Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Jackyl in Winchester

 Fri, 30 Jan at 08:00 pm Backseat Events

Joe Nichols, Mack Berry Band in Winchester

 Thu, 29 Jan at 08:00 pm Backseat Events

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

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

An Evening with Stephane Wrembel

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

Couples Therapy: A Comedy Show hosted by Rahmein Mostafavi

 Fri, 13 Feb at 08:00 pm Bright Box Theater

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

 Fri, 06 Feb at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Love Letters Evening

 Sat, 14 Feb at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Someone Special Dance | presented by Finch Oral & Facial Surgery

 Sat, 07 Feb at 06:00 pm West Oaks Farm Market

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Joe Nichols

 Wed, 28 Jan at 07:00 pm Backseat Events

For the Love of Linda: Honoring the Music of Linda Ronstadt

 Fri, 20 Feb at 08:00 pm Bright Box Theater

Cash Party

 Sat, 24 Jan at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

90s & 00s Night @ Backseat Bar & Grill

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

Winchester Swing Dance Lesson & Social Dancing

 Thu, 22 Jan at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Joey Harkum w/ The Grilled Lincolns

 Thu, 05 Feb at 07:00 pm Bright Box Theater

James & Joel: Great American Songwriters

 Sun, 22 Feb at 03:30 pm Bright Box Theater

Bridgerton

Fri, 30 Jan at 06:00 pm 157 N Loudoun St, Winchester, VA, United States, Virginia 22601

Sweethearts Swing Dance

 Thu, 12 Feb at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Jackyl — Chainsaws, Southern Rock and Loud Guitars

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

Houseplant Dishgarden Workshop

 Sat, 31 Jan at 02:00 pm 1912 Martinsburg Pike, Winchester, VA

Malevolent #1 World Premiere with Justin Jordan and Ben Templesmith!

 Wed, 28 Jan at 04:00 pm 80 Weems Ln, Winchester, VA, United States, Virginia 22601

Live Music with Brad the Guitar Guy

 Sat, 24 Jan at 02:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Spaghtti Dinner Buffet & Music from Allen Boyd & The Waysiders

 Fri, 23 Jan 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

Vibrissa's Got Talent!

Sat, 07 Feb at 08:00 pm Vibrissa Beer (Winchester, VA)

Comedy Night at James Charles Winery

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

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Malloy Toyota Country Music Party

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

90's Nickelodeon Trivia @ DCBC!

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

Perfect Pupusas!

 Sat, 24 Jan at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

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

Greener Living Day

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

Winchester Elks Lodge - Mack Berry Band

 Sat, 24 Jan at 07:00 pm Elks Club

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

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

Evans Home's Annual Chili Dinner

 Fri, 13 Feb at 05:00 pm Braddock Street United Methodist Church

The Lion King (1994) Trivia

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

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

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

5AM Trio: Esoterra Tour

 Thu, 26 Mar at 08:00 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

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

Anything But A Cup Party!

 Sat, 24 Jan 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

Galentine’s Night @K.Noel & Co.

 Thu, 05 Feb at 06:00 pm 161 Prosperity Dr Ste. 101, Winchester, VA

Contemporary Christian Concert presented by Clean Water of Virginia

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

Visual Bingo, Free Community event for everyone.

Thu, 22 Jan at 04:00 pm Chick-fil-A Pleasant Valley Road (2230 S Pleasant Valley Rd, )

Cash Party Planning Meeting

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

Cash Party

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

Forrest Gump Trivia

 Wed, 28 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Cash Party Planning Meeting

Wed, 11 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

WINTER BLUES??…JOIN US FOR A FUN EVENING WITH SPECIAL GUEST GUITARIST PAUL MAJETICH

Fri, 30 Jan at 07:00 pm Fraternal Order Of Eagles- Winchester

Navy Federal Credit Union Veterans Dinner Show

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

Ballerina Nail & Spa Pumps and Pearls Ladies Party

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

Graham Barham in Winchester

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

Winchester Elks Lodge

 Fri, 20 Feb at 07:00 pm Fraternal Order of Elks Lodge 867

Valley Pediatric Dentistry Family Fun Party

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

Friday Night Fever Disco Dance Party

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

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

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

Cash Party Planning Meeting

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

Cash Party Planning Meeting

 Wed, 21 Jan at 06:00 pm Poblanos Mexican Grill

Cash Party Planning Meeting

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