About 14,000 people spilled onto the streets of downtown Winnetka throughout Friday and Saturday for the Winnetka Music Festival, featuring headliners Trombone Shorty & Orleans Avenue and Father John Misty.
Celebrating 10 years of the festival, this year’s event spanned 30 acts across four stages and several genres, in addition to seven Just Listen Sessions, which spotlighted behind-the-scenes perspectives from performing artists, authors and music industry professionals.
The festival is a byproduct of co-founder Val Haller’s music discovery platform Valslist, which she founded in 2007. Haller said she created the platform to introduce new music to an older audience. As Valslist grew in popularity, she started hosting live performances in her house by emerging bands passing through Chicago.
“It really showed me people want live music, but they’re not always going downtown for a 10:30 headliner,” Haller said.
She said it was festival co-founder Scott Myers who suggested expanding her underground concert series to a full-fledged festival. The festival is now in its 10th year.
During Friday’s Just Listen Sessions, Haller conversed with Vermont-born rock artist Grace Potter, who complimented the audience’s attentiveness during her session.
“I truly feel like what an audience is there to do is not to make the performer feel safe, but to make sure that there is at least enough respect and vulnerability between the two people that it’s like we’re holding up a mirror in front of each other and finding love in the middle of all that,” Potter said. “That’s what creative spirits do for each other.”
Before Potter’s set, singer-songwriter Jonah Kagen delivered a stand-out performance, deftly alternating between an electric and acoustic guitar to capture the sounds of his alternative chart-topping music.
One highlight was Kagen’s “Krissy,” which intimately charts his mother’s life story, pulled from his 2025 debut studio album “Sunflowers and Leather.”
Later on the Main Stage, Potter covered Woody Guthrie’s folk anthem “This Land Is Your Land,” before noting that Chicago marks the beginning of Route 66. She then introduced “Mother Road,” the title track of her 2023 studio album, by highlighting Romeoville, Illinois, a suburb along the historic highway that earns a mention in the song.
After spotting a Romeoville native in the crowd, Potter launched into the track, blending country influences with her signature rock sound. Later in the set, she shed her jean jacket and introduced “Trespasser,” the forthcoming sister album to “Mother Road.”
She performed an unreleased song she described as “fresh off the presses” before transitioning into “Love Me Not,” the album’s gospel-infused lead single. The highlight of Potter’s set was “Something That I Want,” which she recorded for the 2010 animated film “Tangled.” This selection fit well with the festival’s family-friendly atmosphere.
Potter’s performance concluded beneath a striking sunset, as fans were undeterred by light rain ahead of Friday night’s headliner, Trombone Shorty & Orleans Avenue. During his performance, the New Orleans-based artist captivated festivalgoers with his skills on the trombone, keyboard and drums.
While the majority of his set was purely instrumental, the vocality of Shorty’s trombone was demonstrated by an unexpected cover of Green Day’s “Brain Stew,” which heightened the crowd’s energy. As the night progressed, the band explored several genres, including hip-hop and Latin music, all honoring the diverse musical heritage of the Big Easy.
Vermont-born rock artist Grace Potter teased her upcoming album, “Trespasser,” during her Friday evening set.
Saturday’s lineup featured a variety of performances, from country and folk to dance and electronic acts. The festival also offered a Family Stage with performances geared toward children, including by musician and educator Mr. Dave, who offers children’s music classes and lessons at Mr. Dave Music in Chicago.
Chicago-based acoustic band Big Sadie brought stunning harmonies and instrumentals to the festival’s Chapel Stage as light seeped in through The Winnetka Chapel’s vibrant stained glass windows.
Outside the festival, Valslist regularly hosts $5 concerts in the chapel, with acts ranging from bluegrass to indie rock bands. Haller said a mission of her concerts — and the festival — is to support emerging artists and create an “oasis” for touring acts.
Nashville-born singer-songwriter Lauren Watkins brought smooth vocals with a Southern twang to the Main Stage, introducing her song “Britches” by relating to the audience.
“No matter how old you get, mean girls are always gonna be around,” Watkins told the crowd. “You get to decide how you deal with them.”
Writing songs is Watkins’ way of dealing with antagonizing characters in her life, she said. The lyrics of “Britches” hurl biting criticism at a self-obsessed “mean girl,” only softened by Watkins’ sweet vocals and a catchy chorus.
Haller interviewed indie dance band Supertaste on Friday at the Just Listen Sessions ahead of the group’s Saturday performance where they grooved out on the Lincoln Stage. The infectious guitar riffs on their disco-infused song “Supernova” instantly got the crowd dancing.
In curating the lineup, Haller said she likes to have a wide variety of genres, and supporting emerging artists is a top priority for her. Popping in and out of sets and interviews on Saturday, she stopped to chat with artists taking their breaks backstage and thanked them for coming out to the festival.
“We take really good care of the artists, because they’re so tired on the road,” Haller said. “They stay with host families. We take care of them. I meet them all. I write them all a love letter that goes in a goodie bag for them.”
Haller said the festival hasn’t changed much since 2017, and that’s by design. She said she’s considered expanding the festival by permanently moving to a larger venue like the Skokie Playfields, where the festival was held in 2021, but she prefers to keep it in downtown Winnetka as a “boutique” festival embedded in the town.
“Our old tagline was ‘music around every corner,’” Haller said.
Local businesses and vendors at the festival sprawled down a bustling Lincoln Avenue, including Evanston restaurants La Cocinita and Stacked and Folded, which also has a Winnetka location on Lincoln Ave. Haller said the festival has also partnered with Evanston venue SPACE for the past few years.
As the setting sun painted the sky beautiful shades of pink, fans flocked to the Main Stage to watch headliner Misty close out the festival.
With his unmistakable long bushy beard, the indie rock singer-songwriter set an intimate, haunting tone with dim red and yellow stage lighting. Misty is well-known for his collaborations with artists including Beyoncé, Lana del Rey and Lady Gaga. His set featured dreamy instrumentals and gorgeous saxophone solos that had the crowd swaying. Festivalgoers sang along to Misty’s vivid, often satirical lyrics.
Misty jokingly told the crowd about an interaction he had with a stranger in Las Vegas who told him he looked like the character Marv from the movie “Home Alone,” which was famously shot in Winnetka for its exterior house scenes.
The sweet instrumentals of Misty’s songs almost mask his clever and sometimes shocking lyrics, such as on “Chateau Lobby #4 (in C for Two Virgins),” where Misty sings, “I wanna take you in the kitchen / Lift up your wedding dress someone was probably murdered in.”
Misty concluded his set with his 2016 feel-good hit “Real Love Baby,” which instantly had the crowd singing along and dancing with friends and family.
For Haller, a primary mission of the festival is to make live music accessible to residents and families on the North Shore.
“There’s so many young parents and young families, and even if they love live music, getting downtown, getting there, paying for it, paying for a sitter, it’s hard,” Haller said. “So we were like, ‘Let’s bring a really cool thing up to you.’”
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Email: [email protected]
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