Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Wings and Wheels - Winchester, VA

 Sat, 18 Oct at 10:00 am Winchester Regional Airport - OKV

West Oaks Apple Harvest Festival!

 Sun, 05 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Trunk or Treat on Loudoun Street!

 Sat, 18 Oct at 06:00 pm 302 S Loudoun Street, Winchester, VA

Pandora's Box - The Ultimate Tribute to Aerosmith & Special Guests AIRMONT ROAD - SAT OCT 11

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

Build Your Own CEMETARIUM!

 Fri, 10 Oct at 06:00 pm 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

80s Night with The Reagan Years

 Fri, 07 Nov at 07:00 pm 186 North Loudoun Street, Winchester, VA

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

 Sat, 04 Oct at 08:00 pm 114 Full House Drive, Winchester, VA

Backseat's Haunted Metal Bash

 Fri, 31 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

The Reflex - 80's Tribute Band & The Blue Genies

 Thu, 23 Oct at 07:00 pm Backseat Events

Micky & The Motorcars

 Sat, 04 Oct at 07:00 pm Bright Box Theater

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

Emo Night Karaoke 10/3 @ Bright Box Theater

 Fri, 03 Oct at 08:00 pm Bright Box Theater USD 21

Bag Bingo Fundraiser

 Sat, 11 Oct at 06:00 pm 425 Handley Blvd, 22601

Low Water Bridge Band & Jake Kohn – Co‑Headline Hometown Show

 Sat, 04 Oct at 08:00 pm Taylor Pavillion Winchester Va

HalloWinchester Pub Crawl

 Sat, 25 Oct at 06:00 pm 14 W Boscawen St USD 10

Saving Abel with Anger Box

 Thu, 16 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Aaron Tippin at Backseat Events

 Sat, 08 Nov at 08:00 pm Backseat Events

The SideMen

 Sat, 01 Nov at 07:00 pm Winchester Moose Lodge USD 34 to 500

Pride Kick Off!

 Fri, 03 Oct at 06:00 pm 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601

2025 Winchester Medical Center NICU Reunion

 Sun, 12 Oct at 01:00 pm West Oaks Farm Market

Karaoke Night with Route 11 DJ

 Fri, 24 Oct at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Katie's Halloween Cash Party

 Sat, 25 Oct at 05:30 pm Backseat Events USD 55

West Oaks Fall Harvest Festival!

 Sun, 19 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Anything But A Cup Party!

 Sat, 18 Oct at 02:00 pm 320 N Cameron St, Winchester, VA

Aaron Tippin - Stand for America at Backseat Events!

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

Brian Head Welch and Friends

 Sat, 08 Nov at 04:30 pm 2249 valor dr winchester va

Mountain Drive Band @ Winchester Eagles

 Fri, 03 Oct at 07:00 pm Winchester Virginia Eagles Club 824

Penntera, Monolith & Priest Unleashed - High Voltage ROCK Night

 Sat, 04 Oct at 08:00 pm Backseat Events

The Bass Club Presents: G-SPACE | SATURN RETURN TOUR

 Sat, 11 Oct at 09:00 pm Bright Box Theater

Texas Hippie Coalition

 Thu, 16 Oct at 07:00 pm Backseat Events

CASH PARTY

Sat, 04 Oct at 05:00 pm Winchester Moose Lodge.

West Oaks Farm Market - Mack Berry

 Sat, 04 Oct at 12:30 pm West Oaks Farm Market

Recruit Ready Basketball Showcase

 Sat, 11 Oct at 10:00 am 1001 War Memorial Dr, Winchester VA

5-Elemental Lotus Healing Class

 Sat, 25 Oct at 01:00 pm Lykens Chiropractic, Inc.

Texas Hippie Coalition & Friends

 Fri, 17 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Halloween Happenings

 Sat, 25 Oct at 06:00 pm 107 North Kent Street, Winchester, VA, United States, Virginia 22601

Pandora's Box - Aerosmith Tribute Band

 Fri, 10 Oct at 07:00 pm Backseat Events

Jake Kohn & Low Water Bridge Band

 Fri, 03 Oct at 07:00 pm The Monument - VA

Karaoke Night with Route 11 DJ

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

90s Night with Doc Martin and the Flannel

 Sat, 18 Oct at 07:00 pm 186 North Loudoun Street, Winchester, VA

Caleb Michael Gordon Group

 Sat, 18 Oct at 07:30 pm 28 W Hart St, Winchester, VA 22601-4513, United States

"It Don't Mean a Thing" Swing Dance with the Silver Tones Swing Band

 Sat, 01 Nov at 06:30 pm Brandt Student Center

Saving Abel

 Wed, 15 Oct at 07:00 pm Backseat Events

The Lowdown Drifters at The Monument

 Sun, 05 Oct at 07:00 pm The Monument

2025 Together Women's Conference

Fri, 10 Oct at 06:00 pm 2080 N Frederick Pike, 22603

WHLC CASH PARTY

 Sat, 04 Oct at 05:00 pm Winchester Moose Lodge.

