Looking for a pleasant diversion from your routine? Weekdays and weekends, Winchester’s slate of entertainment options is full. Beyond the cultural, historic, and recreational events that regularly delight residents, the same area attractions that annually draw tens of thousands of tourists to the region also enchant those who live here.
SAMPLE OF ENTERTAINMENT & EVENT OPTIONS
- Apple Harvest Festival
- >Bluemont Summer Concert Series
- Blues House Street Festival
- Christmas in Old Town
- Cinco de Mayo Festival
- Civil War battlefields
- Concern Hotline’s Fish Fry
- Dinosaur Land
- Dalke’s Family Drive-In
- Doo Dah Day
- Follow the Apple Trail
- Friday Night Cheers
- Halloween Spooktacular
- Hot Air Balloon Festival
- Kite-Flying Frenzy
- Marker-Miller Orchard’s Peach Festival
- Master Gardeners
- New Year’s Eve’s First Night Winchester
- Of Ale & History Festival
- Shenandoah Apple Blossom Festival
- Shenandoah Valley Discovery Museum
- Soapbox Derby
- Winchester Exchange Club’s Chili Cook-Off






