Let's Be Friends
In Old Town Winchester
Welcome to Old Town Winchester—where history, charm, and a vibrant community come together in the heart of the Shenandoah Valley. Locally owned shops, cozy restaurants, craft breweries, and inviting coffee spots make this downtown district the place to be. With new adventures and events happening all the time, there’s always something fun to explore
The History of Us tour is here!
Take a stroll through downtown and discover the stories behind the buildings, businesses, and people who shaped it. Just scan the QR codes in the windows to explore photos and memories—right from your phone!
Get Friendly
Won't You Be Our Neighbor?
Spend an evening with friends enjoying live music at one of our local breweries, catch an unforgettable show at Bright Box Theater, or make memories with your family at the Shenandoah Valley Discovery Museum. Love the great outdoors? Take a leisurely stroll down the car-free Loudoun Street Mall, unwind in one of our scenic parks, or explore the public art installations scattered throughout downtown. Feeling festive? Don’t miss one of our seasonal events, like holiday parades, art festivals, or live performances on the pedestrian mall. Why wait? Join us in Old Town Winchester and discover what makes it so special—we can’t wait to call you a friend!
Current Projects
01
Taylor Pavilion Revitalization Project
We’re transforming Taylor Pavilion into a vibrant, community-focused gathering space in the heart of Old Town. This multi-phase project will enhance live entertainment, support small businesses, and refresh the alleyway to create a welcoming public space for years to come—all while honoring Old Town’s historic character.
02
Main Street Masterpieces
Main Street Masterpieces turns vacant storefront windows into curated art displays by local and regional artists. By activating empty spaces with creativity, the program brings new energy to the mall, supports artists, and invites visitors to explore more of Old Town.
03
History Of Us
Explore Old Town at your own pace with self-guided walking tours that share the stories behind our historic buildings and the people and businesses who shaped them.
Join us as a volunteer, sponsor, or event participant! There’s a place for everyone at Friends of Old Town, whether you’re looking to share your time, talent, or ideas.
Subscribe
Get latest news & events details
[mc4wp_form id=136]
Friends of Old Town celebrates and enhances Old Town Winchester through local events, public art, and design projects. We work with residents, businesses, and visitors to keep our historic town vibrant, creative, and welcoming for everyone to enjoy.
© 2025 Friends of Old Town
Designed by Web Strategies.