Winchester Eagles with Guest Morgan Jenkins

Fri, 10 Oct at 07:00 pm 700 Baker Ln, Winchester, VA 22601-5679, United States

Winchester Swing Dance Lesson & Social Dancing

 Thu, 09 Oct at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Cash Party Planning Meeting

Wed, 15 Oct at 06:00 pm Poblanos Mexican Grill

Austin Meade + Elvie Shane Co-Headline

 Sat, 08 Nov at 07:00 pm 186 North Loudoun Street, Winchester, VA

C-Suite

 Fri, 07 Nov at 08:30 am 491 Airport Rd Free

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Día de Muertos

Sun, 02 Nov at 04:00 pm Braddock Street United Methodist Church

Winchester Moose Lodge

 Sat, 08 Nov at 07:00 pm 215 E Cork St, Winchester, VA 22601-5018, United States

Christmas Bake Sale and Take-Out

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

Halloween Party!!

 Sat, 18 Oct at 06:00 pm 164 Poorhouse Rd, Winchester, VA, United States, Virginia 22602

Chocolate Lovers

 Sat, 11 Oct at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Build Your Own CEMETARIUM!

 Sat, 25 Oct at 06:00 pm 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

Elijah - Artist

 Thu, 20 Nov at 07:00 pm The Monument - VA

Big Hair, Bright Lights & Spank the 80s! Dec 19 2025

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

A Christmas Carol at Winchester Little Theatre Inc.

 Fri, 07 Nov at 08:00 pm Winchester Little Theatre Inc.

Night Of Comedy at What's New Worship

 Sat, 04 Oct at 06:30 pm 2249 Valor Dr, Winchester, VA 22601-3698, United States

Winchester Eagles With Guest Morgan Jenkins

 Fri, 14 Nov at 07:00 pm 700 Baker Ln, Winchester, VA 22601-5679, United States

The Reagan Years returns to The Monument, Winchester VA

 Fri, 07 Nov at 08:00 pm The Monument VA

RVG:TZM [Slaughterbrew Farewell], AMETROPIA, and OPERATION: DEATH | 10/4 @ Blue Fox, Winchester, VA

 Sat, 04 Oct at 07:00 pm Blue Fox Billiards

Cash Party Planning

Mon, 17 Nov at 06:00 pm Poblanos Mexican Grill

Cash Party

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

Sauce It Up

 Sun, 12 Oct at 02:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Winchester Elks Lodge - Tuff Luck Band

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

The Stillwater Band @ Winchester, VA Eagles

 Sat, 06 Dec at 07:00 pm Winchester Virginia Eagles Club 824

Backseat Event Center - Pre NYE Party

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

Winchester Moose NYE Celebration - Tuff Luck Band

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

Trainwreck LIVE at WOFM Fall Festival

 Sat, 18 Oct at 04:00 am 4305 Middle Rd, Winchester, VA 22602, United States

HOLY COW WE’RE HAVING A BABY!!!

Sun, 02 Nov at 02:20 pm War Memorial Building, Jim Barnett Park

Holiday Concert: Yesterday Swing Orchestra

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

Robbie Limon Band Thanksgiving Eve Party

 Wed, 26 Nov at 07:00 pm Bright Box Theater

Little Noon Music - Shenandoah Conservatory's Trombone Collective

 Fri, 05 Dec at 12:00 pm 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Dill Pickers at West Oaks Farm Market October 11, 2025

 Sat, 11 Oct at 12:30 pm West Oaks Farm Market

Trainwreck LIVE at WOFM Fall Festival

 Sun, 19 Oct at 01:00 pm West Oaks Farm Market

Cash Party Planning

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

NEW YEARS MASQUERADE PARTY

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

Holiday Bluegrass Concert: Jack Dunlap

 Sun, 07 Dec at 01:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601