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 […]
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. […]
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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