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https://offsquaremusic.org/2025/06/sundays-on-the-square-features-meg-and-the-wheelers-august-10/
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Sundays on the Square features Meg and the Wheelers August 10! Meg and the Wheelers are a Country Western band from Chicago, Illinois, known for their unique blend of classic honky-tonk sound with modern lyrics and themes. This FREE performance is 5:00 – 7:00 pm CDT, and there’s more … read on!
One of the best things about summer in Woodstock — Sundays on the historic Woodstock Square, Cass & Van Buren Streets, Woodstock, IL 60098.
Five FREE summer concerts to enjoy outdoors on the Square with friends! These FREE concerts are 5-7 pm on the following Sundays:
June 29 – The Special Consensus
July 6 – Small Town
July 27 – Arranmore
August 10 – Meg and the Wheelers
August 24 – Kevin Purcell & The Root Doctors
If we end up with rain, the alternate site will be Unity Spiritual Center, at 225 W Calhoun St, Woodstock, IL 60098. Check back on this site for updates and / or confirmation.
And if you’re not already on our email list, sign up for our monthly emails that keep you up-to-date on all Off Square Music events.
So come on out to enjoy those lazy, crazy days of summer with Sundays on the Square, beginning with Sunday, June 29, 5:00 – 7:00 pm.
Sundays on the Square in 2025 – Food & Hempstock Pharms
In addition to our great lineup of bands playing from 5:00 – 7:00 pm, we have food and other perks for you. For these special Sundays, we have arranged these vendors:
June 29 – Karajo / Chow Down and CannaBus
July 6 – Karajo / Chow Down and CannaBus
July 27 – Sandie Dogs and CannaBus
August 10 – Karajo / Chow Down and CannaBus
August 24 – Sandie Dogs and CannaBus
Restaurants on the Square may be open on these evenings and will have carry-out items, but please confirm with specific places. Of course, you can bring your own food items as well!
Hempstock Pharms Products will be there with the CannaBus all five Sundays, selling a variety of cannabis products. Read what they say about their product HERE. And take a look at some of their products HERE.
Sunday Art in the Square
In conjunction with Off Square Music, a group of local artists will be selling their work on the Square on each of the Sundays listed above, from 4:00 – 7:00 pm.
While you enjoy listening to some amazing music, you will have the chance to browse and buy some beautiful art! The artists will have functional, sculptural work and so much more in between!
Sponsored by the Clayworkers’ Guild of Illinois and the City of Woodstock.
Meg and the Wheelers … About
Meg and the Wheelers are a Chicago-based country-western band known for their unique blend of classic honky-tonk sound with modern lyrics and themes.
Band Members:
Megan Sampson: Vocals and rhythm guitar, the frontwoman and songwriter
Matt Ciani: Drums
Brian Weakly: Bass
Will Phalen: Lead guitar and pedal steel
Amy Myers: Backup vocals
Their Story:
Meg and the Wheelers officially formed in 2018. Megan Sampson, the band’s frontwoman, grew up immersed in country music, influenced by her father who played in Western bands. Sampson met Rob Winn, a college friend, who became a founding member of the band after seeing her perform karaoke. The band’s debut performance was at a block party in Winn’s neighborhood. Will Phalen, who later became their producer and pedal steel player, was also a part of this initial gathering.
Meg and the Wheelers are known for their blend of sharp-witted lyrics, solid harmonies, and classic steel guitar twang, infused with themes of love, loss, and the shared experience of country music. Their influences include Loretta Lynn and Margo Price. They’ve released an EP titled “Bar in the Divorce” and their latest EP “Midwest Best” was recorded at the legendary Electrical Audio studio in Chicago and released in 2023. The band has shared the stage with national acts like Ashley McBryde and Joshua Hedley. They were voted the Second City’s 2nd favorite Country Band by the Chicago Reader’s Best of 2024 reader poll.
See also:
Fitzgeralds Nightclub
Hunter Peebles
Carol’s Pub
The Deli
Here’s a music sample from Meg and the Wheelers to enjoy:
Meg and the Wheelers perform 'Jared' Gems in the Rough 2023 contest
Find out more about Meg and the Wheelers here:
From Block Club Chicago: “‘Meg And The Wheelers’ Unique Brand Of Honky-Tonk Sounds Right At Home In Chicago…
“Cowgirls and cowboys can check out their music on Bandcamp, Apple and Tidal — including 2019’s EP ‘Bar in the Divorce’ and the recent release of ‘Midwest Best’.” (From Block Club Chicago – fun and informative article!)
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We appreciate your contributions in support of music in Woodstock. You may contribute to Off Square Music and also to specific performers using the buttons in the left column of most pages on this site.
Sundays on the Square
Brought to you by…
These FREE summer concerts are brought to you by Off Square Music, the Woodstock Opera House, the City of Woodstock, and the Woodstock Hotel/Motel Tax Grants to the Arts — as well as your generous donations. It truly takes a village!
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