Entertainment Events in Winchester

Check out happening entertainment events all around Winchester, VA

4th Annual FREE Community Day & CRAFT SHOW

 Sat Jul 20 2024 at 09:00 am 1001 E Cork St, Winchester, VA 22601-5575, United States

Winchester Sports Card Pokémon & Collectibles Show June 29

 Sat Jun 29 2024 at 09:00 am Millwood Station Bingo Hall Free

Rockin' Independence Eve

 Wed Jul 03 2024 at 02:00 pm Old Town Winchester, VA

June Sunset Series

Thu Jun 27 2024 at 05:30 pm 19 W Cork St, Winchester, VA, United States, Virginia 22601

Winchester Children’s Business Fair

 Sat Jun 29 2024 at 11:00 am Winchester Moose Lodge.

DJ Night @ Backseat Events | Winchester VA

 Fri Jun 28 2024 at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Dino Delray LIVE!

 Fri Jul 05 2024 at 05:00 pm James Charles Winery & Vineyard

Styled SHOOTS – Virginia

 Tue Aug 13 2024 at 08:00 am The George Washington Hotel

Sunflower Festival 2024

 Sat Sep 14 2024 at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

Anthony Stoika Trio

 Fri Jun 28 2024 at 07:00 pm 11 W Oates Avenue , Winchester, VA, United States, Virginia 22601

Friday Night Party w/ DJ Ophie

 Fri Jul 12 2024 at 09:00 pm Bright Box Theater USD 0 to 10

Chris Rosenburg LIVE!

 Fri Aug 02 2024 at 05:00 pm James Charles Winery & Vineyard

Jesse Daniel w/ Two Runner Live @ The Monument

 Thu Sep 19 2024 at 07:00 pm 186 North Loudoun Street, Winchester, VA

HillBilly Casino w/ Sasquatch and The Sick-a-Billys

 Wed Jul 10 2024 at 08:00 pm Bright Box Theater USD 17 to 20

Murphy's Bluegrass Bandits at Hog-It-Up BBQ!

Sat Aug 10 2024 at 05:00 pm Hog-It-Up BBQ, Bar & Saloon

East Coast Vs. West Coast Hip-Hop Dance Night

 Sat Jul 20 2024 at 09:00 pm Bright Box Theater USD 10 to 15

The Diamond Ball: A Bridgerton Tea

 Fri Aug 02 2024 at 06:30 pm 217 W. Boscawen St., Winchester, VA, United States, Virginia

AGU at West Oaks Farm Market

Sat Jun 29 2024 at 12:00 pm West Oaks Farm Market

14th Annual Patsy Cline Block Party

 Sat Aug 31 2024 at 10:00 am 608 South Kent Street, Winchester, VA, United States, Virginia 22601

Movie Night @ The Rink

 Fri Jul 26 2024 at 07:00 pm James Wood Middle School

No Surprises: The DMV's Tribute to Radiohead w/ The Siamese Dreamers

 Sat Aug 03 2024 at 07:00 pm Bright Box Theater USD 15 to 20

August Pickup Party at Weaver Park

 Thu Aug 01 2024 at 05:30 pm 167 Bruce Dr., Winchester, VA 22061

Monoflo International Concert Series 2024 #2

 Sat Aug 24 2024 at 06:30 pm Bright Box Theater

Backseat Events - Winchester, VA

 Fri Aug 23 2024 at 08:00 pm Backseat Events

11th Annual AbNormal Formal

 Sat Sep 07 2024 at 07:45 pm Piccadilly's Public House and Restaurant

Neighborhood Nights - Whittier Park

 Thu Sep 12 2024 at 06:30 pm Whittier Park

September Pickup Party at Frederick Douglass Park

 Thu Sep 05 2024 at 05:30 pm 589 N Kent St, Winchester, VA 22601-5345, United States

PSYCHEDELIC ROCK NIGHT W/ STRANGE SOULS (THE DOORS) & GYPSY ROSE (HENDRIX)

