42 things to do in Winchester, Virginia this month
October 2026 in Winchester, Virginia brings 42 live events across the city, led by music (16), community (13), sports (8). 1 events are explicitly listed as free. Here's what's on.
Music (16)Community (13)Sports (8)Trivia & Games (4)Festival (3)
All October 2026 Events
Frequently Asked Questions
What's happening in Winchester in October 2026?
There are 42 events in Winchester, Virginia in October 2026, including Thursday On The Farm at The Homestead Farm at Fruit Hill Orchard, 2026 Watts Golf Outing at Rock Harbor Grill, First Friday with Friends of Old Town at Downtown Walking Mall, Savannah Dexter: Damage Control Tour II at Backseat Events USA. Browse the full October 2026 calendar on VenuNite.
Are there free things to do in Winchester in October 2026?
Yes — 1 October 2026 event is explicitly listed as free in Winchester. Confirm current entry details on the event page or organizer source.
How do I find events in Winchester for a specific date in October 2026?
VenuNite lists every upcoming event in Winchester, Virginia with date filters. Use the date picker on this page to narrow October 2026 down to a single day or weekend.