Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

The Ghost of Christmas Past (A Paranormal Investigation)

 Sat, 13 Dec at 05:30 pm 101 N Loudoun St, Winchester, VA

"Clue Christmas" - A Murder Mystery Comedy Show // 7PM SHOW

 Sat, 13 Dec at 07:00 pm Bright Box Theater

Swing into the Holidays with Winchester Swing Dance

 Thu, 11 Dec at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Winchester Moose NYE Celebration - Tuff Luck Band

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

Winchester Elks Lodge - Mack Berry Band

 Sat, 24 Jan at 07:00 pm Elks Club

Big Hair, Bright Lights & Spank the 80s!

 Fri, 19 Dec at 08:00 pm 114 Full House Drive, Winchester, VA

Cow & Claus Ugly Sweater Party at Chick-fil-A

 Thu, 11 Dec at 05:00 pm 2230 S Pleasant Valley Rd, 22601

A DIVA's Christmas Special

 Sat, 20 Dec at 05:30 pm Bright Box (Winchester, VA)

Light the World

 Fri, 12 Dec at 06:00 pm 399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603

A Christmas Carol

 Sun, 14 Dec at 03:00 pm Grace Evangelical Lutheran Church 26 W Boscawen St A-201, Winchester, VA 22601

Dirty Santa Christmas Party!

 Sat, 20 Dec at 07:00 pm Broken Window Brewing Co.

Fork In The Road @ Winchester Eagles!

 Sat, 13 Dec at 07:00 pm Winchester Virginia Eagles Club 824

Collin Raye in Winchester

 Sat, 17 Jan at 08:00 pm Backseat Events

Flute Ensemble

 Sat, 13 Dec at 07:30 pm Goodson Chapel Recital Hall

FLW LIVE at Piccadillys!

 Fri, 19 Dec at 07:30 pm Piccadilly's Public House and Restaurant

Winchester Elks Lodge - Tuff Luck Band

Sat, 27 Dec at 07:00 pm Fraternal Order of Elks Lodge 867

Cash Party

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

Winter Disco Drag Show

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

Joe Nichols

 Wed, 28 Jan at 07:00 pm Backseat Events

Literacy Family Holiday Party with Santa

 Sat, 13 Dec at 02:00 pm Winchester Public Schools

Jackyl in Winchester

 Fri, 30 Jan at 08:00 pm Backseat Events

The Red Gobbo Secret Gift Exchange

 Sat, 13 Dec at 11:00 am 255 Market Street, Winchester, VA, United States, Virginia 22603

NW Works Chimers

 Sat, 13 Dec at 02:30 pm Armstrong Concert Hall

Old Town Winchester New Year's Eve Celebration 2026

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

Legacy Christian Academy Christmas Concert

 Tue, 16 Dec at 06:30 pm Daniel Morgan Middle School Free

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

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

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

Backseat Events - Joe Nichols - Mack Berry Band

 Thu, 29 Jan at 08:00 pm Backseat Events

14th Annual Beer & Carols Celebration

 Sun, 21 Dec at 06:00 pm Piccadilly's Public House and Restaurant

NW Works Chimers Concert

 Sat, 13 Dec at 02:30 pm Armstrong Concert Hall

Harry Potter Trivia @ DCBC!

 Wed, 17 Dec at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Kid’s Christmas Party!

 Sat, 13 Dec at 02:00 pm 1730 Berryville Pike

Holiday Concert: Yesterday Swing Orchestra

 Sun, 14 Dec at 01:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Cow & Claus Ugly Sweater Party

 Wed, 10 Dec at 05:00 pm 112 Market St, Winchester, VA 22603

Lebanese Wine Pairing Dinner at Byblos Winchester

 Sun, 25 Jan at 06:00 pm Byblos Winchester USD 77 to 87

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Van Buren Winds

 Sun, 14 Dec at 02:30 pm Armstrong Concert Hall

Backseat Event Center - Pre NYE Party

 Sat, 27 Dec at 02:00 pm 114 Full House Dr, Winchester, VA 22603-4645, United States

BRS Concert - The Very Best Time of Year...

 Sun, 14 Dec at 03:00 pm First Baptist Church Winchester, VA

Elf Movie trivia

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

Midnight in Miami: Bright Box NYE

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

Joe Nichols, Mack Berry Band in Winchester

 Thu, 29 Jan at 08:00 pm Backseat Events

Cash Party Planning Meeting

 Wed, 21 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

Winchester Elks Lodge

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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Cash Party Planning Meeting

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

Forrest Gump Trivia

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

Gift Wrapping Extravaganza

 Sun, 14 Dec at 12:00 pm ARE's RISE Center

Friday Night Fever Disco Dance Party

 Thu, 30 Apr James R. Wilkins Jr. Athletics and Event Center

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

Country Music Party

 Fri, 01 May James R. Wilkins Jr. Athletics and Event Center

Cash Party Planning Meeting

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

Ugly Sweater Party

Thu, 18 Dec at 08:00 pm Granny's Place

Cash Party Planning Meeting

 Mon, 15 Dec at 06:00 pm Poblanos Mexican Grill

Joey Harkum w/ The Grilled Lincolns

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

Briedé Family Vineyards - Mack Berry

 Fri, 26 Dec at 04:00 pm Briedé Family Vineyards

11 Principals that Separate Good Leaders from Exceptional CEO's

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

Winchester Audio Tour: Echoes of Legends and Landmarks

 Sat, 27 Sep at 12:00 pm Beth El Congregation (Winchester, Virginia) USD 6 to 40

NEW YEARS MASQUERADE PARTY

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

A Date Night Adventure! - Winchester Wonders

 Thu, 24 Jul at 08:00 am 12 N Cameron St USD 36

2025 Christmas Bake Sale and Take-Out

Sat, 20 Dec at 11:00 am 1700 Amherst St, Winchester, VA