Winchester Festivals Events
Festivals Happening Next in Winchester, VA
United Bank Bloomin' Wine Fest
Downtown Walking Mall
24 Apr 2026
FESTIVALS
United Bank Bloomin' Wine Fest
Downtown Walking Mall
25 Apr 2026
FESTIVALS
Malloy Toyota Country Music Party
James R. Wilkins, Jr. Athletic & Events Center
2 May 2026
COUNTRY-MUSIC-FESTIVALS
Claudio’s Pizzeria Friday Night Fever Disco Dance Party
James R. Wilkins, Jr. Athletic & Events Center
1 May 2026
ENTERTAINMENT
Trex Music Fest
John Handley High School
1 May 2026
FIREWORKS
Valley Health 10K Race
John Handley High School
2 May 2026
SPORTS
Contemporary Christian Concert presented by Clean Water of Virginia
James R. Wilkins, Jr. Athletic & Events Center
3 May 2026
CONCERTS
Valley Pediatric Dentistry Family Fun Party
James R. Wilkins, Jr. Athletic & Events Center
28 Apr 2026
ART
Strawberry Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
23 May 2026
FESTIVALS
Carter Myers Automotive Jimmy Buffett Tribute Show
James R. Wilkins, Jr. Athletic & Events Center
30 Apr 2026
MUSIC
Coronation of Queen Shenandoah
John Handley High School
1 May 2026
CORONATION-WEEKEND
Sunflower Festival
2502 N. Frederick Pike, Winchester, VA
12 Sep 2026
FESTIVALS
Hop Blossom Craft Beer Festival 2026
Old Town Winchester
6 Jun 2026
BEER-FESTIVALS
USD 7 TO 39
A1A - Shenandoah Apple Blossom Festival - Winchester, VA
Shenandoah Apple Blossom Festival®
30 Apr 2026
FESTIVALS
NAACP Winchester Area Juneteenth 2026
Museum of the Shenandoah Valley
14 Jun 2026
MUSIC
Peaches & Beaches Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
1 Aug 2026
FESTIVALS
Live Dead & Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers
Bright Box Theater
3 May 2026
MUSIC
66th Annual Apple Blossom Antique Car Meet
Jim Barnett Park
9 May 2026
CAR-SHOWS
McDonald's Apple Blossom Gaming Festival
608 Millwood Ave, Winchester, VA 22601-5167, United States
25 Apr 2026
CONTESTS
WVU Medicine Pickleball Tournament
1300 Senseny Rd, Winchester, VA 22602-6418, United States
24 Apr 2026
SPORTS
Kids Festival
4305 Middle Road, Winchester, VA, United States, Virginia 22602
27 Jun 2026
FESTIVALS
Cash Party
250 Costello Dr, Winchester, VA 22602-4310, United States
21 Mar 2026
PARTIES
The YDC Spring Spectacular
302 S Loudoun Street, Winchester, VA
21 Mar 2026
KIDS
Pickle-chester
4305 Middle Road, Winchester, VA, United States, Virginia 22602
29 Aug 2026
FESTIVALS
Fiesta Latina
Winchester Sportsplex
26 Apr 2026
FESTIVALS
Queen's Ball and Dance Party
1300 Senseny Rd, Winchester, VA 22602-6418, United States
1 May 2026
PARTIES
VA250 Fireworks Celebration
4063 Middle Rd, Winchester, VA, United States, Virginia 22602
11 Jul 2026
Beltane Luna Market 2026
125 S. Loudoun Street, Winchester, VA
9 May 2026
FESTIVALS
West Oaks Farm Market's 2026 Spring Vendor Fair
West Oaks Farm Market
4 Apr 2026
HEALTH-WELLNESS
Winchester Police Dept. 5th Annual Auto Show
100 W Piccadilly St, Winchester, VA 22601-3916, United States
23 May 2026
CAR-SHOWS
Flutterby Fairy Festival 2026
740 Merrimans Ln Winchester, VA
6 Jun 2026
FESTIVALS
The All Access Dance Party | Apple Blossom Festival Weekend
Backseat Events USA
1 May 2026
FESTIVALS
USD 18 TO 77
10th Annual Nitro Spring Fling
246 Sulky Dr., Winchester, VA, United States, Virginia 22602
21 Mar 2026
SPRING-BREAK
Trex Fire Truck Rodeo, Antique Show & Kids' Activities
Millwood Station Banquet Hall
1 May 2026
KIDS
Apple Pie Baking Contest
Marker-Miller Orchards Farm Market
30 Apr 2026
CONTESTS
Claudio's Pizzeria The Bloom Store
Apple Blossom Mall
3 Apr 2026
FESTIVALS
Record Store Day 2026 at Back to the Media
48 South Loudoun St., Winchester, VA, United States, Virginia 22601
18 Apr 2026
TAYLOR-SWIFT
Symphony Orchestra
1460 University Dr, Winchester, VA, United States, Virginia 22601
2 Apr 2026
MUSIC
Beltane Magic Market
105 Millwood Ave, Winchester, VA, United States, Virginia 22601
3 May 2026
Bloomin' Wine Fest
Backseat Events
23 Apr 2026
FESTIVALS
Lunch & Learn: About Blooming Time
901 Amherst St, Winchester, VA, United States, Virginia 22601
7 Apr 2026
FESTIVALS
Apple Blossom Wine Festival
Taylor Pavillion Winchester Va
25 Apr 2026
FESTIVALS
Guest Reading: Kindred Roots Tarot
125 S. Loudoun Street, Winchester, VA
4 Apr 2026
FESTIVALS
World Tai Chi & Qigong Day
740 Merriman's Ln Winchester VA 22601
25 Apr 2026
HEALTH-WELLNESS
Guest Reading: Kindred Roots Tarot
125 S. Loudoun Street, Winchester, VA
18 Apr 2026
FESTIVALS
Teen Art Club: Apple Blossom
901 Amherst St, Winchester, VA, United States, Virginia 22601
9 Apr 2026
ART
Guest Reading: Kindred Roots Tarot
125 S. Loudoun Street, Winchester, VA
3 Apr 2026
FESTIVALS
Guest Reading: Kindred Roots Tarot
125 S. Loudoun Street, Winchester, VA
8 May 2026
FESTIVALS
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Winchester Festivals Events