Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Colt Ford in Winchester

Fri, 16 May, 2025 at 08:00 pm Backseat Events

Creed Fisher in Winchester

Sat, 07 Jun, 2025 at 08:00 pm Backseat Events

Studio Big Band

Fri, 11 Apr, 2025 at 07:30 pm Armstrong Concert Hall

Malloy Toyota Country Music Party

Sat, 03 May, 2025 at 08:00 pm James R. Wilkins, Jr. Athletic & Events Center

Hayden Coffman at The Monument

Fri, 09 May, 2025 at 07:00 pm 186 North Loudoun Street, Winchester, VA

Trombone Collective

Tue, 22 Apr, 2025 at 07:30 pm Armstrong Concert Hall

Falstaff

Fri, 25 Apr, 2025 at 07:30 pm 1460 University Dr, Winchester, VA, United States, Virginia 22601

An Evening with Kate Baldwin

Tue, 29 Apr, 2025 at 07:30 pm Ohrstrom-Bryant Theatre

Hayden Coffman in Winchester

Fri, 09 May, 2025 at 07:00 pm The Monument

Essentially Ellington

Thu, 01 May, 2025 at 07:30 pm Ohrstrom-Bryant Theatre

Reggae Night @ Vibrissa Beer Winchester

Sat, 19 Apr, 2025 at 08:00 pm Vibrissa Beer (Winchester, VA)

ALL YOU NEED IS BEATLES: The Beatles Tribute

Sat, 07 Jun, 2025 at 08:00 pm Bright Box Theater USD 24 to 30

Chuggalug DUO at Piccadilly's (Winchester)!

Sat, 12 Apr, 2025 at 07:30 pm Piccadilly's Public House and Restaurant

HERE’S TO THE NIGHT is LIVE at The Monument!

Fri, 25 Apr, 2025 at 08:00 pm 186 North Loudoun Street, Winchester, VA

Hang 10 Car Wash Firefighters' Parade

Fri, 02 May, 2025 at 05:30 pm Old Town, Winchester

Rosie Soul Rocks the Night with special guests Rebel Soul!

Sat, 12 Apr, 2025 at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Apple Blossom Carnival

Fri, 25 Apr, 2025 at 05:00 pm Apple Blossom Mall

Reubens Health Pumps and Pearls Ladies Party

Mon, 28 Apr, 2025 at 06:30 pm The Monument VA

Silver Tones Swing Band: First Friday Winchester

Fri, 06 Jun, 2025 at 06:30 pm Taylor Pavillion Winchester Va

CONTEMPO Touring Ensemble: A Night of Iconic Hits

Sat, 12 Apr, 2025 at 07:30 pm 28 W Hart St USD 13

Glo Fiber Grand Feature Parade

Sat, 03 May, 2025 at 01:30 pm Old Town Winchester

Claudio's Pizzeria '80s Dance Party

Fri, 02 May, 2025 at 08:00 pm James R. Wilkins, Jr. Athletic & Events Center

An Evening with Buddy Holly featuring Robbie Limon

Fri, 18 Apr, 2025 at 07:30 pm Bright Box Theater USD 29 to 34

Winchester Meadow Celebration

Sat, 26 Apr, 2025 at 03:00 pm Jim Barnett Park

Uncruel Summer - A Girly Pop Dance Party

Thu, 01 May, 2025 at 07:00 pm Bright Box Theater - VA

Queen's Ball and Dance Party

Fri, 02 May, 2025 at 08:30 pm The George Washington Hotel

90s & 00s Night @ The Monument VA

Sat, 26 Apr, 2025 at 08:00 pm The Monument VA

🌸✨ The Blossom & Bloom Ladies Lunch & Dance Party ✨🌸

Fri, 02 May, 2025 at 10:00 am 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Carter Myers Automotive Ultimate DJ Party

Thu, 01 May, 2025 at 08:00 pm James R. Wilkins, Jr. Athletic & Events Center

Colt Ford Live: Country Rock Party Night

Fri, 16 May, 2025 at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

The Local Honeys

Sat, 14 Jun, 2025 at 07:00 pm Bright Box Theater USD 21 to 23

An Evening With the Kelly Bell Band

Fri, 13 Jun, 2025 at 08:00 pm Bright Box Theater USD 23 to 29

2000's Dance Party - Apple Blossom Edition

Sat, 03 May, 2025 at 09:00 pm Bright Box Theater USD 13 to 19

1st Annual Ambrogi Acres 420 Event at Backseat Event Center

Sat, 19 Apr, 2025 at 01:00 pm 114 Full House Dr, Winchester, VA 22603-4645, United States

It's A 70's Flashback - Disco Style

Wed, 30 Apr, 2025 at 07:00 pm Backseat Events

Anchored In Song - A Blue Ridge Singers Concert

Sun, 27 Apr, 2025 at 03:00 pm First Baptist Church

Trivia @ DCBC: 1 <3 the 90's!