 Sat Sep 07 2024 at 08:00 pm Bright Box Theater USD 18 to 22

Joe Stamm Band w/ TBD

 Thu Sep 26 2024 at 07:00 pm Bright Box Theater USD 15 to 18

Wright Live/ Blue Fox present: A Benefit For Jay Powell: feat. Raised On Analog, The Punky Brewsters

 Fri Jun 28 2024 at 07:00 pm Blue Fox Billiards, Bar and Grill

ShenArtsFest

 Sat Sep 07 2024 at 10:00 am Downtown Walking Mall

Winchester Elks

 Sat Aug 31 2024 at 07:00 pm Fraternal Order of Elks Lodge 867

Orpheum Arts Assembly: Arts and Entertainment Networking

 Sat Jun 29 2024 at 07:00 pm Drum Orpheum Rehearsal Hall, West Oates Avenue, Winchester, VA, USA Free

Winchester Elks Lodge

 Sat Jul 13 2024 at 07:00 pm Fraternal Order of Elks Lodge 867

Sunflower Festival 2024

 Sat Sep 14 2024 at 10:00 am The Homestead Farm at Fruit Hill Orchard USD 0 to 5

JILL FULTON BAND @ PICCADILLYS

 Fri Aug 23 2024 at 07:30 pm Piccadilly's Public House and Restaurant

Piccadilly's Public House & Restaurant

 Sat Sep 07 2024 at 07:30 pm 125 E Piccadilly St, Winchester, VA 22601-5004, United States

PURPLE RAIN Movie Party

 Sat Jul 13 2024 at 09:00 pm Alamo Drafthouse Winchester (Winchester, VA)

The Natioal Jazz Workshop

 Sun Jul 14 2024 at 02:00 pm Shenandoah Conservatory

Alamo Winchester Film Club #1154: Criterion Challenge #67: Cocteau's THE BLOOD OF A POET [1930]

 Wed Jul 10 2024 at 07:00 pm Alamo Drafthouse Winchester (Winchester, VA)

Katie's Fall Cash Party

 Sat Nov 09 2024 at 05:30 pm West Oaks Farm Market USD 50

Musician's Mastermind Challenge

 Wed Apr 24 2024 at 07:00 pm Drum Orpheum Rehearsal Hall, West Oates Avenue, Winchester, VA, USA Free

Winchester Moose

 Sat Aug 24 2024 at 07:00 pm 215 E Cork St, Winchester, VA 22601-5018, United States

Winchester Moose

 Sat Dec 07 2024 at 08:00 pm 215 E Cork St, Winchester, VA 22601-5018, United States

Winchester Elks Lodge

 Sat Nov 16 2024 at 08:00 pm Fraternal Order of Elks Lodge 867

An Evening with Black Flag

 Mon Aug 19 2024 at 07:30 pm Bright Box Theater USD 35 to 38

An Evening with Trish Toledo

 Fri Jun 28 2024 at 08:00 pm Bright Box Theater USD 25 to 30

Back Roads & Boot Scootin': 90's Country Night - 21+

 Sat Jun 29 2024 at 09:00 pm Bright Box Theater USD 10

Back Roads & Boot Scootin': 90s Country Night Ft. DJ Ophie

 Sat Jun 29 2024 at 09:00 pm Bright Box Theater

An Evening with Trish Toledo

 Fri Jun 28 2024 at 08:00 pm Bright Box Theater

July Pickup Party at Timbrook Park

 Thu Jul 11 2024 at 05:30 pm 210 E. Piccadilly Street, Winchester, VA 22601

The Flying Ivories: Dueling Pianos (9:30PM SHOW) - 18+

 Sat Jul 27 2024 at 09:30 pm Bright Box Theater USD 15 to 20

The Flying Ivories: Dueling Pianos (7PM SHOW) - ALL AGES

 Sat Jul 27 2024 at 07:00 pm Bright Box Theater USD 18 to 22

Tommy Prine w/ Special Guest Kindred Valley

 Sun Jul 21 2024 at 07:00 pm 186 North Loudoun Street, Winchester, VA

MSV at Night

 Fri Jun 28 2024 at 05:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Joe Martin at Bried Family Vineyards

