Entertainment events in Winston Salem

Check out happening entertainment events all around Winston Salem, NC

Winston-Salem Oktoberfest 2025

 Sat, 27 Sep at 04:00 pm Winston-Salem USD 7 to 31

2nd Annual Downtown Witches Walk & Winston "the Other" Salem Night Market

Fri, 24 Oct at 06:00 pm 545 N Trade St. Unit 100, Winston-Salem, NC, United States, North Carolina 27101

Wise Man Oktoberfest

Sat, 20 Sep at 12:00 pm Wise Man Brewing

2025 Moonlight Madness 5K, Monster Mile & Fun Run

 Sat, 06 Sep at 06:30 pm Bailey Park

Winston-Salem Official Halloween Bar Crawl

 Fri, 31 Oct at 05:00 pm Winston-Salem USD 15 to 36

Winston-Salem Day of The Dead Bar Crawl - Dia De Muertos

 Sat, 01 Nov at 04:00 pm Winston-Salem USD 15 to 31

UNDERGROUND PRESENTS FREAKY FRIDAY CRIMSON PEEK

 Fri, 12 Sep at 08:00 pm Monstercade

Angelo's Artisan Fall Market

 Sun, 07 Sep at 12:00 pm Wise Man Brewing

NC COMEDY FEST AT MARKETPLACE CINEMAS

 Fri, 12 Sep at 08:00 pm Marketplace Cinemas Winston Salem USD 11

Innovation & Cinema: Little Shop of Horrors

 Fri, 10 Oct at 07:00 pm Bailey Park

UNCSA Jazz Ensemble: Big Band!

 Sat, 27 Sep at 07:30 pm 1533 S Main St, 27127

BunFest2025

 Sat, 20 Sep at 11:00 am Winston Junction Market

The Canary Affair

 Sat, 13 Sep at 04:00 pm 1027 Rock Knoll Ct unit 215 USD 55

Kyle Caudle & Timberline | Evan Blackerby

 Thu, 18 Sep at 08:00 pm Gas Hill Drinking Room

Wise Man Brewing Fall Festival

 Sat, 18 Oct at 08:00 am Wise Man Brewing

Innovation & Cinema: La Bamba

 Fri, 12 Sep at 07:00 pm Bailey Park

Bobby Boy Bakeshop presents Pierce Pettis!

 Sat, 06 Sep at 07:00 pm Bobby Boy Bakeshop, 845 S Poplar St, Winston-Salem, NC 27101

BunFest

 Sat, 20 Sep at 11:00 am Winston Junction Market USD 5 to 55

Ears to the Ground

 Sat, 13 Sep at 07:00 pm Wise Man Brewing

Dan Tyminski Band

 Fri, 17 Oct at 08:00 pm The Ramkat

Boos, Brews, and Booze Halloween Bash

 Fri, 31 Oct at 08:00 am Wise Man Brewing

Class of 1990 South Stokes High School Reunion

 Sat, 20 Sep at 05:30 pm Historic Brookstown Inn USD 45

Songs From The Road Band

 Fri, 12 Sep at 07:00 pm 626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101

Pure Fiyah Reggae Band

 Sat, 06 Sep at 07:00 pm Wise Man Brewing

Ben Folds in Concert

 Sat, 11 Oct at 07:30 pm RJ Reynolds Auditorium

Shmack Daniel’s debut at Millers on Trade

 Fri, 05 Sep at 09:00 pm Miller's on Trade

AML Wrestling presents Eye For An Eye

 Sat, 27 Sep at 05:00 pm Benton Convention Center

Salsa Dance at the Coal Pit

 Fri, 26 Sep at 07:00 pm Incendiary Brewing Company

Tyler Dodson / Sam Lewis

 Sat, 25 Oct at 07:00 pm 626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101

Lakeside Concert: Bob Mould & J. Robbins

 Sat, 27 Sep at 07:00 pm 750 Marguerite Dr, Winston-Salem, NC, United States, North Carolina 27106

Artistic Elements Showcase

 Fri, 12 Sep at 06:00 pm NCMA Winston-Salem (formerly SECCA) Free

FREE Beginner Line Dance Lessons - Wise Man Brewing

 Sat, 27 Sep at 06:00 pm Wise Man Brewing

Niall McCabe / Victoria Victoria

 Thu, 18 Sep at 07:00 pm 626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101

