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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
HomeConcertsSundays On The Square

Sundays On The Square

Sundays on the Square in 2022 runs every Sunday, late June – early September, except for the third Sunday in July when the Woodstock Folk Festival is always scheduled.

Enjoy some great bands from 5:00 – 7:00 pm on the historic Woodstock Square, Cass & Van Buren Streets, Woodstock IL 60098. On June 26, though, we’ll kick off the season with music from noon to 7:00 pm as part of Woodstock’s Summer in the Park.

Shows vary, some with one and some with two acts, featuring local, regional, and national talent. Among the confirmed shows for this year are The Sons of the Never Wrong, Arranmore, Corner Boys, and Honey Cellar.

If a picnic isn’t on your agenda, restaurants located around the Square are generally open, but it’s a good idea to confirm with specific places.

Sunday evenings on the Square are always a memorable part of summer in the Woodstock area. Put the dates on your calendar now, and watch for updates and specifics on the bands as they come available. Better yet, subscribe to the calendar on this site (lower right corner of the calendar pages).

How to Perform at a Concert

Off Square Music invites and encourages local and non-local performers to perform in all our venues.

If you would like us to consider you for a concert, we ask that all current and future performers visit this page to complete a one-time informational form. Once you submit that form, you can return to the same page any time to request a performance spot in any of our venues.

Upcoming Sundays on the Square Events

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. […]

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. […]

Sundays on the Square featuring Square Notes with John Hegner & Friends | Sept. 1, last FREE 2024 concert. 5-7 pm CDT, Woodstock, IL.
Concerts

Sundays on the Square featuring Square Notes with John Hegner & Friends | Sept. 1 – RAIN OR SHINE

August 30, 2024 0

Sundays on the Square featuring Square Notes with John Hegner & Friends | Sept. 1, last FREE 2024 concert. 5-7 pm CDT, Woodstock, IL. […]

The Empty Pockets play a soulful, 70’s-inspired blend of exploratory grooves, shifting time signatures and distinctive vocals.
Concerts

Sundays on the Square Featuring The Empty Pockets | August 4 – RAIN OR SHINE

July 29, 2024 0

Sundays on the Square featuring The Empty Pockets | August 4, is 3rd in our 2024 season! FREE performance 5-7 pm CDT, Woodstock IL Square. […]

With meticulously crafted lyrics, captivating natural charisma, and an impressive assortment of instruments at their command, South for Winter have time and time again established themselves as a crowd favorite.
Concerts

Sundays on the Square featuring South for Winter | July 7 – INDOORS DUE TO RAIN

June 30, 2024 0

Sundays on the Square featuring South for Winter | July 7, 2nd in our 2024 season! 5:00 – 7:00 pm CDT, Woodstock historic Square. FREE! […]

Sundays on the Square
Concerts

Sundays on the Square 2024 | Season Schedule

June 1, 2024 1

Sundays on the Square in 2024 run 1st Sundays, 6/2-9/1. Enjoy great bands, all FREE, 5-7 pm, Woodstock Square, Cass & Van Buren, Woodstock IL. […]

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Special Recognition

Roger Benson
Honors

Tribute to Roger Benson

June 7, 2019 2

I met Roger at a fundraiser for the Masthouse in 2002.  A giant man in jeans and a leather vest outbid everyone for a German chocolate cake.  […]

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