 Sat Aug 03 2024 at 03:00 pm Briedé Family Vineyards

Silverada w/ Brennan Edwards & Monday Blues and special guest Zac Townsend

 Sat Aug 24 2024 at 07:00 pm Bright Box Theater USD 20 to 25

The Band of Heathens w/ TBD

 Fri Aug 09 2024 at 08:00 pm Bright Box Theater

Joe Martin at Briede Family Vineyards

 Thu Jul 04 2024 at 03:00 pm Briedé Family Vineyards

An Evening with Frank Solivan & Dirty Kitchen

 Fri Jul 26 2024 at 08:00 pm Bright Box Theater USD 22 to 25

Bottle Shock @ Briede Family Vineyards

 Sat Jul 06 2024 at 03:00 pm Briedé Family Vineyards

Market at the Hospital

Wed Jun 26 2024 at 11:00 am Winchester Medical Center

Market at the hospital

Wed Jul 03 2024 at 11:00 am Winchester Medical Center

Market at the Hospital

Wed Jul 17 2024 at 11:00 am Winchester Medical Center

Market at the hospital

Wed Aug 07 2024 at 11:00 am Winchester Medical Center

Market at the hospital

Wed Jul 31 2024 at 11:00 am Winchester Medical Center

Market at the hospital

Wed Aug 14 2024 at 11:00 am Winchester Medical Center

MSV at Night

 Fri Jul 26 2024 at 05:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

The Band of Heathens w/ TBD

 Fri Aug 09 2024 at 08:00 pm Bright Box Theater USD 30 to 35

Tony Logue & The 184 w/ Clint Park

 Fri Oct 18 2024 at 08:00 pm Bright Box Theater USD 15 to 20

🍉🍷 WATERMELON WINE FEST 2024!

 Sat Aug 24 2024 at 12:00 pm James Charles Winery & Vineyard

Grey Matter Splatter, Pain!, The Doo Wutz, I Defeat I @Blue Fox Billiards

 Fri Jul 19 2024 at 07:00 pm Blue Fox Billiards, Bar and Grill

The Fly Birds Acoustic Show at Purple Fern

 Fri Jul 12 2024 at 07:30 pm 3 South Loudoun Street , Winchester, VA, United States, Virginia 22601

Find Waldo Local 2024 LAUNCH

 Mon Jul 01 2024 at 10:00 am 7 N Loudoun St, Winchester, VA, United States, Virginia 22601

Granny's Comedy Kitchen feat. Zack Hammond, Ellen Doyle, Marc Hoover

 Fri Aug 02 2024 at 09:00 pm Granny's Place

FIND WALDO LOCAL PARTY!

 Wed Jul 31 2024 at 06:00 pm 7 N Loudoun St, Winchester, VA, United States, Virginia 22601

THE TAYLOR PARTY: CRUEL SUMMER TOUR - 18 & OVER

 Sat Nov 02 2024 at 09:00 pm Bright Box Theater USD 22 to 25

An Evening with The Nighthawks

 Fri Sep 20 2024 at 08:00 pm Bright Box Theater USD 18 to 22

Bright Box Comedy: Rob Maher [9:30PM SHOW]

 Sat Jun 29 2024 at 09:30 pm Bright Box Theater USD 15 to 18

Melody Trucks & The Fitzkee Brothers Band w/ TBD

 Fri Jul 19 2024 at 07:30 pm Bright Box Theater USD 15 to 20

Bright Box Comedy: Rob Maher [7PM SHOW]

 Sat Jun 29 2024 at 07:00 pm Bright Box Theater USD 15 to 20

Joey Harkum (Solo) LIVE at Bright Box

 Fri Sep 27 2024 at 08:00 pm Bright Box Theater USD 18 to 23

The Reflex: The Ultimate 80's Tribute Band - 18+

 Fri Nov 29 2024 at 09:00 pm Bright Box Theater USD 15 to 18

TELL ME LIES - The Fleetwood Mac Experience

 Fri Nov 15 2024 at 08:00 pm Bright Box Theater USD 28 to 33