Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Celtic Fest

 Sat, 14 Mar at 12:00 pm Old Town Winchester

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 pm James R. Wilkins, Jr. Athletic & Events Center

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 pm James R. Wilkins, Jr. Athletic & Events Center

Strawberry Festival

Sat, 23 May at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Country Nite @ Bright Box Theater in Winchester, VA

 Fri, 06 Mar at 07:00 pm Bright Box Theater USD 18 to 82

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

 Sat, 28 Feb at 08:00 pm Winchester Brew Works USD 18 to 79

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

First Friday

 Fri, 07 Aug at 05:00 pm Old Town Winchester Walking Mall

Peaches & Beaches Festival

Sat, 01 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

An Evening with Stephane Wrembel

 Fri, 27 Feb at 08:00 pm Bright Box (Winchester, VA)

New Playground Grand Opening Event

 Sat, 18 Apr at 11:00 am Winchester VA Parks and Recreation

90s & 00s Night @ Backseat Bar & Grill

 Sat, 18 Apr at 08:30 pm Backseat Bar and Grill

Jackyl — Chainsaws, Southern Rock and Loud Guitars

 Thu, 09 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

First Friday

 Fri, 05 Jun at 05:00 pm Old Town Winchester

Backseat Rocks with That Arena Rock Show

 Sat, 11 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

First Friday

 Fri, 03 Jul at 05:00 pm Old Town Winchester

Navy Federal Credit Union Veterans Dinner Show

 Wed, 29 Apr at 06:00 pm James R. Wilkins, Jr. Athletic & Events Center

Cash Party

 Sat, 21 Mar at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Willie Watson

 Fri, 10 Apr at 07:00 pm Bright Box Theater - VA

The All Access Dance Party | Apple Blossom Festival Weekend

 Fri, 01 May at 07:00 pm Backseat Events USA USD 18 to 77

Malloy Toyota Country Music Party

 Sat, 02 May at 08:00 pm James R. Wilkins, Jr. Athletic & Events Center

Comedy Night at James Charles Winery

 Sat, 21 Mar at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Micro Wrestling: Winchester, VA!

 Fri, 15 May at 08:00 pm Backseat Events

Harry Potter and the Goblet of Fire Movie Trivia

 Wed, 11 Mar at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Paella Day

 Sat, 28 Feb at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

5AM Trio: Esoterra Tour

 Thu, 26 Mar at 08:00 pm Bright Box Theater

Trivia Night

 Fri, 27 Mar at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Willows At Meadow Branch Young at Heart Dance

 Thu, 30 Apr at 11:00 am Millwood Station Banquet Hall

Our Town

 Thu, 26 Mar at 07:30 pm Glaize Studio Theatre

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

 Thu, 30 Apr at 08:00 pm Shenandoah Apple Blossom Festival®

90's Nickelodeon Trivia @ DCBC!

 Wed, 08 Apr at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

30 Years of The Reagan Years!

 Fri, 08 May at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Pajama Party | Ladies Night Out

 Sat, 09 May at 06:00 pm The George Washington A Wyndham Grand Hotel USD 89 to 120

Greener Living Day

 Sat, 25 Apr at 10:00 am 302 S Loudoun Street, Winchester, VA

Harlem Globetrotters 2026 - 100 Year Tour - Winchester, VA

 Wed, 04 Mar at 07:00 pm James R. Wilkins, Jr. Athletics & Events Center USD 32 to 309

The Lucky Brew Works Drag Show!

Sat, 07 Mar at 08:00 pm 320 N Cameron St, Winchester, VA

Live Dead & Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers

 Sun, 03 May at 07:00 pm Bright Box Theater

Country Music Party

 Fri, 01 May at 07:00 pm James R. Wilkins Jr. Athletics and Event Center

Trivia @ DCBC: I <3 the 90's!

