Explore Winchester

Happening Next in Winchester

Upcoming Live Music Events

Paul Anka in Winchester

 Ohrstrom-Bryant Theatre 15 Aug 2026
ART

Rodney Atkins in Winchester

 Backseat Events 24 Oct 2026
ENTERTAINMENT

Maybe It Was Winchester: An Evening with Pam Tillis

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 17 Sep 2026

View More Live Music Events

Upcoming Festivals Events

Peach Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 8 Aug 2026
FESTIVALS

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 12 Sep 2026
FESTIVALS

Dawg Days of Summer: Hot Dog Crawl

 Old Town Winchester 22 Aug 2026
FITNESS USD 18 TO 34

View More Festivals Events

Upcoming Food Truck Festivals Events

2026 Winchester Greek Festival

1700 Amherst St, Winchester, VA, United States, Virginia 22601 22 Aug 2026
FESTIVALS

Fall Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 17 Oct 2026
FESTIVALS

South African Wine and Food Festival

 Patti's Place 19 Sep 2026
FOOD-DRINKS USD 45 TO 75

View More Food Truck Festivals Events

Upcoming Music Festivals Events

Fiddles & Fifths 2026

 Shenandoah Valley Civil War Museum 12 Sep 2026
FESTIVALS

The YDC's 2026 Festival of Trees

 302 S Loudoun Street, Winchester, VA 21 Nov 2026
FESTIVALS

Apple Harvest Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 10 Oct 2026
FESTIVALS

View More Music Festivals Events

Upcoming Pop-Ups Events

Playground Pop–Up

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 30 Jul 2026
POP-UPS

FREE COMMUNITY DANCE NIGHT!

 Vibrissa Beer 26 Aug 2026
DANCE FREE

COMMUNITY DANCE NIGHT -- Still Freee!

 10 N Kent St, Winchester, VA, United States, Virginia 22601 26 Aug 2026
MEETUPS

View More Pop-Ups Events

Upcoming Comedy Events

Winchester, VA @ Bright Box Theater

 Bright Box Theater 31 Jul 2026
PARTIES

Cornhole For Charity

 Peaceful Fields Sanctuary 22 Aug 2026
FITNESS USD 7 TO 34

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

 Escutcheon Brewing Co. 14 Nov 2025
COMEDY USD 13

View More Comedy Events

Trending Events in Winchester

First Friday

 Old Town Winchester Walking Mall 7 Aug 2026
OPEN-MIC

Lebanese Wine Pairing Dinner at Byblos Winchester

 Byblos Winchester 13 Sep 2026
FITNESS USD 70 TO 95

Evening With The Babys

 The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA 31 Dec 2026
FITNESS USD 162

Sunflower Festival

 2502 N Frederick Pike, Winchester, VA 22603-4162, United States 12 Sep 2026
FESTIVALS

Raised on Truth: Struggle Jennings Live

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 10 Sep 2026
ENTERTAINMENT

Trunk or Treat on Loudoun Street

 302 S Loudoun Street, Winchester, VA 17 Oct 2026
HALLOWEEN

Country. Patriotism. ALL the Hits. - Aaron Tippin LIVE

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 11 Sep 2026
CONCERTS

Apple Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 3 Oct 2026
FESTIVALS

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026
FESTIVALS

Doyle Lawson and the Quicksilver Band

 252 Costello Drive Winchester Va. 22602 12 Sep 2026
MUSIC

16th Annual Patsy Cline Block Party

 608 South Kent Street, Winchester, VA, United States, Virginia 22601 5 Sep 2026
ENTERTAINMENT

Honeycrisp Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 5 Sep 2026
FESTIVALS

Pumpkin Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 24 Oct 2026
FESTIVALS

Celebracion of Winchester

Taylor Pavilion Winchester 19 Sep 2026
KIDS

Samhain Luna Market 2026

 125 S. Loudoun Street, Winchester, VA 31 Oct 2026
HALLOWEEN
Browse by category

More things to do in Winchester

Live Music
Festivals
Food Truck Festivals
Music Festivals
Pop-Ups
Comedy
St. Patrick's Day
Bar Crawls