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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Malloy Toyota Country Music Party

 Sat, 02 May at 08:00 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

Coronation of Queen Shenandoah

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

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 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

First Bank Men's Commonwealth Luncheon

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

Peach Festival

 Sat, 08 Aug at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Contemporary Christian Concert presented by Clean Water of Virginia

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

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

Sunflower Festival

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

NAACP Winchester Area Juneteenth 2026

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

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

First Friday

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

Apple Harvest Festival

Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

New Playground Grand Opening Event

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

Jackyl — Chainsaws, Southern Rock and Loud Guitars

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

Peaches & Beaches Festival

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

Graham Barham in Winchester

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

90s & 00s Night @ Backseat Bar & Grill

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

Navy Federal Credit Union Veterans Dinner Show

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

West Oaks Bloomin' Brunch and Bubbly 2026

 Sun, 26 Apr at 10:30 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

Backseat Rocks with That Arena Rock Show

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

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Ballerina Nail & Spa Pumps and Pearls Ladies Party

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

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

First Friday

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

90s Throwback Party ft. Dj OPHIE

 Sat, 18 Apr at 09:00 pm Bright Box Theater

Queen's Ball and Dance Party

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

Patriotic Festival

 Sat, 11 Jul at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 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

Micro Wrestling: Winchester, VA!

 Fri, 15 May at 08:00 pm Backseat Events

80s Prom Rescue Fundraiser

 Sat, 30 May at 07:00 pm Backseat Events

Corks & Cakes

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

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

Willows At Meadow Branch Young at Heart Dance

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

30 Years of The Reagan Years!

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

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

The Amish Outlaws at Backseat Events

 Sat, 02 May at 08:00 pm Backseat Events

Greener Living Day

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

90's Nickelodeon Trivia @ DCBC!

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

Pajama Party | Ladies Night Out

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

Country Music Party

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

Friday Night Fever Disco Dance Party

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

Dirty Dancing Trivia

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

Winchester Swing Dance - Spring Swing!

 Thu, 23 Apr at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Concern Hotline presents: A Taste of Winchester

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

JILL FULTON BAND @ PICCADILLY'S

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

Apple Blossom Welcome Board Paint & Sip

 Fri, 24 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

Katie's Backseat Bloom'n Dance Party

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

Winchester Elks Lodge - Mack Berry Band (members & guest)

 Sat, 02 May at 07:00 pm Elks Club

Gunshine Live: No Limits, Just Rock

 Fri, 24 Apr at 08:00 pm 114 Full House Drive , 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

Bluegrass on the Farm

 Thu, 11 Jun at 06:00 pm 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

The Reagan Years

 Thu, 07 May at 07:00 pm Backseat Events

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

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

The French-American Connection

 Sun, 19 Apr at 03:00 pm First Baptist Church Of Winchester

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

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

Winchester Elks Lodge

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

Winchester Elks

 Sat, 16 May at 07:00 pm Fraternal Order of Elks Lodge 867

Combs Apple Blossom Party!

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