Wed, 25 Feb at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

10th Annual Nitro Spring Fling

Sat, 21 Mar at 09:00 am 246 Sulky Dr., Winchester, VA, United States, Virginia 22602

Winchester Swing Dance Lesson & Social Dancing

 Thu, 26 Feb at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Queen's Ball and Dance Party

 Fri, 01 May at 08:30 pm 1300 Senseny Rd, Winchester, VA 22602-6418, United States

"Best In Show" Memorial Benefit Screening

 Sun, 01 Mar at 10:30 am 111 Featherbed Lane, Winchester, VA, United States, Virginia 22601

An Evening with Karen Jonas & Bobby Thompson

 Thu, 12 Mar at 07:30 pm Bright Box Theater

The Lion King (1994) Trivia

 Wed, 25 Mar at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Afro-Latin Social Dance Workshop

 Mon, 16 Mar at 07:00 pm Hazel-Pruitt Armory, Collaboratory 608 Millwood Ave Winchester, VA

WBW’s 10th Anniversary Party!!

 Sat, 16 May at 02:00 pm 320 N Cameron St, Winchester, VA

Wind Ensemble

 Thu, 05 Mar at 07:30 pm Armstrong Concert Hall

Contemporary Christian Concert presented by Clean Water of Virginia

 Sun, 03 May at 02:00 pm James R. Wilkins, Jr. Athletic & Events Center

Concern Hotline presents: A Taste of Winchester

 Thu, 09 Apr at 05:30 pm Fox Meadow Barn

The Crown College Choir Live at Lighthouse Baptist Church

 Wed, 25 Mar at 06:30 pm 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603

Little Noon Music with The Jon Rose Trio - Presented by Friends of HRLS

 Fri, 10 Apr at 12:00 pm 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Classical at the MSV: Fauré & Brahms

 Sat, 04 Apr at 02:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Alamo Winchester Film Club, Comic Book Couples Counseling & Four Color Fantasies present THE PHANTOM

 Sun, 15 Mar at 05:00 pm Alamo Drafthouse Winchester (Winchester, VA)

Katie's Backseat Bloom'n Dance Party

 Thu, 30 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

 Fri, 14 Nov at 08:00 pm Escutcheon Brewing Co. USD 13

Symphonic Band

 Tue, 03 Mar at 07:30 pm Armstrong Concert Hall

Cash Party Planning Meeting

Wed, 11 Mar at 06:00 pm Poblanos Mexican Grill

2026 Spring Third Winchester Battlefield 5k/10k/Half

 Sat, 25 Apr at 08:00 am 251 First Woods Dr, Winchester, VA 22603-5800, United States

Ballerina Nail & Spa Pumps and Pearls Ladies Party

 Mon, 27 Apr at 06:30 pm Bright Box (Winchester, VA)

Blue Fox Billiards, Bar and Grill

 Sat, 28 Feb at 09:00 pm Blue Fox Billiards, Bar and Grill

Cash Party Planning Meeting

Wed, 04 Mar at 06:00 pm Poblanos Mexican Grill

Dirty Dancing Trivia

 Wed, 08 Apr at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Valley Pediatric Dentistry Family Fun Party

 Tue, 28 Apr at 05:00 pm James R. Wilkins, Jr. Athletic & Events Center

Cash Party

 Sat, 14 Mar at 05:00 pm Winchester Moose Lodge 1283

Graham Barham in Winchester

 Sat, 02 May at 05:00 pm James R. Wilkins

Extreme unity presents an evening with Reclaim the Day.

Sat, 28 Feb at 05:00 pm What's New Worship

Blizzard Ball presented by NSV Civitan

 Fri, 27 Feb at 06:00 pm Calvary Baptist Church Free

Friday Night Fever Disco Dance Party

 Thu, 30 Apr at 07:00 pm James R. Wilkins Jr. Athletics and Event Center

The Eagles Club 824 presents Odie and The Country Band (members and invited guests only)

 Fri, 03 Jul at 07:00 pm Winchester Virginia Eagles Club 824

Music Jam on the Farm, Phelpsmore Lane

 Fri, 01 May at 06:00 pm 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

Open Music Jam on the Farm, Phelpsmore Lane

 Fri, 07 Aug at 06:00 pm 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

Tuba-Euphonium Studio

 Tue, 24 Mar at 07:30 pm Goodson Chapel Recital Hall

Winchester Elks Lodge

 Sat, 22 Aug at 07:00 pm Fraternal Order of Elks Lodge 867

The Reagan Years

 Thu, 07 May at 07:00 pm Backseat Events

Cash Party Planning Meeting

Wed, 25 Feb at 06:00 pm Poblanos Mexican Grill