The Ocean Blue | Brian Tighe (The Hang Ups)

 Fri, 12 Sep at 08:00 pm The Ramkat

Winston Salem State University Homecoming Concert at Lawrence Joel Veterans Memorial Coliseum

 Fri, 17 Oct at 06:00 pm Lawrence Joel Veterans Memorial Coliseum

Winston-Salem Halloween Bar Crawl

 Sat, 25 Oct at 04:00 pm Winston-Salem USD 15 to 36

Ghoul Moon Festival 3

 Sat, 25 Oct at 04:00 pm West Salem Art Hotel

Pepe Aguilar

 Fri, 17 Oct at 07:00 pm Lawrence Joel Veterans Memorial Coliseum

The Ocean Blue

 Thu, 11 Sep at 07:00 pm The Ramkat

Latin Dancing Nights at AFAS

 Sat, 13 Sep at 07:00 pm 630 N Liberty Street, Winston-Salem, NC, United States, North Carolina 27101

Triad Embrace: Bachata, Kizomba, Zouk dance social

 Sat, 06 Sep at 07:30 pm AFAS - Art for Art's Sake

Bailey Beats: DaShawn Hickman

 Sat, 20 Sep at 05:00 pm Bailey Park

The Machine at The Ramkat

 Wed, 17 Sep at 08:00 pm The Ramkat

Bailey Beats: Sam Fribush Organ Trio

 Sat, 18 Oct at 05:00 pm Bailey Park

Kitchen Dwellers | Pressing Strings

 Sun, 02 Nov at 07:00 pm The Ramkat

Emo Night Karaoke Winston Salem at Hoots Beer Co. | 9/26/25

 Fri, 26 Sep at 08:00 pm Hoots Beer Co.

Forsyth Woman 20th Anniversary Party

 Thu, 18 Sep at 06:00 pm The Crest USD 45

NC COMEDY FEST AT MARKETPLACE CINEMAS

 Sat, 13 Sep at 08:00 pm Marketplace Cinemas Winston Salem USD 11

Jeffrey Dean Foster | James Mastro | Ava Foster

 Sat, 20 Sep at 08:00 pm Gas Hill Drinking Room

Marsalis + Tchaikovsky

 Sat, 20 Sep at 07:30 pm RJ Reynolds Auditorium

Feyleux / Idol Talk / Cold Choir - 9/6/2025 Hoots

 Sat, 06 Sep at 08:00 pm Hoots Beer Co.

Daniel Donatos at The Ramkat

 Thu, 02 Oct at 08:00 pm The Ramkat

The Ocean Blue at The Ramkat

 Fri, 12 Sep The Ramkat

ART CRUSH

 Fri, 19 Sep at 07:00 pm Downtown Arts District, Winston-Salem

Wilmington Color Run By Color Craze

 Sat, 18 Oct at 09:00 am Wilmington, North Carolina

East Nash Grass | AJ Lee & Blue Summit!

 Sun, 09 Nov at 07:00 pm The Ramkat

John Moreland at The Ramkat

 Tue, 16 Sep at 08:00 pm The Ramkat

Firefly Market - Brown Mountain Lightning Bugs

 Sat, 13 Sep at 12:00 pm Footnote Coffee & Cocktails (Footnote Coffee & Cocktails)

Winston-Salem Color Run By Color Craze

 Sat, 18 Oct at 09:00 am Winston Salem, North Carolina

Hiroya Tsukamoto

 Fri, 14 Nov at 07:00 pm 626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101

Samantha Fish

 Thu, 02 Oct at 07:00 pm The Ramkat

Apple Festival

 Sat, 27 Sep at 10:00 am Historic Bethabara Park

Reynolda's Community Day

 Sat, 20 Sep at 09:30 am 2250 Reynolda Rd, Winston-Salem, NC, United States, North Carolina 27106

Daniel Donato's Cosmic Country

 Wed, 01 Oct at 07:00 pm The Ramkat

Tucker's Tap Yard - Brown Mountain Lightning Bugs

 Fri, 10 Oct at 06:00 pm Tucker's Tap Yard

Banna: Halfway to St. Paddy's Day!

