Winchester History
Founded in 1744, Winchester is the oldest Virginia city west of the Blue Ridge mountains.
The rich history of this area is a long one. It was first settled by Quakers around 1732, and later became the headquarters of our nation’s first president, George Washington, during his years as a land surveyor and later when he led troops during the French and Indian War. His office at Fort Loudoun is still here and is a local museum. During the Civil War, there were many battles here and it even served as headquarters for General Stonewall Jackson and General Sheridan.
Winchester and Frederick County was once Shawnee Indian camping grounds to which Pennsylvania Quakers came to settle in 1732. The town was named Frederick Town after Frederick, father of George III of England. In 1752 the name was changed to Winchester in honor of the ancient English capital.
Winchester Features

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40+ RestaurantsVariety of Cuisines
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ArtsPottery, Live Music, Dancing, Painting
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Annual Apple Blossom FestivalTens of thousands of visitors, parades & events
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Holiday EventsChristmas, July 4, New Year’s Eve, Fireworks
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Modern AmenitiesElectronic parking, garages, bustling businesses
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Public EventsConcerts, farmers' markets, and more
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60+ Retail ShopsCoffee shops, toy stores, shoe stores & more
Latest News & Articles
Things to Do in Winchester
Check out must-see sights and activities:
Stonewall Jackson's Headquarters, Museum of the Shenandoah Valley, History Museums, Specialty Museums. For personalized recommendations, try our AI trip-planning product..
Top 10 Reasons to Move to Winchester Virginia
The area has a large up-and-coming industry along with major, established industries. The main industries are education, health and social services, manufacturing, and food processing..
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The Loudoun Street Mall is seen Monday from Cork Street. Winchester Development Services Director Shawn Hershberger said...
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This week's FOX 5 ZIP TRIP takes us to WINCHESTER! Located in the Shenandoah Valley, this vibrant town offers chances to shop, dine and explore history!
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A Winchester Virginia getaway or day trip offers tasty dining and craft beer, beautiful scenery, interesting history, and unique fun for every age...
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Read More19 Reasons Why Everyone Must Visit Virginia’s Shenandoah Valley
Geographical treasure known for its natural beauty, historic sites, and diverse outdoor activities...
Read MoreOld Town Winchester voted among best main streets in nation
The historic walking mall and nearby streets of Old Town Winchester have ranked in a nationwide poll of America’s...
Read MoreShenandoah Apple Blossom Festival
Located in Winchester, VA the Shenandoah Apple Blossom Festival includes over 40 springtime events! Fun for the whole family!
The Bloom is an annual event organized by the Shenandoah Apple Blossom Festival private organization and held in the City of Winchester and Frederick County. Attracting crowds in excess of 250,000 people, the festival includes over 10 days of events such as the Old Town Wine & Fine Arts Festival, Apple Blossom Carnival, dances, parades, band concerts, sporting events, luncheons, parties, and much more.
The Festival is held in different locations all over the City of Winchester & Frederick County Virginia, in the beautiful and historic Northern Shenandoah Valley, just 75 miles west of Washington, D.C. A small city with a rural atmosphere, Winchester is within an easy driving time from Philadelphia and Pittsburgh, PA; Baltimore, MD; and Richmond, VA.








Local Restaurants
50/50 Taphouse
We believe the best pairing is beer and burgers. With 50 taps and 50 burgers, you can pair them together as you desire.
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George's Food and Spirits
Come experience fine dining in downtown Winchester, Virginia. Enjoy the warmth and charm of a historic building once visited by George Washington.
Learn MoreEl Centro
Our menu is packed with a variety of appetizers, classic Mexican dishes, and delicious desserts. Cool off with one of our signature margaritas!
Learn MoreRoma Old Town
Wood-fired brick oven takes center-stage in this local Italian eatery, offering pizza, pasta, and more with a new level of flavor and flair.
Learn MoreUnion Jack Pub & Restaurant
Come relax with a good pint of British ale and enjoy a traditional ploughman’s lunch. Our menu features a mix of domestic and European beers, plus a variety of pub fare.
Learn MoreViolino Ristorante Italiano
We are a small fine dining restaurant specializing in traditional and authentic Italian cuisine. All of our items are made from scratch on premises from the bread to the gelato.
Learn MoreVillage Square Restaurant
Village Square Restaurant serves contemporary American cuisine with an international flair. Served in a casual dining atmosphere, we place great emphasis on great service and a comfortable setting.
Learn MoreUno Pizzeria & Grill
At Uno Pizzeria & Grill, Winchester VA, we draw our identity and inspiration from the artisan heritage of the original Pizzeria Uno in Chicago. We still make our deep dish pizza dough fresh every morning. Today, we are as passionate about craft beer as we are our pizza.
Learn MoreVIBRISSA BEER & KITCHEN
Located on historic Main Street in beautiful Front Royal, Virginia — the gateway to the Shenandoah Valley. Winchester location coming in 2022.
Learn MoreWATER STREET KITCHEN
Down-home cooking in Historic Downtown Winchester Virginia. Chef Dan Kalber's take on classic Americana cuisine, utilizing locally sourced products.
Learn MoreVIBRISSA BEER & KITCHEN
Located on historic Main Street in beautiful Front Royal, Virginia — the gateway to the Shenandoah Valley. Winchester location coming in 2022.
Learn MoreTHE AMERICAN BAR
The American Bar is inspired by the French brasserie-style restaurants styled after the "American" bars in Paris at the turn of the 20th Century, offering traditional bistro menus as well as an extensive French wine list and fantastic cocktails.
Learn MoreMACADO'S
Macado's became popular for its eclectic ambiance of cartoon, antique, and nostalgic local decor, as well as its wide array of hearty yet modestly-priced sandwiches, subs, and entrees.
Learn MorePICCADILLY BREW PUB
A historic warehouse remodeled into a restaurant and bar offering three distinct dining areas and two private event rooms.
Learn MoreSABAI THAI WINCHESTER
The journey began in 2008 when my aunt (Chef Wan) who owned and operated a Thai restaurant in Thailand for many years, together with my big sister (Nee), launched this culinary venture.
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Entertainment
Entertainment Live music, performance, events, and entertainment located in the heart of beautiful, historic downtown Winchester, VA.

Bright Box Theater
A dynamic performance venue for live music, comedy, and creative parties and celebrations..
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Blue Fox Billiards
Energetic music venue offering live acts, American restaurant, karaoke, TVs & pool tables..
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World's Away Escape
Live, interactive challenges where you & your crew have only 60 minutes to escape.
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Splash Pad
20 spray heads dance up & down. After dark, watch as the water is illuminated in bright colors.
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Backseat Bar and Grill
Get ready to rock out to the largest live music venue in the tri-state area..
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Alamo Drafthouse
State-of-the-art movie theater with a full restaurant menu and food service in each auditorium.
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First Friday
First Fridays often feature art, music, food, wine tastings, and the unique shopping of Old Town.
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