Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Old Town Winchester New Year's Eve Celebration 2026

 Wed, 31 Dec at 06:00 pm Old Town, Winchester

Winchester Moose NYE Celebration - Tuff Luck Band

Wed, 31 Dec at 06:00 pm Winchester Moose Lodge 1283

Live Music at Piccadilly's

 Fri, 02 Jan at 07:30 pm Piccadilly's Public House and Restaurant

Strawberry Festival

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

Perfect Pupusas!

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

Elf Movie trivia

 Wed, 14 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Winter Disco Drag Show

 Sat, 10 Jan at 08:00 pm Winchester Brew Works USD 18

Steak Dinner & Live Music from Those 3 Guys

 Fri, 16 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Cash Party

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

Winter Paint and Sip @ West Oaks with The Typewriter Studio

 Fri, 09 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Malloy Toyota Country Music Party

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

Winchester Elks Lodge - Mack Berry Band

 Sat, 24 Jan at 07:00 pm Elks Club

Winchester Elks Lodge

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

New Year's Eve Extravaganza

 Wed, 31 Dec at 09:00 pm 6 Richards Avenue, Winchester, VA, United States, Virginia 22601

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Midnight in Miami: Bright Box NYE

 Wed, 31 Dec at 09:00 pm Bright Box Theater

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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Noon Year's Eve

 Wed, 31 Dec at 11:00 am 157 N Loudoun St, Winchester, VA, United States, Virginia 22601

5AM Trio: Esoterra Tour

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

Cash Party Planning Meeting

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

New Year’s Eve with Rob Talton, Nick Nerangis and Friends!

Wed, 31 Dec at 10:00 pm 103 E Piccadilly St, Winchester, VA

ReadStart: January Spotlight Series

 Sat, 17 Jan at 10:00 am 302 S Loudoun Street, Winchester, VA

Joe Nichols, Mack Berry Band in Winchester

 Thu, 29 Jan at 08:00 pm Backseat Events

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

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

Joe Nichols

 Wed, 28 Jan at 07:00 pm Backseat Events

Jackyl in Winchester

 Fri, 30 Jan at 08:00 pm Backseat Events

Cash Party Planning Meeting

 Thu, 08 Jan at 06:00 pm Poblanos Mexican Grill

Carter Myers Automotive Jimmy Buffett Tribute Show

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

USRC Winter Championship Race

 Sat, 17 Jan at 08:00 am 246 Sulky Dr., Winchester, VA, United States, Virginia 22602

Forrest Gump Trivia

 Wed, 28 Jan at 06:00 pm 4305 Middle Road, 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)

Dirty Dancing Trivia

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

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

Cash Party

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

Cash Party Planning Meeting

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

Cash Party Planning Meeting

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

Cash Party Planning Meeting

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

Navy Federal Credit Union Veterans Dinner Show

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

Cash Party Planning Meeting

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

Country Music Party

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

Contemporary Christian Concert presented by Clean Water of Virginia

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

Graham Barham in Winchester

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

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

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

Joey Harkum w/ The Grilled Lincolns

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

11 Principals that Separate Good Leaders from Exceptional CEO's

 Fri, 09 Jan at 08:30 am Winchester Regional Airport (OKV) Free

NEW YEARS MASQUERADE PARTY

 Wed, 31 Dec at 08:00 pm Backseat Events USD 34