House and Museum, where Cline lived from the ages of 16 to 21. The modest house tells the story of her life through recordings and artifacts, and is decorated to reflect the time period when she would have resided there.

Where To Eat & Drink

Fill Up For Breakfast at Bonnie's Southern Market and Bakery

Indulge in a comfort food breakfast before a busy day of exploring at Bonnie's Southern Market and Bakery, where you'll find both classic breakfast dishes and perfectly smoked barbecue. Get the brisket and eggs for a taste of both.

Stop in Hopscotch Coffee and Records for a Caffeine Fix

Just as the name would imply, you'll find a cool music and coffee vibe at Hopscotch Coffee and Records, which is the perfect place to pop in for a cup of joe morning or afternoon. They brew Lone Oak Coffee, which is a local roaster located just minutes from the shop.

Grab Lunch at Oak Stone Pizza

The wood-fired craft pizzas at Oak Stone Pizza are a can't miss, especially if you're looking for a stop in between exploring downtown and getting out to the country. Try the Smithfield Luau for the perfect combination of a Hawaiian pizza and classic Virginia ham.

Explore the Winchester Beer and Cider Trail

Rarely does a beer trail have so many stops in walking distance, but downtown Winchester delivers when it comes to beer and cider. You'll find microbreweries, cideries, and breweries that also serve food and welcome dogs. There are six breweries and two cideries total, including Dividing Creek Beer Co., Vibrissa Beer, and Winchester Ciderworks.

Sit Down For A Lively Dinner At Paladin Downtown

Paladin Downtown is the hot spot on a Saturday night, with vibrant decor, creative cocktails, and a mix of upscale and classic bar food. Grab a seat on the rooftop for a pre-dinner drink if you have to wait for a table.