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 Winchester’s bars, restaurants, and bartenders. There’s no entry fee — guests simply purchase featured cocktails directly from participating locations while visiting Old Town.Each stop will […]
? 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 at participating Old Town businesses all day long. It’s the perfect excuse to shop local and enjoy a little winter fun in Old Town. A […]
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 & Roots Night at Bistro SOJO. This special gathering will honor the rich musical legacy and cultural influence of Black artists through an atmosphere filled […]
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 […]
Hark and gather, ye merry souls! On Saturday, March 14th, Old Town shall be awash in music, mirth, and Celtic cheer as we proclaim a grand celebration — Celtic Fest! From the twelfth hour ‘til five of the clock, the Walking Mall shall be transformed into a lively festival village. Those who wander through shall […]
Friday nights are back in Old Town Winchester. Join Friends of Old Town for First Fridays, a monthly community celebration bringing live music, local artists, vendors, pop-ups, food, shopping, and extended downtown energy to the Walking Mall throughout the summer and fall. Each First Friday features: Live music at Taylor Pavilion Local artists and makers […]
KidzFest is returning to Old Town Winchester on Saturday, June 13 for an afternoon full of family-friendly fun, activities, entertainment, and community programming throughout the Walking Mall. Hosted by Friends of Old Town and presented by Rise Orthodontic Studio, KidzFest brings together local businesses, organizations, vendors, performers, and activity stations designed to create an interactive […]
Friday nights are back in Old Town Winchester. Join Friends of Old Town for First Fridays, a monthly community celebration bringing live music, local artists, vendors, pop-ups, food, shopping, and […]
Celebrate 250 years of history, community, and Virginia pride at the Old Town Jubilee! Enjoy a full day of local vendors, food, family-friendly activities, and live entertainment throughout historic Old Town. Gather at the Taylor Pavilion for live performances by Rebecca Porter and Melissa and the Mothmen, then cap off the evening with a spectacular […]
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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