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2025 MUSIC LINEUP

FRIDAY

North Stage

Ted Leo and the Pharmacists

9:00PM North Stage

Ted Leo is one of the finest songwriters of his generation whether with his ‘90s power-pop group Chisel, his duo, The Both with Aimee Mann, or with his current, long-running band The Pharmacists, who will be in tow with him at Square Roots, Ted never lets the listener down.

Verböten

7:15PM North Stage

Verböten formed in 1982 by four kids ages 10 to 14. The Evanston punk rock band’s scrappy and aggressive songs made them young stalwarts of the burgeoning Chicagoland punk scene. Though they only lasted a year and a half, their legacy still endures: Dave Grohl, of Nirvana and Foo Fighters, says witnessing their band inspired him to start writing songs. Now, 41 years after they disbanded, they’ve reunited to release their debut album and to perform live shows.

Official Claire

5:30PM North Stage

One of Chicago’s finest new songwriters, Official Claire works with calm confession, deep wit, and the details of a poet. The Chicago Reader praised her combination of “sensitivity and straight talk”, and her music caught the attention of former Wilco member, LeRoy Bach. Her live band features Bach, as well as Brooks Hannon and Jake Keenum of Crisis Actress.

SOUTH STAGE

Los Vicios de Papá

8:15PM South Stage

Los Vicios de Papá drops immigrant beat with a passion for reggae, ska, and cumbia with lyrics that stem from the undocumented youth experience. LVDP was born out of a crumbling public education system and failing immigration policy in Chicago's Back of the Yards hood.

Lester Rey

6:45PM South Stage

Blending salsa with shatta flows, reggaeton with boleros, and gritty club bass with Caribbean melodies, Lester Rey pushes boundaries, creating music that both honors tradition and embraces innovation. His voice - equal parts crooning, chanteo, and fearless experimentation - channels the complex realities of identity, love, and survival in a post-colonial matrix.

Minor Moon

5:15PM South Stage

Minor Moon is the songwriting project of Chicago-based musician Sam Cantor. Conjuring elements of J.J. Cale, Grizzly Bear and Judee Sill, the band’s latest album, The Light Up Waltz, takes a big-hearted and kaleidoscopic lens to apocalyptic themes. "deeply adventurous… a sharp, reflective eye on the rearview mirror” (Pop Matters).

SATURDAY

North Stage

Calexico

9:00PM North Stage

Calexico’s Joey Burns and John Convertino return with their hopeful, kaleidoscopic beacon of rock, bluesy ruminations and Latin American sounds channeling cherished memories of Southwestern landscapes and joyful barrio melting pots into an evocative love letter to the desert borderlands that nourished them for over 20 years.

Mekons

6:45PM North Stage

Mekons, formed in 1977 Leeds, England, have an improbable history - a surprising & influential embrace of folk and country music with occasional forays into the art world. Their mind-boggling output blurs the lines between high and low art while remaining bold, unpredictable, and true to the punk ethos.

Cedric Burnside

4:45PM North Stage

Cedric Burnside’s life on the road began at age 13, drumming for his grandfather, the pioneering bluesman R.L. Burnside. His sound draws on the polyrhythmic, droning sound of the Hill Country Blues style, with its unpredictable chord progressions and bar counts, as well as from West African music. Burnside is a recipient of a National Heritage Fellowship, the country’s highest honor in the folk and traditional arts.

Big Sandy & His Fly-Rite Boys

2:45PM North Stage

Since forming in 1988 in Southern California, Big Sandy & His Fly Rite Boys have become one of the worlds most beloved Americana/Roots acts, drawing from the deep musical waters that flow just beneath the surface of Rock & Roll’s fertile soil. A childhood passion for country, doo wop, and rhythm & blues 45s led Sandy to pursue a singing career as a teenager, beginning a life in music that continues decades later.

Classic Country Ensemble

1:00PM North Stage

Old Town School’s Classic County Ensemble kicks off the music on the North Stage with some good ol’ good ones from the Country & Western canon.

