Apple Fest Entertainment

NORTH STAGE

Tunes throughout the day in the parking lot at Lawrence Ave.

Saturday, October 4^th 2025

10:00am - 12:00pm - The Bourbon Aristocracy, 100-Proof Bottled-In-Bond Bluegrass
The Bourbon Aristocracy's repertoire includes bluegrass classics from artists such as Bill Monroe, Lester Flatt and Earl Scruggs, Jimmy Martin, Del McCoury, Stanley Brothers, and many more - alongside more recent bluegrass favorites and songs by classic country artists like Hank Williams and Johnny Cash.

1:00pm - 3:00pm - SurfCycle, Garage Rock, Grunge, Surf, Punk
Apple Fest's longtime Stage Manager takes the stage with his own band of Prog Punkers and Space Surfers.

4:00pm - 6:00pm - Would You Kindly?, Powerful, Female Fronted, Alternative Rock
A captivating band from Kenosha, Would You Kindly? is known for their unique sound blending electric violin with modern rock, pop, and jazz.

*times subject to change

 

SOUTH STAGE
The parking lot at Lincoln & Sunnyside

Saturday, October 4^th 2025

9:30am - 11:00am - 14th Annual Pooch Costume Contest, by Urban Pooch Canine Life Center and Urban Pooch Training & Fitness
An amazingly fun opportunity to parade your special pooch in front of our special panel of judges in hope of winning great prizes and parading around Lincoln Square. (CLICK HERE TO REGISTER)

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SOUTH STAGE
KIDS ZONE 

Kids Activities at South Stage - Parking lot at 4513 N Lincoln

PRESENTED by OLD TOWN SCHOOL OF FOLK MUSIC
Hosted by Renée Nanzer

Saturday, October 4^th 2025 

11:30am - 12:05pm
Chello Grrove!, Hip-hop & Line Dance

12:25pm - 1:00pm
Wiggleworms, with Miss Julie

1:20pm - 1:55pm
Cielito Lindo Duo, Modern Mariachi

2:15pm - 2:50pm
K-Pop Demon Hunters Dance Party!, with Miss Katie

3:10pm - 3:45pm
Stephen Kuhn, Jazz for Families

4:05pm - 4:40pm
Festive Fall Fiddlin', with Stella & Anne-Marie

5:00pm - 5:35pm
The Amazing Adventures of 2NBs, Queer Musical Circus Show

NORTH STAGE

Tunes throughout the day in the parking lot at Lawrence Ave.

Sunday, October 5^th 2025

10:00am - 12:00pm - Diamondback, Country, Americana, Rock & Blues
Diamondback has been a popular staple of the Chicago Music scene for decades. Their extensive song list is truly a history of Country, and for that matter, American pop music, and promises something for everyone.

1:00pm - 3:00pm - Los Perros Cubanos, Music of Cuba's Golden Age
Los Perros Cubanos features the music of Cuba's Golden Age of the 1940s and 1950s. The band's music combines the traditional Cuban music styles of Son Cubano, Salsa, Cha Cha, and Charanga with modern instrumental prowess for a captivating sound that moves your feet.

4:00pm - 6:00pm - Jonas Friddle, Americana & Folk
Jonas Friddle is a gifted singer, songwriter & Old-Time banjo player with a collection of Chicago's finest players in his band. The music entertains as it deftly explores just about every nook & cranny of modern folk, from revivalist antique appropriation to protest songs to modern love songs. His tunes bear the marks of a musician who's done time in pubs & square dance halls.

*times subject to change

 

SOUTH STAGE
KIDS ZONE 

Kids Activities in the Parking Lot at 4513 N Lincoln Avenues
PRESENTED by TIMELESS TOYS
Hosted by Scottie Friedland

Sunday, October 5th 2025

10:00am - 10:45am
Magic Time, with Amazing Adamz

11:00am - 11:45am
Music Fun, with Leonardo Music

12:00pm - 12:45pm
Forest Fables: Storytime with Drag Queens, with Candi Forest

1:00pm - 1:45pm
Get Your Giggles Out, with Comedy Dance Chicago

2:00am - 2:45am
Chicago's Storytime Chamber Band for All Ages, with The Lucky Trikes

3:00pm - 3:45pm
Catch the Beat, with The Headspin Guy

4:00pm - 4:45pm
Get Your Sillies Out, with Comedy Dance Chicago

5:00pm - 5:45pm
Traditional Irish Music, with The Donnybrooks