Wed, 30 Apr, 2025 at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Southall – Live at The Monument for the 10th Anniversary of Six String Sorrow

Sat, 21 Jun, 2025 at 07:00 pm 186 North Loudoun Street, Winchester, VA

Breach the Silence w/ Saint Diablo and Devil in Disguise

Fri, 09 May, 2025 at 08:00 pm Bright Box Theater USD 13 to 19

First Bank Men's Commonwealth Luncheon

Fri, 02 May, 2025 at 11:00 am Piccadilly's Public House and Restaurant

WVU Medicine Pickleball Tournament

Sat, 26 Apr, 2025 at 09:00 am 1300 Senseny Rd, Winchester, VA 22602-6418, United States

The Flying Ivories: Dueling Pianos (7PM SHOW) - ALL AGES

Sat, 31 May, 2025 at 07:00 pm Bright Box Theater USD 22 to 27

WBW’s 9th Anniversary Party!!!

Sat, 17 May, 2025 at 12:00 pm 320 N Cameron St, Winchester, VA

Broken Hearts: Tribute to Tom Petty & The Heartbreakers

Sun, 22 Jun, 2025 at 07:00 pm Bright Box Theater USD 29 to 39

90's Rockfest: Stone Temple Pilots & Rage Against The Machine Tributes

Sat, 17 May, 2025 at 08:00 pm Bright Box Theater USD 24 to 30

Valley Pediatric Dentistry Family Fun Party

Tue, 29 Apr, 2025 at 05:00 pm James R. Wilkins, Jr. Athletic & Events Center

Ambrogi Acres 1st Annual 420 Event

Sat, 19 Apr, 2025 at 01:00 pm 114 Full House Dr USD 23 to 109

On the Boat at Piccadilly

Sat, 28 Jun, 2025 at 07:00 pm Piccadilly's Public House and Restaurant

Josh Allen Band at Winchester Eagles

Fri, 25 Apr, 2025 at 07:00 pm Winchester Virginia Eagles Club 824

Shenandoah Apple Blossom Wine Festival

Sat, 26 Apr, 2025 at 03:00 pm 9 court square, Winchester, VA 22601

Symphonic Band

Sun, 27 Apr, 2025 at 02:30 pm Armstrong Concert Hall

Buffalo Wabs & The Price Hill Hustle

Sat, 21 Jun, 2025 at 07:00 pm Bright Box Theater USD 18 to 21

MELISSA CARPER w/ special guest Todd Day Wait

Thu, 22 May, 2025 at 07:00 pm Bright Box Theater USD 22 to 28

Tyler Braden in Winchester

Sat, 14 Jun, 2025 at 07:00 pm The Monument

Car Show

Sun, 27 Apr, 2025 at 12:00 pm Millbrook High School

Coronation of Queen Shenandoah

Fri, 02 May, 2025 at 01:30 pm John Handley High School

Joey Harkum (Solo)

Thu, 31 Jul, 2025 at 07:00 pm Bright Box Theater USD 18 to 23

GROOVALICIOUS: A Night of Disco Entertainment

Thu, 01 May, 2025 at 06:00 pm Backseat Events

Honors Chamber Music Recital

Tue, 15 Apr, 2025 at 06:30 pm Goodson Chapel Recital Hall

Trainwreck LIVE at the United Bank Bloomin' Wine Fest!

Sat, 26 Apr, 2025 at 11:00 am Taylor Pavilion Winchester

Willows At Meadow Branch Young at Heart Dance

Thu, 01 May, 2025 at 11:00 am Millwood Station Banquet Hall

Winchester, VA - Midget Wrestling All * Stars @ The Monument

Wed, 11 Jun, 2025 at 08:00 pm The Monument VA

NW Works Chimers

Sat, 26 Apr, 2025 at 02:30 pm Armstrong Concert Hall

Van Buren Winds

Wed, 16 Apr, 2025 at 07:30 pm Armstrong Concert Hall

Adopt a Plush Pet Party

Thu, 17 Apr, 2025 at 03:00 pm 111 Featherbed Ln, Winchester, VA 22601-4486, United States

My Heart Wants to Sing (Winchester, VA)

Sat, 12 Jul, 2025 at 02:00 pm Handley Regional Library System

Winchester Elks Lodge

Fri, 13 Jun, 2025 at 07:00 pm 466 Front Royal Pike, Winchester, VA 22602-7315, United States

Clarinet Choir

Mon, 28 Apr, 2025 at 07:30 pm Armstrong Concert Hall

Winchester Moose - Tuff Luck Band

Fri, 27 Jun, 2025 at 07:00 pm Winchester Moose Family Center 1283

Winchester Elks Lodge

Fri, 19 Sep, 2025 at 07:00 pm 466 Front Royal Pike, Winchester, VA 22602-7315, United States

Hip Hop Showcase The Takeover Live Performance

Fri, 11 Apr, 2025 at 11:00 pm The Monument VA

Celebración of Winchester

Sat, 20 Sep, 2025 at 12:00 pm Old Town Winchester Walking Mall

Bloomin' with Backseat Hawaiian Luau!

Sat, 26 Apr, 2025 at 07:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

2025 Third Winchester Battlefield 5k/10k/Half

Sat, 09 Aug, 2025 at 07:30 am 251 First Woods Dr, Winchester, VA 22603-5800, United States

Rehab @ Backseat Events in Winchester

Wed, 28 May, 2025 at 03:00 pm Backseat Events