Our fat-free, dolphin-safe Milwaukee events calendar is chock-full of things to do, but only a handful of events are worthy of the lofty honor of “Record Recommended” (patent pending). Here are our recommendations for June 20-26, 2022.

MONDAY, JUNE 20

Tour of America’s Dairyland: Cafe Centraal Bay View Classic @ Bay View
Since 2009, the Tour of America’s Dairyland has brought its wildly entertaining competitive road cycling series to various southeastern Wisconsin neighborhoods. This year, the 11-day series includes a number of Milwaukee and Milwaukee-area stops: Bay View (Monday), West Allis (Tuesday), Brady Street (Thursday), Shorewood (Friday), Downer Avenue (Saturday), and Wauwatosa (Sunday). Expect men and women’s pro races, kid races, plenty of food and drink, and plenty of blocked-off streets.

TUESDAY, JUNE 21

Chill On The Hill: Milwaukee Symphony Orchestra @ Humboldt Park
Chill On The Hill’s 17th season—which kicked off June 7—features a total of 13 weeks worth of free, family-friendly entertainment. Like last year, Chill has expanded its footprint by designating the space between the band chalet and the Vine Beer Garden for show-goers. The ever-popular concert series continues its 2022 season on Tuesday with a performance by the Milwaukee Symphony Orchestra. Go find your lawn chairs, break out your comfiest blanket, and put some beverages in the cooler.

Josh Groban @ American Family Insurance Amphitheater

Tour of America’s Dairyland: West Allis Cheese Wheel Classic @ West Allis

WEDNESDAY, JUNE 22

Tosa Tonight: Them Coulee Boys + Listening Party @ Hart Park
Since 2000, the Tosa Tonight summer concert series has brought free and family-friendly live music to Rotary Performance Pavilion in Wauwatosa’s Hart Park. Following a pandemic-prompted hiatus in 2020, the series returned in the summer of 2021. Thankfully, Tosa Tonight is back again in full force this summer. The series kicks off tonight with Them Coulee Boys and Listening Party.

THURSDAY, JUNE 23

Summerfest (Week 1) @ Henry Maier Festival Park (through June 25)
Hey! Summerfest 2022 is set for three consecutive Thursday-Friday-Saturday blocks: June 23-25, June 30 – July 2, and July 7-9. There are currently no plans for mask or vaccine requirements (unlike 2021’s not-very-packed-but-eminently-enjoyable, almost-in-the-fall installment). Click HERE for the full schedule, with dates, times, and stages!

Third Space Presents: Maxwell James @ Third Space Brewing
Every Thursday through September 15, “Third Space Presents” brings a different musical act to the Menomonee Valley brewery’s new and improved outdoor patio. In addition to the concert (which runs from 6-8 p.m., including an intermission) and plenty of award-winning local beer on site, Triciclo Peru is always on hand to serve empanadas and other Peruvian goodies out of its food truck. Tonight’s installment features music from Maxwell James.

Lara Beitz @ Milwaukee Improv
Milwaukee-born and -raised comedian Lara Beitz (who is now based on Los Angeles) returns to her old stomping grounds June 23-26 to headline a total of four shows at the Milwaukee Improv in nearby Brookfield. In recent years, the homegrown humorist has earned acclaim from Judd Apatow and David Spade, and has become the go-to feature act for Pete Holmes.

Laney Lou & The Bird Dogs + Joseph Huber @ Anodyne Walker’s Point Roastery

Tour of America’s Dairyland: Brady Street @ Brady Street

FRIDAY, JUNE 24

Greek Fest @ Wisconsin State Fair Park (through June 26)
Organized by the Annunciation Greek Orthodox Church, Greek Fest typically boasts gyros and other spit-roasted meats, delicious Greek desserts, Greek music and dancers, games and rides, a Greek marketplace, and much more. In 2020 and 2021, COVID-19 concerns caused organizers to transition the 55th and 56th annual events into a “Greek Fest Drive Thru.” This year’s installment will also feature a Whole Greek Chicken Drive Thru all three days. There will also be live performances by Vintage Groove, Sugar Bowl, The First Wave, and Six Pack Sammy. Best yet, admission is free!

