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Latest Posts
  • [ June 28, 2025 ] Sundays on the Square features Smalltown U.S.A. July 6! Concerts
  • [ June 28, 2025 ] Julie Monroe featured Saturday July 12, 2025 | Stage Left Open Mic – DATE CHANGE! Open Mics
  • [ June 28, 2025 ] All-Original Open Mic July 25, 2025 All-Original Open Mic at Stage Left Cafe
  • [ June 28, 2025 ] Sundays on the Square Features Arranmore July 27, 2025 Concerts
  • [ June 27, 2025 ] Scott Engstrom is featured Friday August 8 2025 | Stage Left Open Mic Open Mics
HomeConcerts

Concerts

Off Square Music sponsors several types of concerts and concert series.

These concerts feature touring musicians and bands and are held at Stage Left Cafe, 125 Van Buren St., Woodstock. Most concerts begin at 7:00 pm. Details and ticket links for each concert will be posted on our website and Facebook page.

If you enjoy great music and fun times out in Woodstock with friends, we welcome you to join us!

Keep an eye on this page. Details and updates about each upcoming event will be posted below as the date approaches.

Smalltown U.S.A.
Concerts

Sundays on the Square features Smalltown U.S.A. July 6!

June 28, 2025 0

Sundays on the Square features Smalltown U.S.A. July 6! FREE, 5-7 pm, historic Woodstock Square, Cass & Van Buren, Woodstock, IL. […]

Arranmore has Irish roots, but is reaching out for diversity in a mix of variety of styles on its fifth and latest release, the engaging 'Memories that Echo' - Chicago Tribune
Concerts

Sundays on the Square Features Arranmore July 27, 2025

June 28, 2025 0

Sundays on the Square features Arranmore, July 27, 2025, 5:00 – 7:00 pm. Join with friends and family to celebrate summer in Woodstock! […]

Meg and the Wheelers are a Country Western band from Chicago, Illinois.
Concerts

Sundays on the Square features Meg and the Wheelers August 10

June 27, 2025 0

Sundays on the Square features Meg and the Wheelers August 10! Country Western band with classic honky-tonk sound, modern lyrics and themes. […]

Kevin Purcell and the Root Doctors
Concerts

Sundays on the Square features Kevin Purcell and the Root Doctors August 24

June 27, 2025 0

Sundays on the Square features Kevin Purcell and the Root Doctors! Woodstock, IL, on the Square, 5-7 pm, FREE concert. […]

SongSisters: Patti Shaffner, Amy Dixon-Kolar, Sue Fink.
1st Friday Concerts

SongSisters Perform Friday, June 6, 2025 | 1st Friday Concert

May 28, 2025 0

SongSisters perform Friday June 6, 2025, 1st Friday Concert. Stage Left Cafe, 125 E. Van Buren, Woodstock, IL. 7pm CDT (open 6:30pm). […]

Special Consensus Bluegrarss Band
Concerts

Sundays on the Square features The Special Consensus June 29

May 28, 2025 0

Sundays on the Square features The Special Consensus June 29! FREE, 5-7 pm, historic Woodstock Square, Cass & Van Buren, Woodstock, IL. […]

Sundays on the Square
Concerts

Sundays on the Square 2025 | Season Schedule

April 26, 2025 0

Sundays on the Square 2025 run 6/29, 7/6, 7/20, 8/10, 8/24. Great bands, FREE, 5-7 pm, Woodstock Square, Cass & Van Buren, Woodstock IL. […]

The Stage Leftovers back at Stage Left Cafe. Come on out to enjoy a great performance!
1st Friday Concerts

StageLeftovers Perform Friday, May 2, 2025 | 1st Friday Concert

April 1, 2025 0

StageLeftovers perform Friday May 2, 2025, 1st Friday Concert. Stage Left Cafe, 125 E. Van Buren, Woodstock, IL. 7pm CDT (open 6:30pm). […]

Ken Johnson performs Friday, April 4, 2025 First Friday Concert, Stage Left Cafe, Woodstock, Illinois.
1st Friday Concerts

Ken Johnson Performs Friday, April 4, 2025 | 1st Friday Concert

March 29, 2025 0

Ken Johnson performs Friday, April 4, 2025. Come on out to hear him live at Stage Left Cafe, Woodstock, IL, at 7 pm CST. […]

Bad Penny is an acoustic trio based in the northwest suburbs of Chicago. They have fast become one of the most popular performing groups at the Woodstock Farmers Market.
1st Friday Concerts

Bad Penny Featured Friday, March 7, 2025 Winter Concert (with special guest, Sam Jones)

March 1, 2025 0

Bad Penny is featured on Friday, March 7, 2025. Come on out to hear them live at Stage Left Cafe, Woodstock, IL, at 7 pm CST. […]

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Special Recognition

Judy Matzen and Keith John perform together at the Mast House.
Honors

Judy Matzen – A Friend to All, Loved By All

January 24, 2022 3

Judy Matzen is probably the main reason Off Square Music exists today. The Woodstock music community loved Judy, and she returned that love. […]

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