SOUTH STAGE

Cesar Rosas & The Chi-Town Playboys

8:00PM South Stage

Cesar Rosas is a founding member of the iconic band, Los Lobos. Founded in 1973, the six-time Grammy winning band has spanned generations with traditional flavored music to mind altering sounds and garnered a reputation as being one of the best damn bands in America. Joining Cesar will be The Chi-Town Playboys featuring Chicago’s own Dave Herrero, Scott Tipping, Ari Seder, Dan Ingenthron, and Gerald Dowd.

¿Qiensave?

5:45PM South Stage

¿Qiensave? is a Cumbia Urbana group from Salinas, California with roots stretching back to Michoacán, Mexico. They create high energy dance music that has fortunately blessed them with the opportunity to travel throughout California, Arizona, Mexico, Colombia, and beyond.

Dill Costa

3:45PM South Stage

Raised in Rio de Janeiro, Dill Costa is one of Chicago’s best samba instructors and performers representing the authentic Carnaval tradition that is part of Brazil’s rich musical legacy. Catch her dynamic performance on the South Stage!

Los Gallos

2:00PM South Stage

Los Gallos are Chicago’s premier Mexi-Americana Roots band. Transcending musical borders, Los Gallos are known for their unsegregated sound. Their roots-oriented style draws upon traditional Latin and American vibes. Los Gallos seamlessly fuse an eclectic mix of cumbia, Tex-Mex, and bolero with country, rock and blues to create their signature sound.

Growing Boys

12:30PM South Stage

Growing Boys is a Chicago-based alternative folk band rooted in the bond of two best friends. Through tight harmonies and tender melodies, they blend nostalgia and playfulness - an open invitation to anyone in need of comfort or connection.

MAURER HALL

Cosmic Country Showcase

9:30PM MAURER HALL

Inspired by traditional country variety shows like the Grand Ole Opry, the Cosmic Country Showcase offers a unique live entertainment experience with an extraterrestrial-psychedelic twist hosted by country crooner Andrew Sa, and anti-host, comedian Mary Williamson.

Tobacco City

7:30PM MAURER HALL

Built out of a mutual love of classic and cosmic country, the members of Tobacco City bring their psychedelic and folk influences to the exploding genre. The result is a feel good sway that fits into modern urban modes and passes by the shrewdest of classic country heads. Simple songs and melodies built around nostalgic and blue stories. “...recalls Emmylou Harris and Gram Parsons at their most incandescent.” - Aquarium Drunkard

Dusk

5:30PM MAURER HALL

Dusk draws influence from rock & roll, rhythm & blues, country & western, and even the polkas from their homeland of Wisconsin. They bring with them a strong, informed, melodic statement that draws a line between themselves and the trend of bubble gum pop and country-influenced mall schlock.

Brandon Good

3:30PM MAURER HALL

Brandon Good is a Chicago artist with a penchant for Country music nodding to a wide range of notable genre influences while remaining true to the dance hall and honky-tonk heritage he loves.

Local Memory

1:45PM MAURER HALL

Local Memory is a six-piece indie/alt-country band from Chicago led by songwriter Amy Myers and collaborator Matt Ciani, joined by guitarist Lucas Chamberlain, drummer Nico Ciani, pianist Nicole Murray, and vocalist Lydia Cash. The band's latest EP "Greatest Hits" was released on May 30th and is available on all streaming services.

Second Half

12:30PM MAURER HALL

Join us for the time-honored Old Town School tradition, Second Half! Bring an instrument to play or just your voices. All are welcome to attend and join in.

FAMILY STAGE

The Dreamtree Shakers

4:30PM FAMILY STAGE

With Jeremy Babcock on guitar and vocals, Mani Bances on flute and saxophone, and Lenny Marsh on drums, each Dreamtree Shakers performance is a magical event full of stories from the sea, the circus, your own backyard and beyond that are sure to inspire your imagination.

Jonas, Anna & Company

3:30PM FAMILY STAGE

Teen String Band instructors, Jonas Friddle and Anna Jacobson, perform alongside Old Town School students.

Clamor & Lace Noise Brigade

2:30PM FAMILY STAGE

Clamor & Lace Noise Brigade is Chicago’s first glam street marching band composed solely of musicians and performers of marginalized genders at the forefront of Chicago’s brass band scene. Clamor & Lace collaborates to create joyful, raucous, and high-energy performances that promote female and non-binary composers.

