River Challenge Glides Through Milwaukee
Plus: Oktoberfest, Beet Street Festival and more.
The Green Bay Packers have a bye week, but don’t fret – instead of game-day snacks, you can indulge in the traditional German bites at Milwaukee Oktoberfest. Instead of rooting for your favorite team, you can cheer on the cutest costume at the Brady Street Pet Parade. And if you need something a little more fast-paced, the Milwaukee River Challenge will see rowboats cruising along a three-mile route.
October 3-5: Milwaukee Oktoberfest
Who needs a beer? Milwaukee Oktoberfest has you more than covered. The annual festival will bring live music, entertainment, German traditions and plenty of beer to t Henry Maier Festival Park. This year’s Oktoberfest is a tribute to previous Milwaukee mayor Henry Maier’s love for German festivities – which was also his inspiration for creating the Henry Maier Festival Park and Summerfest. Join in on the fun by checking out the Miss Oktoberfest and Stein Hoisting competitions, and take in the cuteness at the Wiener Dog Pageant. The festival will also feature authentic German food provided by Kegel’s Inn. General Admission is $12 at the door. For more information, visit the Milwaukee Oktoberfest website.
October 4: Beet Street Fall Festival
Cactus Club’s annual Beet Street Fall Festival block party returns with another lineup of live music, vendors, food trucks and more. The festival will take place outside of the venue on the block of S. Wentworth Avenue north of E. Russell Avenue. This year’s lineup features performances by Fellow Kinsman, FTBK, Os Mutantes and more. The event will feature family-friendly activities like face painting and screen printing, and Palomino will host “The Great Midwestern Pie Championship.” Be sure to stick around for the afterparty, which will take place indoors at Cactus Club and will feature performances by Queen Meabh, Ninajirachi, Hitech and more. The festival is free to attend and will run from 1 p.m. to 7 p.m. The afterparty will run from 7 p.m. until 10 p.m.
October 4: Milwaukee River Challenge
High school, collegiate and club teams from throughout the Midwest region will race in row boats on the Milwaukee and Menomonee Rivers as part of the annual Milwaukee River Challenge. Racers will tackle a difficult three-mile course that passes through downtown Milwaukee, granting spectators multiple vantage points to watch the race. A running race commentary will be provided at Schlitz Park, where there will also be food and beverages for sale and the chance to hang out with participants. The race will begin at 9 a.m. For more information, visit the Milwaukee River Challenge website.
October 5: Brawl in the Beer Hall II: Poor Decisions
Legendary wrestler Stone Cold Steve Austin proved to us that wrestling and beer make a great combo, and Lakefront Brewery’s Brawl in the Beer Hall is an explosive marriage of the two. For one night, Lakefront Brewery will transform into a wrestling arena, featuring high-flying matches between Matt Cordona, Big Trouble Ben Bishop, Mad Dog Connelly and more. The brewery will serve food before and after the event, and will serve beverages throughout. The event is restricted to ages 21 and up and will feature adult themes and language. Doors will open at 5 p.m. and the action will begin at 7 p.m. For more information and to purchase tickets, visit Lakefront Brewery’s website.
October 3-5: Milwaukee Tattoo Arts Festival
If you’re looking to add to an existing collection of skin art or you’re itching to get your first tattoo, the Milwaukee Tattoo Arts Festival should be on your radar this weekend. Hundreds of tattoo artists from all over the world will set up at the festival with custom designs for guests to choose from. The festival will also feature live entertainment such as the Dead Man’s Carnival, sword swallowing, contortion artists and more. Each day, artists will enter the tattoos that they’ve done into a variety of competitions, and you can help bring home the gold by volunteering as a canvas. The Milwaukee Tattoo Arts Festival will take place at the Baird Center. Admission is $20 for a single day or $40 for the weekend. For more information and to purchase tickets, visit the Villain Arts website.
October 5: Brady Street Pet Parade
While Brady Street typically gets plenty of foot traffic on the weekend, this Sunday it will instead get lots of paw traffic. The annual Brady Street Pet Parade will bring pets of all breeds together for an afternoon of contests, live entertainment, pet-related vendors and more. Do you and your pet share an uncanny resemblance? Take part in the Pet & Owner Look-Alike contest. Does your furry friend know how to wow an audience with their moves? Enter them in the Best Trick contest. And don’t miss out on the parade, which will kick off at 1 p.m. The Brady Street Pet Parade will run from 11 a.m. to 4 p.m. All proceeds from the event will be donated to MADACC.
If you think stories like this are important, become a member of Urban Milwaukee and help support real, independent journalism. Plus you get some cool added benefits.
Entertainment Preview
-
Harbor Fest Celebrates Milwaukee’s Waterways
Sep 25th, 2025 by Michael Holloway
-
Bay View Bash Takes Over KK
Sep 18th, 2025 by Michael Holloway
-
Ren Faire Returns To Riverwest
Sep 11th, 2025 by Michael Holloway