Joshua Ray Walker + Sarah Shook & The Disarmers, Aaron Vance @ Cactus Club
If you don’t know the name Joshua Ray Walker yet, you’re about to be hearing a lot about him. Since first gaining notoriety in country music circles with his 2018 debut Wish You Were Here, the Dallas singer-songwriter has won fans all around the world and earned high praise from some of music’s most renowned publications. Walker’s sophomore album, Glad You Made It, has garnered even more acclaim and finds the up-and-coming country talent on the cusp of even bigger and better things. Tonight, Walker will be joined by Sarah Shook & The Disarmers, who return to Cactus Club a few months removed from the release of their latest album, Nightroamer.

Milwaukee Boat Line Concert Cruise: Master Of Puppets @ Milwaukee Boat Line
Despite the dozens of festivals, block parties, and weekly outdoor music series taking place on Milwaukee soil every summer, Milwaukee Boat Line sees fit to extend the city’s celebratory spirit to the water with its annual Concert Cruise series. Every Friday night between early June and the end of August, a variety of Wisconsin bands board the Vista King to perform on the lake vessel’s poop deck while the beer and pre-mixed margaritas flow liberally from 9-11 p.m. The series continues this week with a performance by Metallica tribute band Master Of Puppets.

Tour of America’s Dairyland: Shorewood Criterium Cycling Classic @ Shorewood

Lara Beitz @ Milwaukee Improv

SATURDAY, JUNE 25

Ruth B8r Ginsburg Presents: Creative Dissent For Reproductive Freedom @ South Shore Park / Cactus Club
Milwaukee’s femme-led force of nature and music, Ruth B8r Ginsburg, has long served as a beacon for homegrown activism, speaking truth to power and sounding incredible while doing it. Now, with seemingly EVERYTHING going to hell, the eight-piece outfit is organizing a “Creative Dissent for Reproductive Freedom.” The event will begin at noon in South Shore Park, where the group will lead a roughly half-mile parade to the Cactus Club. There, from 1-4 p.m., a fundraiser will be held featuring a makers market, a food truck, tables from various reproductive freedom groups, speakers, and musical performances from Sunshine Raynebow, LaRosette, Izzy Veta, and, of course, Ruth B8r Ginsburg.

Gigs 4 Good: Caley Conway @ The Tonic Tavern
Last summer, The Tonic Tavern celebrated its 12th anniversary with a new charitable music series. “Gigs 4 Good” featured a wide range of Milwaukee musicians performing at Tonic on select Saturdays. It went so well, Tonic is bringing it back for 2022! Like last time around, proceeds from the concerts (brought in through audience donations and from the bar donating a portion of that night’s sales) will benefit Milwaukee Center For Children And Youth, Bay View Community Center, and The Women’s Center. The series concludes tonight with a performance from the one and only Caley Conway.

LUXI (record release) + Gentleman Speaker, Griff, North Warren (solo set) @ Bremen Cafe

Pretty Guardian Gala @ Hyatt Regency Milwaukee

John Doe + Liv Mueller @ Shank Hall

Radkey + Beaker, Lunar Moth @ Cactus Club

Tour of America’s Dairyland: Otto Wenz Cafe Hollander Downer Classic @ Downer Avenue

Lara Beitz @ Milwaukee Improv

SUNDAY, JUNE 26

Jay Anderson + B-Free, Quinten Farr, Dave Schoepke, John Simmons @ The Jazz Estate
Former Milwaukee jazz musician Jay Anderson has been calling New Orleans home for the past few years; any chance to catch him back on his home turf, therefore, is a welcome one. For this double-set show, Anderson will “meet up with his old friends and show off his new singing voice.” Those old friends include the always stellar B~Free. Don’t miss this one!

Margarita Fest @ Deer District

Tour of America’s Dairyland: Cafe Hollander Tosa Village Classic @ Wauwatosa

Lara Beitz @ Milwaukee Improv

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