Cooper Dual Language Mariachi Ensemble

1:30PM FAMILY STAGE

Enjoy the exciting and celebratory sounds of mariachi music as performed by the young kids in the Cooper Dual Language Mariachi Ensemble!

Wiggleworms with Anne-Marie & Amanda

12:30PM FAMILY STAGE

Since 1985, Old Town School of Folk Music’s Wiggleworms has been a popular rite of passage in Chicago - a music class for kids and caregivers that inspires new learning and sets the foundation for a lifelong love of music.

EAST LOBBY

Intro to Flamenco Dance with Maya Tatiana

4:00PM EAST LOBBY

Immerse yourself in the art of Flamenco with a workshop that blends traditional techniques, expressive movement, and the excitement of student performance.

Family Dance Party with Julianne Rice

3:00PM EAST LOBBY

Bring the whole family together for Family Dance, a joyful and interactive experience that’s all about having fun, moving together, and making memories with your loved ones.

Intro to Tango Dancing with Eduardo Villalba

2:00PM EAST LOBBY

No partner required! Experience the elegance and passion of Tango in this introductory class. Learn the foundational steps, then enjoy the chance to practice and dance, immersing yourself in the authentic spirit of Argentine Tango.

RESOURCE CENTER

Pop Up Record Sale

1-4PM RESOURCE CENTER

Hundreds of pre-owned LP records and CDs for sale! Proceeds benefit the Old Town School Resource Center library.

Pick-it-up: The History of Ska Music with Amanda Payne

1:30PM RESOURCE CENTER

Old Town School teaching artist Amanda Payne will share her ska playlists and talk about the history of ska music from Jamaica to English Two Tone and how its legacy shaped the New Tone movement today. With roots in American jazz and rhythm and blues ska pre-dates reggae and had a major influence on punk & pop rock. Ska is currently experiencing a renaissance, don't miss it!

SUNDAY

North Stage

Alejandro Escovedo

8:00PM North Stage

A celebrated singer and songwriter, Alejandro Escovedo has as eclectic a background and body of work as any rock artist of his generation. “Escovedo has blended the lyricism of Bruce Springsteen and Jackson Browne with the raw power of the Stooges and the Velvet Underground...the result is music with heart, brains, and a burning sense of adventure.” - Rolling Stone

The Lone Bellow

6:00PM North Stage

The Lone Bellow’s sound is made up of lush harmonies, heartfelt lyrics, and genre-blurring arrangements steeped in folk, rock, and gospel. Since their acclaimed 2013 debut the group has topped Americana charts, and headlined storied venues from Carnegie Hall to the Ryman Auditorium.

Natalie Bergman

4:15PM North Stage

The velvet voiced songstress from Chicago, Natalie Bergman, has a sound that is one part gospel, two parts classic soul, a half-cup of country, plus a healthy dash of the tree-top calls of woodland fauna, half remembered from a formative paradise. Whatever it is, these otherworldly strains of soul and gospel tinged disco-rock ’n’ roll melodrama are just what the doctor ordered.

Carnival Parade

3:00PM North Stage

Join in the fun and march alongside the Carnival Parade!

Le Winston Band

2:00PM North Stage

Le Winston Band is a one-of-a-kind Montreal based ensemble that blends its French-Canadian roots with Zydeco and Cajun music into a sound that is derived from both the rich musical traditions of Louisiana and their own identity as Montrealers. The group has been sharing their joie de vivre with audiences across the world.

Groove Time Trio

12:15PM North Stage

Groove Time is a percussion group based in Chicago, featuring Lenny Marsh, Mani Bances, and Mars Caulton. Along with a wide variety of drums and percussion instruments, they also use ukulele, saxophone, flute and vocals, for a family-friendly blend of world music and American folk songs.

SOUTH STAGE

Heartless Bastards

7:00PM South Stage

With a warm patchwork of rock ‘n’ roll, psychedelia, folk, alternative, and blues, Heartless Bastards unlock healing and catharsis within their music. Whether in the studio or on stage, the Austin-based band fronted by vocalist, songwriter, multi-instrumentalist, and producer Erika Wennerstrom calm as they captivate.

