1. Labor Day Weekend at the Harley-Davidson Museum
ALL WEEKEND | HARLEY DAVIDSON MUSEUM
Harley-Davidson’s Labor Day celebration kicks off on its museum campus Thursday, with an ’80s cover band performing and food for sale. On Saturday, pick up gear from the HR Factory Outlet during their weekend-long sale and stay for BBQ and Blues with Donna Woodall. The weekend wraps on Sunday with the Big Unit’s Poker Run ride to benefit the Fisher House Wisconsin. The ride begins at 11 a.m. at the museum and concludes at LUXE Golf in Franklin with a live concert.
2. Wisconsin Highland Games
ALL WEEKEND | WAUKESHA EXPO CENTER
Get your kilts ready because the Wisconsin Highland Games are back! This festival offers an array of events and vendors that celebrate all things Scottish. Learn the art of ax throwing, shop the Celtic marketplace and discover everything there is to do at the Highland Games. Tickets are $20, and children 12 and under can enter for free. You can buy your tickets here.
It’s time to pick your Milwaukee favorites for the year!
3. St. Francis Days
ALL WEEKEND | MILTON VRETENAR MEMORIAL PARK
Celebrate Labor Day weekend at the 60th annual St. Francis Days. There won’t be a shortage of live music and good food all weekend, plus carnival rides and a veteran’s parade on Saturday starting at 11 a.m. You can also sign up for the cornhole tournament online, and admission is free.
4. Oak Creek Lionsfest
ALL WEEKEND | 9327 S. SHEPARD AVE., OAK CREEK
Join the Oak Creek Lions Club this Labor Day weekend for live music, helicopter rides and carnival games for their annual summer celebration. The festival will offer three live music venues with performances all weekend. There will be deals all weekend, including free entry for seniors on Friday, free face painting and games on Saturday and a free meal for veterans on Monday. There will also be a car show on Sunday at 10 a.m.
5. The Cheap Shots at the Bud Pavilion
FRIDAY 6-10 P.M. | WISCONSIN STATE FAIR PARK
The Cheap Shots are performing at the Wisconsin State Fair Park Bud Pavilion this Saturday. The performance is free, and food and drink will be available for purchase at the fairgrounds. Gates open at 6 p.m., and the show starts at 7.
6. Don Omar ‘Back to Reggaeton’ Tour
FRIDAY AT 8 P.M. | FISERV FORUM
Reggaetonero-superstar Don Omar is performing at the Fiserv Forum this Friday as part of his 2024 “Back to Reggaeton” tour. Don’t miss the opportunity to catch the Puerto Rican rapper as he performs some of his most popular tracks. Tickets are available online now.
7. Rhythm and Soles 5K Walk-Run
SATURDAY 11 A.M. | VETERANS PARK
The Rhythm and Soles 5k is bringing together those who have been impacted by overdoses for International Overdose Awareness Day. This race will follow Milwaukee’s lakefront, starting at Veterans Park at 11 a.m. The event, which includes spoken tributes, will begin at 9:30 a.m. You can find free food, music and vendors at the finish line. Online registration is now open.
8. Boxing in the Beer Garden
SATURDAY FROM 5 P.M.-11 P.M. | DEER DISTRICT BEER GARDEN
This Saturday, you can relax with a beer and watch live professional boxing at The Beer Garden in the Deer District. Food and drinks will be available at this outdoor event as boxers go head-to-head in the ring. Tickets are available now.
9. Pitbull: Party After Dark Tour
SATURDAY AT 8 P.M. | AMERICAN FAMILY INSURANCE AMPHITHEATER
Grammy-winning singer Pitbull is returning to Milwaukee for his Party After Dark tour. The rapper and singer behind many international hits like “Fireball,” “Give Me Everything” and “Timber,” is performing on the Summerfest grounds. Tickets are available now. Dale.
10. Third Ward Art Festival
SATURDAY AND SUNDAY | BROADWAY ST.
The Third Ward Art Festival is a free festival celebrating 200 different artists from across the country. Artwork will be available for purchase, and the event will also include a painting class and live art demonstrations. There will also be a Kid-Friendly Art Tent for children to learn more about art. You can enjoy live music and plenty of food and drink options from the Third Ward’s many restaurants.
11. Maxwell Street Days
SUNDAY FROM 6 A.M.-2 P.M. | FIREMEN’S PARK
This Sunday, one of the four annual Maxwell Street Days is taking place in downtown Cedarburg. Located in Firemen’s Park, this festival includes hundreds of vendors selling anything from antiques to fresh produce to sports memorabilia. Admission is free and food and drink will be available for purchase.
12. Punk Rock Rummage Sale
SATURDAY FROM 11 A.M.-3 P.M. | X-RAY ARCADE
X-Ray Arcade in Cudahy is hosting a Punk Rock Rummage Sale this Saturday. From 12-3 p.m., you can explore collections of unique vintage pieces, vinyl and art. General admission is free, but you can pay a $2 early bird fee to arrive at 11 a.m. and find the best punk treasures before they’re gone.
13. Struggle Jennings With Huey Mack
SUNDAY 8 P.M. | THE RAVE
Rap-country artist Struggle Jennings is performing at The Rave this Sunday night at 8.
Struggle Jennings is the grandson of country icons Waylon Jennings and Jessi Colter and has appeared on songs alongside country sensation Jelly Roll. He will be joined on Sunday by country singer Huey Mack. Tickets are available now.
14. Laborfest
MONDAY FROM 11 A.M.-5 P.M. | HENRY MAIER FESTIVAL PARK
This free event, put on by the Milwaukee Area Labor Council on the Summerfest grounds features food and drink vendors, bingo, wrestling, a classic car show, live music, and children’s activities, too. Before the festival, the union members are marching in a parade Downtown, starting at Zeidler Union Square.
