First Friday
October 2 @ 5:00 pm - 9:00 pm
Free
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
- Vendors throughout the Walking Mall
- Specials and extended hours from downtown businesses
- Family-friendly activities
- DORA drinks throughout Old Town
Whether you’re grabbing dinner, shopping local, meeting friends for drinks, or just wandering downtown, First Fridays are all about giving people another reason to stay a little longer and experience everything Old Town has to offer.
2026 First Friday Dates:
- June 5
- July 3
- August 7
- September 4
- October 2
Event runs from 5–10 PM.
Music and programming may vary each month.
Presented by Friends of Old Town and sponsored by First Bank.
