When the Wisconsin winter finally thaws away for good (so, approximately yesterday), everything comes back to life, from the green scenery to the streets and sidewalks. And in the few months of sun and splendor we have, we do our damnedest to fill all those spaces with music. 

This city and its surrounding areas host dozens of free outdoor live music series, each one with something special to offer beyond the stage. Jazz in the Park brings the Downtown bustle. Concerts in the Garden delivers a beautifully serene setting. Washington Park Wednesdays provide an unpredictably diverse music lineup (plus that gorgeous band shell) while Wednesday Night Lives at State Fair bring the ruckus. 

And Chill on the Hill brings all of the above – which is why, for me, it’s the finest of the free summer live music series flock.

I was admittedly a late-comer to Chill on the Hill – partly because I was a late-comer to live music just in general. (Idiot Young Matt spent most of his childhood thinking, “Why would I see a musician or band sound worse than they do recorded?” – an opinion that makes a lot more sense when you consider my first taste of live music was Smash Mouth.) Thankfully, my music taste evolved along with my palate for live performance. And along the way, I moved to Bay View and found my way to the annual Humboldt Park hullabaloo – this year running June 7 through Aug. 30. After all, can’t complain about the price – and two hours later, I couldn’t complain about much else either, turning Chill on the Hill into a fast regular for any summer plans.

As the ostensible star of the show, the local music lineup is always strong, typically finding a tremendous balance between booking familiar favorites and keeping its fingers to the pulse of young rising stars across genres. And as with most summer events, the Tuesday night shows are a treat for the taste buds as much as the ear drums, with several food trucks parked just off the side of the hill (one meal from Braise’s food truck still deliciously haunts me years later – so yes, if it’s in attendance, ten out of ten would recommend) along with boozy drinks from the nearby beer and wine garden. And if none of that somehow suits your fancy, you can always bring in your own snacks and sips, turning a casual concert night into an impromptu craft beer sampling session. 

That’s all great – but that’s all nothing out of the ordinary for a good Milwaukee live music series. What makes Chill on the Hill exemplary is that essential 2020s element: vibes. 

Even on a colder Tuesday night, there’s just something warm about the energy emanating from the Humboldt Park hill setting. It’s not the most serene setting or the most high-energy or the most eye-catching – instead it’s a little bit of all of that at once. Plus, there’s something wonderful about climbing up the modest hill and suddenly overlooking the crowd gathered together, giving me flashbacks to memories of County Stadium, of walking up the small hallway ramp to the seats and watching the giant stadium and pure green field gradually reveal itself. 

Sure, that sounds melodramatically romantic – but Chill on the Hill is the kind of Milwaukee event you feel melodramatically romantic about. 

And that’s all before I reach the true best part, the source of those almighty vibes mentioned before: the people. That warmth coming from the park isn’t just the music or the grills going in the food trucks, but the community gathered together. It’s the kind of place that the phrase “Smallwaukee” was born for – the loving definition, not the condescending one. Everyone seems to know everyone on the hill – and if they don’t, they’re about to. Everyone’s in a mood to say hi or catch up on the neighborhood news or simply greet one another’s pet. (A key Chill on the Hill benefit: prime pupper-watching conditions.) 

Over the years, I personally have used Chill on the Hill multiple times as a friend group meshing point, family meeting friends meeting college friends meeting neighbors. And each time, it ends with me looking around at these former strangers turned deep conversation buddies – one bunch talking their latest craft beer discoveries, another talking streaming stuff, another comparing work notes, all with a perfect soundtrack of live local music guiding things in the background.

I no longer live in Bay View – but when I return for this concert series in the summer, I always feel like I never left. No matter where you’re from, at Chill on the Hill, you’re instantly a neighbor. And these days, that’s a feeling Milwaukee – and everywhere – could use more of.