Help us raise funds to benefit the people, places, and passions of Winchester during our inaugural spin-a-thon! Join us on Saturday, February 22, at Valley Health Wellness and Fitness Center for a memorable Winchester-themed spin class with the one and only Penny Torian! You can join the team today and help us raise money to […]
Bring the family to Old Town Winchester for a safe and festive afternoon of trick-or-treating! Local merchants along the Loudoun Street Pedestrian Mall will be handing out candy and goodies to children in costume. Stroll through downtown, show off your Halloween spirit, and enjoy the seasonal decorations, shops, and restaurants that make Old Town such […]
Winchester’s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket — all benefiting Katie’s Comfort House.
Hop aboard the sweetest stroll in Old Town! On Saturday, December 13, our shops turn into cookie stations — each with a festive treat waiting just for you. Wander the bricks, collect cookies (while they last!), and enjoy a little holiday magic at every stop. All Cookie Crawl boxes will be picked up at Blue […]
Old Town on the Rocks January 16–18, 2026 | Old Town Winchester Old Town on the Rocks is a weekend-long bourbon and cocktail competition celebrating the creativity of Old Town […]
🍫 Chocolate Escape is coming to Old Town Winchester on Saturday, February 7th! Treat yourself (and your friends) to a sweet stroll through downtown with chocolates, treats, and fun surprises […]
Rhythm & Roots Night A Black History Month Celebration in Old Town Join us for an evening of music, culture, and community as we celebrate Black History Month with Rhythm […]
Join us for an evening of creativity, expression, and community at Art & Spoken Word Night at Typewriter Studio. As part of Black History Month in Old Town, this event will spotlight local artists, poets, and performers sharing work that reflects culture, history, identity, and lived experience. From powerful spoken word to visual art and […]
Spin to Win-Chester 🚴♂️🔥 Think you’ve got what it takes? Spin to Win-Chester is a high-energy spin-a-thon where riders compete, fundraise, and push themselves—all in support of Old Town Winchester. Join us Saturday, February 21 at Valley Health Wellness & Fitness Center for a Winchester-themed ride led by Pam Lambert. Choose Your Challenge Beginner Ride: […]
Join us for a meaningful and memorable evening as we celebrate Black History Month with History & Cocktails Night at Bright Box Theater. This relaxed, intimate event will feature short talks and local storytellers sharing stories that highlight Black history in Winchester and the surrounding region. It’s a chance to connect with our community’s past […]
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.
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