Some seasonal entertainment offerings come and go, while some become icons. Mandatory Milwaukee is all about the latter. This week: Chill On The Hill (and other recurring local concerts).

Though Milwaukee’s spring and summer festival season is officially underway, the city and its surrounding suburbs have yet to kick off any of its weekly outdoor live music happenings. That all changes tonight when Chill On The Hill returns to Humboldt Park for its 20th anniversary season.

Yes, this evening’s appearance by the likes of Grim Paddle, Louie & The Flash Bombs, and Bright Eyed & Blind beneath the park’s band shell will start the series in style. Following tonight’s show, there will be Chill On The Hill installments each and every Tuesday through August 26. In all, there will be an varied blend of 26 local acts taking part in a total of 13 concerts.

As if a free weekly concert at one of Milwaukee County’s largest and most beloved parks isn’t already enticing enough on its own, Chill attendees are allowed to carry-in their own foods and beverages to enjoy while lounging in their lawn chair or whilst sprawled out on a blanket. And if you don’t feel like lugging a cooler or bringing your own snacks, Chill On The Hill has beverages (including beer from Lakefront Brewery) available for purchase and food truck vendors parked on-site.

The food trucks open at 5 p.m. and the concerts begin promptly at 6:30 p.m. Yes, you are allowed to bring your dog (if it’s kept on a short leash) and no, you’re not allowed to smoke or vape. Milwaukee is extremely lucky to have a series like Chill On The Hill. Whether you attend tonight or go another time (or various other times, for that matter), you should really try to make it out to Humboldt Park on Tuesdays this summer.

While it’s one of the largest, most established, and longest-running of its kind in the region, Chill On The Hill is just one of many recurring outdoor music happenings that help make the Milwaukee area so special each and every spring/summer. Just look at our list of summertime entertainment undertakings and you’ll get an idea of just how many different recurring weekly music series we have in our midst. Honestly, you could go to at least one every day between now and early September. If you have doubts about that, let’s just run through an abbreviated weekly schedule quick.

Mondays

Musical Mondays @ Lake Park

Tuesdays

Chill On The Hill @ Humboldt Park
Riverwalk Commons Series @ Riverwalk Commons

Wednesdays

Tosa Tonight @ Hart Park
Washington Park Wednesdays @ Washington Park
Wonderful Wednesdays @ Lake Park
MKE River Round-Up @ Milwaukee River
Heart(beats) Of The City @ Red Arrow Park

Thursdays

Thursday Bike Night Concert Series @ Harley-Davidson Museum
Under the Bridge @ Third Space Brewing
Jazz In The Park @ Cathedral Square Park
Tunes @ Noon @ 411 East Wisconsin Center Courtyard

Fridays

Current Sounds @ Lakefront Brewery

Saturdays

South Shore Farmers Market @ South Shore Park
Current Sounds @ Lakefront Brewery

Sundays

Summer Patio Series @ Great Lakes Distillery
Sopra Mare @ Villa Terrace Museum & Garden

That’s honestly just a partial list of the numerous weekly music series that will be happening in the area between now and the end of the summer. And we didn’t even include any festivals, fairs, or monthly music offerings here. There’s so, SO much to be seen and heard in and around Milwaukee this spring and summer, and it really kicks off tonight with Chill On The Hill. Get out there an enjoy it!

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.