Welcoming visitors with warm hospitality for over 250 years, Old Town Winchester hosts over 30 restaurants, 60 shops and numerous historic sites and museums. With a beautiful pedestrian mall, shopping in Old Town Winchester is an experience to be savored.

If you’re tired of traffic and the suburbs, you will love your visit to Old Town. Come enjoy a wonderful meal on the Walking Mall; eat at an outdoor cafe and watch people stroll by or dine in a sumptuous dining room with a crackling fire. No matter the season or your dining preference, Old Town Winchester has something for you. And after your meal, visit our unique shops, enjoy a drink or an ice cream cone, stroll down shady streets, and enjoy the feeling of nostalgia here. It’s like coming home.

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.

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.