 Fri, 12 Sep at 07:00 pm Wise Man Brewing

Illuminare

 Sun, 26 Oct at 05:00 pm Centenary United Methodist Church

Renaissance Night, presented by the Carolina Renaissance Festival

Sat, 06 Sep at 06:30 pm 951 Ballpark Way, Winston-Salem, NC, United States, North Carolina 27101

Contra Dance - IN WINSTON-SALEM!! *FIFTH TUESDAY*

 Tue, 30 Sep at 07:00 pm Knollwood Baptist Church

FREE Intro to Pro Wrestling Training Class

 Sun, 05 Oct at 01:00 pm 4421 North Cherry Street, Winston-Salem, NC

Crane & Co Returns to Miller's On Trade

 Sat, 13 Sep at 09:00 pm Miller's on Trade

Line Dance Night - East of Texas

 Fri, 26 Sep at 08:00 pm East of Texas

Winston-Salem New Years Eve Bar Crawl

 Wed, 31 Dec at 06:00 pm Winston-Salem USD 0 to 46

2025 Carver High School Alumni Band & Parade

 Fri, 12 Sep at 04:00 pm Carver High School USD 0 to 39

A Book Talk with Stephanie Perkins

 Fri, 10 Oct at 06:30 pm Bookmarks USD 0 to 36

Ardmore Art Walk 2025

 Sat, 08 Nov at 11:00 am 501 Miller St

Winston-Salem Color Craze Run

 Sat, 18 Oct at 09:00 am Winston-Salem

Samantha Fish at The Ramkat

 Fri, 03 Oct at 08:00 pm The Ramkat

Flamenco Night with Ed Stephenson

 Sun, 07 Sep at 06:00 pm Manolo's Boutique Wines & Bistro USD 23 to 39

Matt Kendrick's Hall of Fame Celebration with The Matt Kendrick Trio and The Sirens of Jazz

 Fri, 19 Sep at 08:00 pm The Ramkat

Dan Tyminski

 Thu, 16 Oct at 07:00 pm The Ramkat

Meet Wrestling Superstar Santino Marella- Live at Wrestlecade Fanfest!

 Sat, 29 Nov at 10:00 am Wrestlecade Fan Fest - Benton Convention Center USD 13 to 55

Max and Heather Stalling

 Sun, 19 Oct at 02:00 pm 626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101

Flying High Again - The Ultimate Ozzy Osbourne Tribute Experience

 Fri, 31 Oct at 08:00 pm The Ramkat

Charles Latham and the Borrowed Band | rofessor Twang and the Honky Tonk Review

 Sat, 13 Sep at 08:00 pm Gas Hill Drinking Room

The Old Faith, Hope, and Charity

 Fri, 19 Sep at 07:30 pm 4401 Indiana Ave, Winston-Salem, NC

Carrie Welling with special guest Tiffany Thompson

 Fri, 17 Oct at 07:00 pm 626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101

RAGTOP BETTY | 9/12/25 | MILLER'S ON TRADE

 Fri, 12 Sep at 09:00 pm 622 Trade Street, 27101

Bassoon and Friends - Ofrenda

 Sat, 01 Nov at 07:30 pm 1533 S Main St, 27127

Paint with your Labubu!

 Sat, 06 Sep at 01:00 pm Wine & Design (Winston-Salem, NC)

Crossroads #033: Pokey LaFarge & DJ Faby Baby

 Sun, 12 Oct at 06:00 pm 750 Marguerite Dr, Winston-Salem, NC, United States, North Carolina 27106

Bob Mould

 Fri, 26 Sep at 07:00 pm Southeastern Center For Contemporary Art

HELLA STELLAR | 9/19/25 | MILLER'S ON TRADE

 Fri, 19 Sep at 09:00 pm 622 Trade Street, 27101

Junction Bazaar

 Sat, 13 Sep at 11:00 am 901 N Trade, Downtown Winston-Salem, NC, United States, North Carolina 27101

Dan Tyminski Band at The Ramkat

 Fri, 17 Oct at 08:00 pm The Ramkat

Mikyung Sung, double bass in Recital

 Sat, 04 Oct at 04:00 pm 1533 S Main St, 27127

The Official Halloween Bar Crawl (Fri & Sat) - Winston-Salem

 Fri, 31 Oct at 04:00 pm Bar La Chingada USD 14 to 20

The Sacred Veil

 Sat, 08 Nov at 07:30 pm Wake Forest University

TopHouse at The Ramkat

 Thu, 13 Nov The Ramkat

Peter Holsapple | Walter Salas-Humara

 Wed, 24 Sep at 08:00 pm Gas Hill Drinking Room