Downtown Winnetka spent much of the June 19-20 weekend transformed into a multi-stage music extravaganza, drawing crowds from across the country to the North Shore for a milestone edition of the annual Winnetka Music Festival.
For its 10th anniversary, the two-day festival welcomed more than two dozen artists to the stage, with headliners Trombone Shorty & Orleans Avenue and Father John Misty performing alongside notable musical acts like Grace Potter, Jonah Kagen, Petey USA, Ben Kweller, Futurebirds and more.
Additional weekend festivities included a variety of family-friendly programming, exclusive listening sessions with select performers and numerous food and drink offerings from popular local vendors like Culinary Gangster, Happy Lobster, La Cocinita and Hofherr Meat Co.
“Come for the street fest, stay for the music,” festival co-founder Val Haller told Pioneer Press.
“Everybody likes music,” she added with a laugh, “but even if you have no interest, the food trucks, and the restaurants and just the ambience of hanging out in the streets, you could come for that alone.”
Haller started Winnetka Music Festival with her husband Mark Haller and co-founder and business partner Scott Myers in 2017. She said she wanted it to serve as a homegrown, local concert series for every musical taste.
With the help of sponsor and co-presenter SPACE Presents, the outdoor arm of the Evanston SPACE music venue, the event has grown to what it is now, Haller said, welcoming nearly 7,000 festival-goers a day to experience the “spirit of the Winnetka community.”
The festival is also supported by the Village of Winnetka, Winnetka Park District and the Winnetka Chamber of Commerce.
Haller, a lifelong concert lover and music fan, said the festival’s origins date back to the creation of her business Valslist, a music discovery platform she launched in 2007 to “solve an industry-wide problem” of getting new music to reach an older audience demographic.
“When iTunes launched in 2003, I just saw everybody, a lot of busy adults, my peers at the time..[fall] into an abyss, and they didn’t know how to consume music anymore, how to upload or download [songs], or all of the things that came with digital music,” Haller said.
“The music industry targets the 18 to 23 age demographic, but I’m like, ‘What about people older than that?’’
While all the big music companies were battling over what would be the next great iPod or MP3 player, Haller realized there was a gap in the market for how to reach new content on these devices.
“Once [people] know how to use the gadget, what are they putting on it, other than just their ‘oldies?’…for anybody who’s out in the work world, who isn’t spending all of their time on music anymore, they maybe need some help with just curation, or to filter out and find what they like.”
Haller’s website of curated playlists eventually evolved into the Valslist Radio app, and from there, intimate “listening room” concerts held in her living room for smaller artists and bands traveling through the Chicagoland area.
“I started this sort of underground house concert series here in Winnetka,” Haller remarked. “Who would ever think, like, in the suburbs?”
“It’s from those house concerts, honestly, that this festival was built,” she said.
Ten years later, the Winnetka Music Festival has grown to attract a plethora of household music names as well as up-and-coming artists looking to expand their audience reach.
Georgia native singer-songwriter Jonah Kagen, who performed on the event’s main stage on Friday, told Pioneer Press before his set that festivals like these are what he looks forward to playing at most.
“I love playing in or near Chicago, this is one of my favorite places to play ever,” said Kagen, who first became a viral hit among listeners for his 2024 breakout single, “God Needs a Devil,” which reached #1 on Billboard’s Alternative Airplay chart in May 2025.
“When we were talking about booking festivals this year, I really wanted to do festivals in front of people that are looking to find new music, who are obsessed with music and excited about music.”
Kagan often quells performance jitters by talking more to listeners in between songs, which he said often catches people off guard.
“I like to talk to people. I like to talk to the audience, mostly because I’m freaking out all the time, and it’s nice…headlining [a show] is serving your fans, this is like, ‘let’s go make some new ones’,” he added.
Musician Ben Kweller, who took the festival stage Saturday, told Pioneer Press “Winnetka Fest” is like a “little secret nationwide that not everybody knows about, but if you know, you know.”
Kweller said he has a long history of playing Chicago-area shows, but every performance brings something new.
His 2002 song, “Wasted & Ready,” first became a hit on Chicago radio and led to a sold-out tour for his debut album, “Sha Sha.”
“I just, I love Chicago and I’m psyched to do this festival,” he added.
Onstage, several artists nodded to Winnetka’s place in pop culture history, including headliner Father John Misty, who voiced during his Saturday night set, that “everybody keeps saying the Home Alone house is right by here, is that true?” (The iconic holiday movie home is located at 671 Lincoln Ave in Winnetka).
Just one block away from the lakefront on Lincoln Avenue and Elm Street, the festival weekend stood as a renowned destination for music lovers alike.
“I think this is just fabulous,” said Lauren Carron, a Winnetka resident who lives just a few blocks away from the closed-off festival grounds.
“Towns need to come together and do more of this type of thing,” said Carron, who brought her two grandchildren on Friday to experience their first-ever concert.
Kevin Braude, a Northbrook resident sporting a festival shirt from 2023, said he’s been coming to the Winnetka Music Festival for more than five years, but “every year it brings something great.”
“It just, it exposes up-and-coming indie bands and all kinds of bands to older people like me,” Braude said with a chuckle.
“And older people need to be exposed to this kind of music.”
