Loudoun Street Pedestrian Mall

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 […]

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 […]

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 […]

? 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 […]

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 […]

Join us in historic Old Town Winchester for a day of celebration culminating with a spectacular and FREE New Year’s Eve Neon Nights & Laser Light Show at the Old Courthouse Civil War Museum, street performers along the walking mall and the traditional Apple Drop at midnight on Wednesday, December 31, 2025, from 6:00 pm […]

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 […]

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.

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 […]