Thursday, Sept. 1
Milwaukee Rally @ Multiple Locations
Labor Day weekends are loud in Milwaukee, thanks to the city’s largest annual motorcycle gathering, the Milwaukee Rally. Each year thousands of Harley-Davidson riders take the city for five days of events at Harley dealerships around the city, as well as the Harley-Davidson Museum. The weekend will feature live music from dozens of rock, country and cover bands, big group rides, a free tour of the Harley-Davidson factory, bike shows, motorcycle demos and more than a few events featuring bikinis and/or wet T-shirts. Performers this year include Lita Ford, Grand Funk Railroad, Kris Crow Band, Chasin’ Mason, Southbound, Josh Thompson, Rebel Grace, Bella Cain and The Love Monkeys. (Through Monday, Sept. 5)
Jazz in the Park: Charles Walker Band @ Cathedral Square Park, 5 p.m.
The Charles Walker Band is one of those groups best enjoyed outdoors. With their up-tempo hybrid of funk and soul, the Charles Walker Band have become staples of regional music festivals including the Waukesha BluesFest, where their lively performances bring crowds to their feet. Tonight the WAMI-nominated band plays what’s always one of the most bittersweet shows of the year: The final installment of the season’s Jazz in the Park concert series, another reminder that summer is quickly coming to a close.
Friday, Sept. 2
Lil Yachty @ The Rave, 8 p.m.
Like so many of rap’s newer crossover stars, from Fetty Wap and Rich Homie Quan to Lil Uzi Vert, Lil Yachty blurs the lines between rapping and singing. The 19-year-old Atlanta native sings in a leisurely, agreeably melodic croon, and since his breakout single “1 Night” crept its way onto rap radio this spring, he’s been everywhere, guesting on songs by Post Malone, D.R.A.M., Offset and Bankroll Mafia, and appearing with Young Thug on Chance The Rapper’s “Mixtape.” Like so many young rappers with the “Lil” prefix in their name, Yachty isn’t for everybody, but he knows his audience. “We are the youth!” he yells on the opener of his latest mixtape Summer Songs 2, later declaring himself the “king of the teens.”
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Bonnie Raitt w/ Richard Thompson Trio @ The Riverside Theater, 8 p.m.
The fire-haired woman behind the sassy hit “Something to Talk About” and the lasting piano ballad “I Can’t Make You Love Me,” groundbreaking blues vocalist and guitarist Bonnie Raitt returned to the studio after a seven-year hiatus for 2012’s Slipstream, her 19th album. Highlighted by a string of slow-burning weepers, the album showed that Raitt’s voice has lost none of its emotional force with age. Raitt didn’t make fans wait quite as long for her follow-up album, Dig in Deep, which she released this winter. Though it’s got its share of heavy moments, too, it’s a breezier, more rocking set than its predecessor, with a live-in-the-studio sound that was designed to showcase her crack backing band.
Paramount Blues Festival @ Coal Dock Park, Port Washington
When most people think of the blues, they think of cities like Chicago or Memphis, but unassuming Grafton, Wis., had a role in shaping the genre, too, through the village’s storied Depression-era Paramount recording studio, when acts such as Charley Patton and Henry Townsend were sent north from Chicago to record here. Townsend himself was honored in 2006 at the first festival commemorating the village’s eminent blues history, the Paramount Blues Festival, which continues to draw a strong lineup of blues performers from around the state and beyond. Highlights of this year’s three-day lineup include Shonn Hinton & Shotgun and Tommy Castro on Friday night; Steve Cohen, Davina & The Vagabonds and Mud Morganfield on Saturday; and Tim Castle’s Legends of Country, Billy Bon Scott and Whiskey of the Damned on Sunday. For the complete lineup, visit paramountmusic.org. (Through Sunday, Sept. 4.)
Saturday, Sept. 3
Gringo Star w/ Surgeons in Heat and Greatest Lakes @ Cactus Club, 9 p.m.
Atlanta rock ’n’ rollers Gringo Star pay punny homage to The Beatles with their moniker, but if anything the group owes more to The Kinks than the Fab Four—perhaps a band name riffing on Kinks drummer Mick Avory just didn’t have the same ring to it. The group’s 2008 debut All Y’All was loaded with tight harmonies, perky riffs and plenty of tambourine for maximum British Invasion nostalgia. The group is touring behind their highly rocking just-released latest album, The Sides and In Between.
Monday, Sept. 5
Laborfest @ Summerfest Grounds, noon
For many people, Labor Day is just a day off, one more chance to grill and take in the last gasps of summer. But for union members and activists, it’s more than that; it’s also a chance to celebrate the contributions that laborers and their unions have made to society while championing for better working conditions. Each year workers celebrate the cause at Laborfest, a free party and rally at the Summerfest grounds featuring food, music and children’s entertainment. It kicks off at noon and runs through 5 p.m. following an 11 a.m. parade from Zeidler Square leading to the grounds. Although President Obama won’t make an appearance, as he did memorably in 2014, given this year’s high-stakes presidential election there should be an especially fired-up crowd.
Wednesday, Sept. 7
The California Honeydrops @ Shank Hall, 8 p.m.
Lech Wierzynski, the singer, guitarist and trumpeter for the The California Honeydrops, could probably write a great autobiography one day. Wierzynski was born in Warsaw, Poland and his parents were political refugees, but one upside of his nomadic youth was that it exposed him to all kinds of musical styles. He eventually settled in Oakland, Calif., where he founded his party band, which pairs New Orleans jazz and funk with Delta blues, California R&B and southern funk. Their upbeat live shows have landed them prominent gigs with acts like Buddy Guy, Dr. John and the late legends B.B. King and Allen Toussaint.