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Milwaukee bike events, from casual rides to exhilarating races

Bike events around Milwaukee include (clockwise from top) the Riverwest 24, Tour of America's Dairyland, Santa Cycle Rampage and UPAF Ride for the Arts.
Riverwest 24 / Tour of America's Dairyland / Wisconsin Bike Fed / UPAF
Bike events around Milwaukee include (clockwise from top) the Riverwest 24, Tour of America's Dairyland, Santa Cycle Rampage and UPAF Ride for the Arts.

It seems we’ve got bikes on the brain within the walls of Radio Milwaukee. Last week, it was our favorite places to ride around Milwaukee on any ol’ day. Today, we get more time-specific with a selection of cycling events happening during this last month of spring and throughout the summer (plus one holly-jolly ride for good measure).

The bonus to the list you’ll find below is the communal aspect. A solo ride on your go-to route can be food for the soul and cleanser for the stress that builds up from day-to-day. But it’s also important to connect with other people now and again, especially around something you all enjoy anyway.

So take a look at all of the opportunities you have to make those connections in the weeks and months ahead, mark your calendar for the ones that jump out, and maybe even register right away for the ones that REALLY jump out. You can also go well beyond these suggestions and use the Wisconsin Bike Fed’s customizable event calendar to find other things happening all over the state.

One more reminder: You could do at least some of these events from the seat of a brand-new bike we’re giving away at the end of this month, courtesy of our friends at Fyxation. All you need to do for a chance to win is make a donation of any amount to Radio Milwaukee between now and May 31. For more information and photos of the very handsome bicycle you could win, head over to our membership page.

June 2: UPAF Ride for the Arts

More than just a ride, the United Performing Arts Fund’s annual cycling event is an opportunity for friends, families and coworkers to have fun and support our region’s world-class performing arts organizations. Bike the Hoan and support the arts on the 20-mile Hoan Loop Course where bikes rule the road!

June 4: Milwaukee Tuesday Night Rides

Join the Bike Fed for a special Wisconsin Bike Week edition of Milwaukee’s longest running weekly slow roll. The ride averages a casual 10 mph with a travel distance of between 2 and 12 miles total, plus a mid-ride break. This year’s Bike Week ride will focus on locations that have joined Bicycle Benefits, the nationwide program in which businesses provide discounts and special offers to patrons who choose to visit by bike.

June 13-23: Tour of America's Dairyland

Tour of America's Dairyland presented by Wisconsin Milk Marketing Board is the largest competitive bicycle racing event in the United States. At the various stops — from Shorewood to Cedarburg and Tosa to West Allis — you can cheer on pro-am athletes from more than 40 states and 15 countries. Altogether, it's 11 days of family-friendly fun featuring races, kids' activities, food, drink, music and more.

June 15: Fat Tire Tour of Milwaukee

Drawing nearly 500 attendees each year and with nearly 40 years under its tires, the Fat Tire Tour of Milwaukee is the oldest and most historic group ride in the greater Milwaukee area. This casual-paced event covers 15-25 miles over a 6-7 hour span and is movie-themed, with this year’s honor going to Pee Wee’s Big Adventure. Dress up (or don’t), ride along and have a good ol’ time.

June 23: Colectivo Coffee Beans Classic

This one’s for the mountain bikers. Part of the Wisconsin Off-Road Series, the Colectivo Coffee Bean Classic is a chance for riders to race through Waukesha’s Minooka Park on a route tailored to their age and skill level. Known for its tight and twisty track, the park contains one of the most popular mountain bike trail systems in the region, and the event of course features Colectivo coffee to keep you energized throughout.

July 26-27: Riverwest 24

As much block party as bike event, the RW24 was born through block watches throughout Riverwest and is an annual reason to come together for a stronger Milwaukee. It’s an incredible test of stamina and teamwork for the riders. For the spectators? Not so much. But everyone takes away a feeling of joy and togetherness that keeps people coming back year after year.

Aug. 17-18: Ride Across Wisconsin

The Bike Fed’s largest fundraiser of the year will revisit its route from La Crosse to Milwaukee one last time with options to ride entirely on paved surfaces or on a combination of crushed limestone trail and low-stress roads. This year’s route showcases the Elroy-Sparta State Trail Tunnels, Wisconsin Dells, Merrimac Ferry, Trek’s World Headquarters and a new finish line at City Lights Brewing Company. With one- and two-day options, riders can choose a 235-, 165-, 135- or 100-mile challenge based on their abilities and ambitions.

Sept. 8: Ride on the Wild Side

Bikes at the Milwaukee County Zoo are a no-no 364 days of the year. Then there’s this day — the one time you can pedal through the zoo past curious caribou and indifferent prairie dogs. Electric- and person-powered bikes are welcome as you navigate the 2.5-mile kids ride or take on the challenges of a 10-, 17- or 27-mile route.

Dec. 7: Santa Cycle Rampage

Undoubtedly the coldest event in this list, the Bike Fed’s Santa Cycle Rampage is arguably the most merry. Hundreds if not thousands of Kris Kringles roll through Milwaukee with police escorts, all to raise funds for youth- and family-based education and encouragement programs in Milwaukee County. There’s a 12-mile slow roll, and in 2023 the event added a 3-mile “Elf Cycle Frenzy” for the littlest riders.