Entertainment events in Woodstock

Check out happening entertainment events all around Woodstock, IL

✨ 2026 McHenry County Fair ✨

 Tue, 04 Aug at 06:00 am 11900 Country Club Road, Woodstock, IL, United States, Illinois 60098

Woodstock PrideFest 2026

 Sun, 14 Jun at 11:00 am Woodstock Square Historic District

Struggle Jennings in Mchenry

 Fri, 05 Jun at 07:00 pm The Vixen

Vicki Peterson & John Cowsill

 Fri, 24 Apr at 06:00 pm Woodstock Opera House

Heartache Tonight

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

2026 Woodstock Folk Festival / Spring Benefit Concert – Upcoming!

 Sun, 19 Jul at 12:00 pm Woodstock Square

Cirque Us at Woodstock Opera House

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

Theatre 121's Rock of Ages

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

Rock of Ages

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

Stevie McVie

 Sat, 16 May at 07:30 pm 121 West Van Buren Street Woodstock, IL 60098

Dragon's Days Out

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

Levi Kreis at Woodstock Opera House

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

Atlys in Woodstock

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

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

Ride for the Heroes

 Sun, 17 May at 08:30 am Woodstock Harley-Davidson

David Maraniss

 Wed, 15 Apr at 06:00 pm Woodstock Opera House

It's Complicated - Film

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

Lebowski Fest

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

Cinco de Mayo Dinner

 Tue, 05 May at 06:00 pm 140 Cass St, Woodstock, IL, United States, Illinois 60098

5th Annual Thunderfest

 Sat, 25 Apr at 05:30 pm Offsides Sports Bar & Grill

Stage Left Cafe & Off Square Music

 Fri, 03 Apr at 07:00 pm Stage Left Cafe

Songs of the Skies and Seas: A Musical Journey

 Sun, 03 May at 03:00 pm Woodstock Opera House

It's Complicated at Woodstock Opera House

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

World Peace Day

 Sat, 12 Sep at 02:30 pm Woodstock Square Historic District Free

Ladies Night April: Burlesque Salon

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

Frida: Viva La Vida

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

Ladies Night June: Prohibition

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

Double Treble Dueling Pianos @ Private Fundraising Event

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

Live Psychic Mediumship Event

 Wed, 06 May at 07:00 pm Classic Cinemas Woodstock XQ

Mantra Music Kirtan with Ananda Lila Kirtan

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

Macyn’s Jars 2nd Anniversary Party!!!

 Sat, 25 Apr at 11:00 am Macyn’s Jars