Entertainment events in Woodstock

Check out happening entertainment events all around Woodstock, IL

Grease Sing-a-long at Woodstock Opera House

 Fri, 13 Feb at 07:00 pm Woodstock Opera House

Grease - A Movie Sing-A-Long

 Fri, 13 Feb at 07:00 pm 121 Van Buren St. Woodstock, IL 60098

Theatre 121's Singin' in the Rain

 Fri, 20 Feb at 07:30 pm 121 Van Buren St. Woodstock, IL 60098

Neil Diamond - The Tribute

 Sat, 07 Mar at 02:00 pm 121 Van Buren St. Woodstock, IL 60098

Vicki Peterson & John Cowsill

 Fri, 24 Apr Woodstock Opera House

Heartache Tonight

 Sat, 09 May at 07:30 pm 121 Van Buren St. Woodstock, IL 60098

Singin in the Rain at Woodstock Opera House

 Sun, 01 Mar at 02:00 pm Woodstock Opera House

Woodstock Chamber 2026 Annual Gala - An Evening of Mystery & Excellence

 Fri, 13 Mar at 06:00 pm 101 N Johnson St, Woodstock, IL 60098-3258, United States

Rock of Ages

 Thu, 18 Jun at 06:00 pm Woodstock Opera House

Theatre 121's Rock of Ages

 Fri, 19 Jun at 07:30 pm 121 Van Buren St. Woodstock, IL 60098

Dragon's Days Out

 Sat, 30 May at 10:00 am Mchenry County Fairgrounds

Empress Acoustic Duo at Nikos Woodstock

 Sat, 21 Feb at 07:00 pm Nikos Red Mill Tavern

Cirque Us at Woodstock Opera House

 Sat, 11 Apr at 03:00 pm Woodstock Opera House

Levi Kreis at Woodstock Opera House

 Sun, 19 Apr at 03:00 pm Woodstock Opera House

Pearlsnap at Shamrocked Woodstock, IL!

 Sat, 14 Mar at 05:15 pm Woodstock Square

OSM presents Claudia Schmidt in concert

 Fri, 06 Feb at 07:00 pm Stage Left Cafe

Rock of Ages at Woodstock Opera House

 Sun, 28 Jun at 02:00 pm Woodstock Opera House

Casablanca - Film

 Tue, 14 Apr at 06:00 pm Woodstock Opera House

2026 Cinema Soup Film Festival

 Fri, 27 Mar at 12:00 pm Needful Things Shop

Ladies Night June: Prohibition

 Fri, 26 Jun at 07:00 pm 121 E Calhoun St USD 93

Lesson Plans to Late Night at the Woodstock Opera House

Fri, 06 Feb at 06:00 pm Woodstock Opera House

Atlys in Woodstock

 Mon, 20 Apr at 06:30 pm Woodstock North High School

An Intimate Evening with Mira Sorvino

 Fri, 06 Mar at 07:30 pm 121 Van Buren St. Woodstock, IL 60098

Valentine's Painting Party at Stage Left (Woodstock Square)

 Wed, 04 Feb at 05:30 pm The Stage Left Cafe USD 35

Backcountry Discovery Routes MTBDR Screening: Woodstock Triumph

 Sun, 15 Feb at 02:00 pm Woodstock Triumph Free

First Fridays - In Concert Series

 Fri, 06 Mar at 07:00 pm Stage Left

From Grit to Greatness, FHPC's 30th Anniversary Soiree!

 Thu, 12 Mar at 05:30 pm 110 N Johnson St, Woodstock, IL 60098, United States

Valentine's Dinner with Elaine Dame

 Thu, 12 Feb at 06:30 pm 140 Cass St, Woodstock, IL, United States, Illinois 60098

Creative Living Series: Joseph Luzzi

 Thu, 19 Mar at 10:00 am 121 Van Buren St. Woodstock, IL 60098

MTBDR Expedition Documentary Film Premiere

 Sun, 15 Feb at 02:00 pm 2235 S Eastwood Dr, Woodstock, IL, United States, Illinois 60098

David Maraniss

 Wed, 15 Apr Woodstock Opera House

Ladies Night April: Burlesque Salon

 Fri, 24 Apr at 07:00 pm 121 E Calhoun St USD 93

It's Complicated - Film

 Tue, 19 May at 06:00 pm Woodstock Opera House

It's Complicated at Woodstock Opera House

 Wed, 20 May at 01:00 pm Woodstock Opera House

Close Call Band

 Sat, 07 Feb at 08:00 pm 1330 S Eastwood Dr, Woodstock, IL, United States, Illinois 60098

Valentine's Paint & Sip (Bull Valley / Woodstock Studio)

 Sat, 14 Feb at 06:45 pm 10016 Bull Valley Rd USD 35

Struggle Jennings in Mchenry

 Fri, 05 Jun at 07:00 pm The Vixen

Paint and Sip: Horse Themed Painting Party!

 Sat, 28 Feb at 01:00 pm 10016 Bull Valley Rd USD 37

The Bucket List

 Tue, 17 Mar at 06:00 pm Woodstock Opera House

Frida: Viva La Vida

 Wed, 22 Apr at 01:00 pm 121 Van Buren St. Woodstock, IL 60098

Double Treble Dueling Pianos @ Private Fundraising Event

 Sat, 25 Apr at 06:30 pm Offsides Sports Bar & Grill

Mantra Music Kirtan with Ananda Lila Kirtan

 Sat, 30 May at 07:00 pm Blue Lotus Buddhist Temple Woodstock USD 27

Krysten Knievel @ Niko's Red Mill Tavern

 Sat, 14 Feb at 06:30 pm Nikos Red Mill Tavern

Lebowski Fest

 Sat, 18 Apr at 08:00 pm Kingston Lanes Bowling and Sports Lounge

PILLOWTALK

 Wed, 18 Feb at 07:00 pm Woodstock Opera House