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 […]
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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