Upcoming Festivals Events

Celtic Fest

 Old Town Winchester 14 Mar 2026
FESTIVALS

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

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Upcoming Food & Drinks Events

Peaches & Beaches Festival

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

Glazed and Confused

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 14 Mar 2026
WORKSHOPS

Cash Party

 250 Costello Dr, Winchester, VA 22602-4310, United States 21 Mar 2026
PARTIES

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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

Get Your Dreams On — Tell Me Lies: The Fleetwood Mac Experience

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 6 Feb 2026
MUSIC

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Upcoming Valentine's Day Events

Valentine's Day Dinner

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 14 Feb 2026
VALENTINES-DAY

Find your FURever Valentine Adoption Event

 111 Featherbed Lane, Winchester, VA, United States, Virginia 22601 14 Feb 2026
VALENTINES-DAY

Love Letters Evening

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 14 Feb 2026
ART

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Upcoming Comedy Events

Couples Therapy: A Comedy Show hosted by Rahmein Mostafavi

 Bright Box Theater 13 Feb 2026
COMEDY

Vibrissa's Got Talent!

Vibrissa Beer (Winchester, VA) 7 Feb 2026
PERFORMANCES

The Comedy Combo! A Free Standup Comedy Show at The Backseat Bar & Grill

 Backseat Bar and Grill 3 Feb 2026
COMEDY FREE

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Upcoming Galentines Day Events

Galentine's Night Out: Paint & Sip!

 302 S Loudoun Street, Winchester, VA 12 Feb 2026
GALENTINES-DAY

Galentines Paint & Sip!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 13 Feb 2026
GALENTINES-DAY

Valentine’s & Galentine’s Brunch at Patti’s Place

 Patti's Place 14 Feb 2026
BRUNCH USD 75

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Trending Events in Winchester

Thrift on Tap at DCBC: A Chocolate Escape Sip & Shop

 160 N Loudoun St, Winchester, VA, United States, Virginia 22601 7 Feb 2026
POP-UPS

Bakers & Artisans Handmade Indoor Pop Up

42 E. Piccadilly Street, Winchester, VA 6 Feb 2026
POP-UPS

Black History: Then and Now

 Handley Regional Library System 21 Feb 2026
BLACK-HISTORY-MONTH

Black History: Then and Now - Presented by Coming to the Table at Handley Library

 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 21 Feb 2026
BLACK-HISTORY-MONTH

The YDC Spring Spectacular

302 S Loudoun Street, Winchester, VA 21 Mar 2026
KIDS

Anthony's Pizza Spirit Night - Sr. Parent Committee Fundraiser

 Anthony's Pizza 19 Feb 2026
NONPROFIT

Big Game Watch Party at Rutter's 1747 Bar & Lounge

 1510 Coverstone Dr, Winchester, VA 22602, United States 8 Feb 2026
PARTIES

FREE COMMUNITY DANCE NIGHT

 Vibrissa Beer 19 Feb 2026
FREE

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

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

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

 Winchester Brew Works 28 Feb 2026
ENTERTAINMENT USD 18 TO 79

Someone Special Dance | presented by Finch Oral & Facial Surgery

 West Oaks Farm Market 7 Feb 2026

Spring Bridal Expo 2026

 The George Washington Hotel 1 Mar 2026
BUSINESS

66th Annual Apple Blossom Antique Car Meet

 Jim Barnett Park 9 May 2026
CAR-SHOWS

90s & 00s Night @ Backseat Bar & Grill

 Backseat Bar and Grill 18 Apr 2026
MUSIC

Kids Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 27 Jun 2026
FESTIVALS

More things to do in Winchester

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