Winchester Festivals Events
Festivals Happening Next in Winchester, VA
Valley Health 10K Race
John Handley High School
2 May 2026
SPORTS
2026 Apple Blossom Grand Feature Parade Seats - Troop 9
Market Street United Methodist
2 May 2026
FESTIVALS
USD 13 TO 15
Malloy Toyota Country Music Party
James R. Wilkins, Jr. Athletic & Events Center
2 May 2026
COUNTRY-MUSIC-FESTIVALS
Contemporary Christian Concert presented by Clean Water of Virginia
James R. Wilkins, Jr. Athletic & Events Center
3 May 2026
CONCERTS
Strawberry Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
23 May 2026
FESTIVALS
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
NAACP Winchester Area Juneteenth 2026
Museum of the Shenandoah Valley
14 Jun 2026
JUNETEENTH
Hop Blossom Craft Beer Festival 2026
Old Town Winchester
6 Jun 2026
BEER-FESTIVALS
USD 7 TO 39
Pack 46 Grand Feature Parade Seats
Winchester
2 May 2026
FESTIVALS
USD 14
Apple Harvest Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
3 Oct 2026
FESTIVALS
66th Annual Apple Blossom Antique Car Meet
Jim Barnett Park
9 May 2026
CAR-SHOWS
Homestead Harvest Festival
2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603
24 Oct 2026
FESTIVALS
Live Dead & Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers
Bright Box Theater
3 May 2026
MUSIC
Peaches & Beaches Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
1 Aug 2026
FESTIVALS
Apple Harvest Festival
3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602
10 Oct 2026
FESTIVALS
Kids Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
27 Jun 2026
FESTIVALS
Bloomin' Brews & Boogie
145 N Loudoun St, Winchester, VA 22601-4717, United States
2 May 2026
MUSIC
Honeycrisp Festival
3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602
5 Sep 2026
FESTIVALS
Taste of Community Food Truck Festival
1460 University Dr, Winchester, VA 22601, United States
16 May 2026
FOOD-DRINKS
VA250 Fireworks Celebration
4063 Middle Rd, Winchester, VA, United States, Virginia 22602
11 Jul 2026
FIREWORKS
Patriotic Festival
3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602
11 Jul 2026
FESTIVALS
Pickle-chester
4305 Middle Road, Winchester, VA, United States, Virginia 22602
29 Aug 2026
FESTIVALS
Winchester Police Dept. 5th Annual Auto Show
100 W Piccadilly St, Winchester, VA 22601-3916, United States
23 May 2026
CAR-SHOWS
Pumpkin Festival
3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602
24 Oct 2026
FESTIVALS
Flutterby Fairy Festival 2026
740 Merrimans Ln Winchester, VA
6 Jun 2026
FESTIVALS
Beltane Luna Market 2026
125 S. Loudoun Street, Winchester, VA
9 May 2026
FESTIVALS
2026 Winchester Greek Festival
1700 Amherst St, Winchester, VA, United States, Virginia 22601
22 Aug 2026
FESTIVALS
The All Access Dance Party | Apple Blossom Festival Weekend
Backseat Events USA
1 May 2026
FESTIVALS
USD 18 TO 77
Fall Harvest Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
17 Oct 2026
FESTIVALS
2026 Shenandoah Apple Blossom Grand Feature Parade
Shenandoah Apple Blossom Festival®
2 May 2026
PARADES
Beltane Magic Market
105 Millwood Ave, Winchester, VA, United States, Virginia 22601
3 May 2026
Winchester Elks Lodge - Mack Berry Band (members & guest)
Elks Club
2 May 2026
MUSIC
Guest Reading: Kindred Roots Tarot
125 S. Loudoun Street, Winchester, VA
8 May 2026
FESTIVALS
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Winchester Festivals Events