Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Hang 10 Car & Dog Wash Firefighters' Parade

 Fri, 01 May at 06:00 pm Old Town, Winchester

GloFiber Grand Feature Parade

 Sat, 02 May at 01:30 pm Old Town, Winchester

Malloy Toyota Country Music Party

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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Contemporary Christian Concert presented by Clean Water of Virginia

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

Valley Pediatric Dentistry Family Fun Party

 Tue, 28 Apr at 05:00 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

Carter Myers Automotive Jimmy Buffett Tribute Show

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

Coronation of Queen Shenandoah

 Fri, 01 May at 01:30 pm John Handley High School

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

First Bank Men's Commonwealth Luncheon

 Fri, 01 May at 11:00 am Piccadilly's Public House and Restaurant

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

First Friday

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

The Travelin McCourys at Backseat Events

 Fri, 27 Mar at 08:00 pm Backseat Events

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

Peaches & Beaches Festival

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

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

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

Graham Barham in Winchester

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

New Playground Grand Opening Event

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

Navy Federal Credit Union Veterans Dinner Show

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

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

Cash Party

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

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

Glow in the Dark Easter Egg Hunt (Adults Only)

 Fri, 03 Apr at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Empanadas & Wine Pairing

 Sat, 25 Apr at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Ballerina Nail & Spa Pumps and Pearls Ladies Party

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

First Friday

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

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Queen's Ball and Dance Party

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

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Corks & Cakes

 Sat, 20 Jun at 01:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

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

The All Access Dance Party | Apple Blossom Festival Weekend

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

Willie Watson

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

The Amish Outlaws at Backseat Events

 Sat, 02 May at 08:00 pm Backseat Events

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

10th Annual Nitro Spring Fling

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

30 Years of The Reagan Years!

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

Trivia Night

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

90's Nickelodeon Trivia @ DCBC!

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

5AM Trio: Esoterra Tour

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

Willows At Meadow Branch Young at Heart Dance

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

Greener Living Day

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

Our Town

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

Pajama Party | Ladies Night Out

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

Drag bingo at 5050 taphouse

Fri, 20 Mar at 10:00 pm 5050Taphouse

Friday Night Fever Disco Dance Party

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

Country Music Party

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

The Lion King (1994) Trivia

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

JILL FULTON BAND @ PICCADILLY'S

 Sat, 09 May at 07:30 pm Piccadilly's Public House and Restaurant

Concern Hotline presents: A Taste of Winchester

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

Symphony Orchestra

 Thu, 02 Apr at 07:30 pm 1460 University Dr, Winchester, VA, United States, Virginia 22601

Dirty Dancing Trivia

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

WBW’s 10th Anniversary Party!!

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

Classical at the MSV: Fauré & Brahms

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

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

Balance Campaign

 Wed, 18 Mar at 08:00 pm Bright Box Theater

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

The Reagan Years

 Thu, 07 May at 07:00 pm Backseat Events

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

Winchester Elks - Tuff Luck Band

Sat, 25 Apr at 07:00 pm Fraternal Order of Elks Lodge 867

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

Winchester Elks Lodge - Mack Berry (members & signed in guest)

 Thu, 19 Mar at 06:00 pm The Elks Lodge Winchester

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

Combs Apple Blossom Party!

 Fri, 01 May at 12:00 pm Combs Wastewater Management