Upcoming Festivals Events

Celtic Fest

 Old Town Winchester 14 Mar 2026
FESTIVALS

Carter Myers Automotive Jimmy Buffett Tribute Show

 James R. Wilkins, Jr. Athletic & Events Center 30 Apr 2026
MUSIC

Strawberry Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 23 May 2026
FESTIVALS

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Upcoming Food & Drinks Events

West Oaks 7th Annual Adult Egg Hunt

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 29 Mar 2026
EASTER

Peaches & Beaches Festival

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

Hop Blossom Craft Beer Festival 2026

 Old Town Winchester 6 Jun 2026
BEER-FESTIVALS USD 7 TO 39

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Upcoming Live Music Events

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 James R. Wilkins, Jr. Athletic & Events Center 1 May 2026
ENTERTAINMENT

Country Nite @ Bright Box Theater in Winchester, VA

 Bright Box Theater 6 Mar 2026
MUSIC USD 18 TO 82

Jackyl in Winchester

 Backseat Events 9 Apr 2026
CONCERTS

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Upcoming Comedy Events

Catch Me If You Can

 Ohrstrom-Bryant Theatre 26 Feb 2026
ENTERTAINMENT

Comedy Night at James Charles Winery

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 21 Mar 2026
COMEDY

Napoleon Dynamite Trivia

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 25 Feb 2026
COMEDY

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Trending Events in Winchester

🍀🎻 Saint Patrick’s Party at West Oaks! 🎻🍀

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 13 Mar 2026

Flashlight Egg Hunt

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 20 Mar 2026
EASTER-EGG-HUNT

VA250 Fireworks Celebration

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 11 Jul 2026

Trex Music Fest

 John Handley High School 1 May 2026
FIREWORKS

Celebrating Black History Month: History & Cocktails Night

 Bright Box (Winchester, VA) 26 Feb 2026
BLACK-HISTORY-MONTH

Easter Breads

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 28 Mar 2026
EASTER

2026 Easter Bake Sale and Greek Take-Out

 1700 Amherst St, Winchester, VA 28 Mar 2026

HoneyWay Apple Blossom Golf Classic

 Rock Harbor Golf Course 24 Apr 2026
SPORTS

Coronation of Queen Shenandoah

 John Handley High School 1 May 2026
PERFORMANCES

First Bank Men's Commonwealth Luncheon

 Piccadilly's Public House and Restaurant 1 May 2026

Shades of HUNKS at Winchester Brew Works (Winchester, VA) 02/28/26

 Winchester Brew Works 28 Feb 2026
ENTERTAINMENT USD 18 TO 79

First Friday

 Old Town Winchester Walking Mall 7 Aug 2026
MUSIC

32nd Annual Valley Health Community Wellness Festival

 Apple Blossom Mall 28 Feb 2026
HEALTH-WELLNESS

West Oaks Spring Vendor Fair 2026

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 4 Apr 2026

Rhea Lana's of Winchester Spring/Summer Family Shopping Event!

 221 Commonwealth Ct, Winchester, VA 22602, USA 18 Mar 2026
SHOPPING

More things to do in Winchester

Festivals
Food & Drinks
Live Music
Comedy
Easter
Black History Month
Fireworks
Easter Egg Hunt
Valentine's Day
St. Patrick's Day
Mardi Gras
Galentines Day
Speed Dating
Carnivals
Music Festivals
Bar Crawls
Pop-Ups