The Ike Reilly Assassination

5:00PM South Stage

Ike Reilly is a punk-poet-troubadour and the leader of the ferocious musical outfit The Ike Reilly Assassination. The former doorman and gravedigger hailing from the seemingly idyllic town of Libertyville, Illinois is the subject of the award-winning documentary Don’t Turn Your Back On Friday Night from executive producer Tom Morello.

Radio Free Honduras

3:00PM South Stage

Radio Free Honduras is a diverse collective of Chicago musicians, all united under one goal - supporting the artistry of Charlie Baran and bringing this tremendous talent into the spotlight where it belongs.

Hannah Frey

1:15PM South Stage

Hannah Frey is a Chicago-based vocalist, songwriter, and instrumentalist whose sound is a melting pot of midwestern rural and urban influences. While some might call it folk, Americana, or indie pop, Hannah lovingly refers to the music she makes as rock music for sensitive people.

MAURER HALL

Karaoke with Jackie Jasperson

6:00PM MAURER HALL

Cool off in Maurer Hall and sing some of your favorite Karaoke songs with Old Town School teaching artist, Jackie Jasperson.

Summertime Beatles Songbag with Tommi Zender & Tom Ryan

5:00PM MAURER HALL

Join Tommi & Tom for some Fab Four summer classics!

String Band Ensemble Performance & Jam

3:45PM MAURER HALL

Enjoy the sounds of the Old Town School’s String Band Ensemble. Bring an instrument if you want to join in on the jam!

Teen Showcase with Lizzie and the Deeds and Girls on Film

2:00PM MAURER HALL

Hear what the Old Town School teens are up to at the Teen Showcase!

Second Half

1:30PM MAURER HALL

Join us for the time-honored Old Town School tradition, Second Half! Bring an instrument to play or just your voices. All are welcome to attend and join in.

FAMILY STAGE

Raging Chihuahuas

4:30PM FAMILY STAGE

Old Town School Youth Rock Ensemble returns to Square Roots!

Victoria Djembe & Friends

3:30PM FAMILY STAGE

Victoria Boateng is an autism advocate. Victoria was diagnosed with autism when she was three years old and couldn’t speak until she was 7 years old. Victoria uses her gift of djembe to inspire the autism community and women of all races, gender, and creed.

Amirah Sackett & Ahmed Zaghbouni

2:30PM FAMILY STAGE

Join international artists Amirah Sackett and Ahmed Zaghbouni, aka MR MiC, for a fun and energetic performance that combines the hip hop dance style of "Popping" with live ‘Beatboxing’.

Swiftie Sing-Along! with Alicia Lees

1:30PM FAMILY STAGE

Join us for a fun and dynamic Taylor Swift sing-along led by Old Town School teaching artist, Alicia Lees!

Wiggleworms: Around the World in Song

12:30PM FAMILY STAGE

Since 1985, Old Town School of Folk Music’s Wiggleworms has been a popular rite of passage in Chicago - a music class for kids and caregivers that inspires new learning and sets the foundation for a lifelong love of music.

EAST LOBBY

Dance Divas Dance Party with Ethan Kirschbaum

4:00PM EAST LOBBY

Dance to the latest hits and unleash your inner star with Dance Divas, a high-energy class full of flair, fun, and fabulous moves.

Line Dancing with Marchello Lee

2:00PM EAST LOBBY

Get your groove on with Line Dance! Learn the steps to classic and modern line dances in this fun, social, and energetic workshop.

West African Dance for Everybody with Idy Ciss

1:00PM EAST LOBBY

Celebrate the vibrant rhythms of West African Dance with live drumming by Josh Guy. This high-energy class invites kids and families to move, groove, and connect with cultural traditions.

RESOURCE CENTER

Pop Up Record Sale

1-4PM RESOURCE CENTER

Hundreds of pre-owned LP records and CDs for sale! Proceeds benefit the Old Town School Resource Center library.

Leadbelly and Big Bill: Parallel Paths with Bear Williams

1:30PM RESOURCE CENTER

Old Town School teaching artist and Chicago musician Bear Williams will combine live performance with his playlists of Leadbelly and Big Bill Broonzy for a deep dive into the life and work of these fascinating musical greats.