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Winchester is the northwesternmost independent city in the Commonwealth of Virginia, United States. It is the county seat of Frederick County, although the two are separate jurisdictions. As of the 2020 census, the city's population was 28,120.
Things to Do in Winchester, Virginia: See Tripadvisor's 29,063 traveler reviews and photos of Winchester tourist attractions. Find what to do today, this weekend, or in July. We have reviews of the best places to see in Winchester. Visit top-rated & must-see attractions.
- The top attractions to visit in Winchester are: Rocking S Ranch Museum of the Shenandoah Valley Stonewall Jackson's Headquarters Patsy Cline Histor...
- The best outdoor activities in Winchester according to Tripadvisor travelers are: Jim Barnett Park Abrams Creek Wetlands Preserve Shawnee Springs P...
- The most popular things to do in Winchester with kids according to Tripadvisor travelers are: Rocking S Ranch Museum of the Shenandoah Valley Handl...
Sitting at the northernmost corner of Virginia in the Shenandoah Valley, Winchester offers visitors the chance to explore historical sites, museums, vineyards, farmers' markets, and tree-lined Old Town streets once wandered by the likes of George Washington and Stonewall Jackson.
- We recommend staying at one of the most popular hotels in Winchester, which include: The George Washington, a Wyndham Grand HotelCountry Inn & Suit...
- Some of the most popular restaurants in Winchester include: Taqueria GuadalajaraBonnie BlueViolino Ristorante ItalianoRoma Old Town Wood-Fired Pizz...
- Winchester is known for some of its popular attractions, which include: Old Town Winchester Walking MallRocking S RanchMuseum of the Shenandoah Val...
- If you're a more budget-conscious traveler, then you may want to consider traveling to Winchester between December and February, when hotel prices...
- Break some sweat at Jefferson Street Trail Head. Editor's Note: There's no photo available at the time of writing. Jefferson Street Trail Head serves as one of the entry points of The Trails at the Museum of the Shenandoah Valley, which covers 90 acres (36.42 hectares) of land area.
- Taste craft beers at Broken Window Brewing Company. Editor's Note: Photo taken from the establishment's official social account. Posted by Broken Window Brewing Co.
- Catch majestic live performances at Bright Box Theater. Situated at the heart of the city, Bright Box Theater serves as one of the primary event venues in the area.
- Reconnect with nature at Abrams Creek Wetlands Preserve. Editor's Note: Photo taken from the establishment's official social account. Posted by Winchester VA Parks and Recreation on Tuesday, October 8, 2019.
- History of Winchester, Virginia
- Where to Stay in Winchester
- Things to Do in Winchester, Virginia
- Things to Do Near Winchester
- Where to Go Next After Visiting Winchester
With a long history of Native American settlement on the lands, the city known as today’s Winchester was first known as Fredrick Town in the 1730s. An immigrant from Winchester, England, Colonel James Wood was the town’s first court clerk and instrumental in its establishment–and the town was later renamed after his birthplace. And, a young George ...
In the Old Town – There’s a reason why everyone loves the George Washington Hotel (Booking | Hotels | TripAdvisor). Only a block away from the heart of historic downtown Winchester on East Piccadil...
Tour the Old Town
From walking tours to food tours and Civil War tours, you’re sure to find a walking tour of Old Town Winchester. Check out the Visit Winchester websitefor more information, and call ahead to book the specific tour you want to take.
Check out the Shenandoah Valley Civil War Museum in the old Fredrick County Courthouse
Another one of the best Winchester VA things to do is visit the Shenandoah Valley Civil War Museum. It’s housed in the old Frederick County Court House right in the center of North Loudoun Street, built in 1840. The building was used as a hospital, prison, and barracks for both Union and Confederate soldiers during the war. Head inside the museum to visit a restored version of the courtroom, wall drawings left by soldiers, and a collection of artifacts and exhibits dedicated to Shenandoah Val...
Grab a bite at the old Union Bank building
Once home to the Union Bank in a Victorian-era Revival style building, today, you can find Union Jack Pub & Restaurant occupying the space, a great casual restaurant also on North Loudoun Street. They even have ax-throwing now!
Head outside of town for the wineries
While you can cross the border into West Virginia or Maryland, there are over 20 vineyards within 30 minutes of Winchester, making this a great place to explore wine tasting. Not affiliated with the make-up influencer, James Charles Winery & Vineyardis found just on the outskirts of town. Ancestors of the Bogaty family immigrated from Italy and brought their winemaking tradition with them, which they now share with the Winchester community. In Stephens City, you’ll find Valerie Hill Vineyard...
Visit the Woodrow Wilson Presidential Library and Museum
Like Franklin D. Roosevelt Presidential Library and Museum located in Poughkeepsie, New York, the Woodrow Wilson Presidential Library and Museum is found close to Winchester points of interest in nearby Staunton, Virginia. Born in Staunton in 1856, you can find Wilson’s Presidential Library in his childhood birthplace. Take a tour of the building to learn about life in the mid-to-late 19th-century. Tour the galleries to see artifacts like his famous restored 1919 Pierce-Arrow limousine, weapo...
Find your inner history buff at the Frontier Culture Museum
Just like Colonial Williamsburg in Williamsburg, VA, the Frontier Culture Museum in Staunton, Virginia is also living history museum dedicated to what life was like for immigrants from the Old World to the United States. The museum showcases the differences between life on 18th and 19th-century American farms versus those found in West Africa, England, Ireland, and Germany. They also have a Native American exhibit, an early American schoolhouse, an 18th-century Irish forge, where historic re-...
There are so many great places to visit once you’ve enjoyed all the cultural activities in Winchester! If none of these interest you, I have a whole guide on the best one day trips in Virginia. You’re bound to find some great ideas on where to go next.
Feb 3, 2023 · This small city in the north of the state is the favorite weekend escape of many people in Washington DC for good reason! From great food to historic finds, craft breweries to rolling vineyards, and outdoor pursuits to unique museums, Winchester is the perfect place to unwind.
Sep 4, 2019 · Winchester is a small town located in the Shenandoah Valley region of Virginia with charming shops, unique restaurants, historic architecture and landmarks, and a wide variety of recreation opportunities within an easy drive.
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