2018 Milwaukee Bike Ride Guide

Get out your favorite biking shorts, (or tweed) because Milwaukee has plenty of bike rides this summer.

Milwaukee Underwear Bike Ride

Yup, you read the name right. The kickoff for this five-part bike ride begins June 15 from 7 p.m. to 10 p.m. (top of Reservoir Hill) with an after party at Company Brewing (735 E. Center St.) from 10 p.m. to 2:30 a.m. The ride celebrates fun and positive self-body image and this summer, riders are encouraged to bring clothing items to donate to Pathfinders.

MKE Tuesday Night Rides

If you’d like a more consistent group, meet up with MKE Tuesday Night Rides (MKETNR) to go on a ride for bicyclists of all levels. The group meets up throughout spring to fall every Tuesday (rain or shine) at Purple Door Ice Cream (205 S. 2 St.) at 6:30 p.m. for a 30 to 90 minute ride around various Milwaukee neighborhoods. Come to bike and make friends along the way.

Sistas & Mistas CoEd Bike Ride

Join Black Girls Do Bike MKE as they bike a CoEd ride with women and their supportive other half on June 16. The ride begins at Hart Park (7300 Chestnut St.) at 9:45 a.m. with wheels down at 10 a.m. This chill ride will be paced a little slower as the group rides through the Oak Leaf Trail and other parks. Feel free to stay after for food and fellowship.

Fat Tire Tour; photo courtesy of Jason and Amanda Manders

Fat Tire Tour of Milwaukee

The Fat Tire Tour of Milwaukee is the oldest group ride in the greater Milwaukee area. As for the route, it remains a secret until the morning of, so get ready to explore new parts of Milwaukee. This year, the movie-themed group ride theme is ‘Young Milwaukeestein.’ The ride takes place June 16 from 9 a.m to 6 p.m. and meets at Best Place at the Historic Pabst Brewery (901 W. Juneau Ave.).

Ciclovia MKE

The annual Ciclovia is returning to Milwaukee for the fourth summer on June 17 from noon to 3 p.m. This free public event celebrates open streets and healthy lifestyles for all. The ride starts on Chavez Dr. and National Ave. for about 1.16 miles.

Ciclovía MKE; photo by Elizabeth Cruz

Adventure Bike Day Camp

This one is for all the kids who love to bike but sick of their same old places. The Adventure Bike Day Camp runs from June 18 through June 22 run by the Wisconsin Bike Fed’s staff (3618 West Pierce St.). During the camp, kids ages 10-13 can ride with staff through the Menomonee River Parkway, Three Bridges Park, Mitchell Park Domes and the Oak Leaf Trail.

Polish Moon Ride 

Celebrate your heritage, or just come out for fun to the Polish Moon Ride on June 22 with the ride starting at 7 p.m. at Fuel Cafe and Nomad National Fanzone (630 S. 5th St). The slow-paced 8-mile ride winds around historic Polish neighborhoods through the “Streets of Old Milwaukee.”

Riverwest 24

Grab some friends or try the challenge solo for the annual Riverwest 24 Hour Bike Ride from June 27 to June 28 in various Riverwest neighborhoods. Although the ride may seem daunting at first, the ride is meant to celebrate the neighborhood, encourage Milwaukee cycling and have fun with friends.

2013 Riverwest24; photo by Sara Stathas

Milwaukee Tour de Cure

The American Diabetes Association once again sponsors the Milwaukee Tour de Cure, a national bike ride to fight diabetes together. All bikers, runners and walkers are welcome to participate in the event on July 14 at Hoyt Park (1800N Swan Blvd.) with check-in times ranging from 7 a.m. to 10 a.m. depending on the length of the race.

Coffee Bean Classic; photo by Gary Smits

Colectivo Coffee Bean Classic

If you would like more of a challenging but fun ride, check out the annual Colectivo Coffee Bean Classic on July 22 at Minooka Park (1927 E. Sunset Dr.). There are various distance options, but once you’ve finished the ride, Colectivo will be pouring free cups of their classic brew: hot or cold.

Wisconsin Women Century Ride

The 4ht Annual Wisconsin Women Century Ride offers various distances for female cyclists of all levels. The ride is for females only and takes place throughout roads of the Northern Kettle Moraine and takes place on July 28 from around 6 a.m. to 2 p.m.

Bike MS: TOYOTA Best Dam Bike Tour

This ride is for the more bike-savvy. Thhe Bike MS: TOYOTA Best Dam Bike Tour is a two-day cycling ride that takes participants from Milwaukee (Waukesha County Technical College – 327 E. Broadway St.) to Madison, with a night in between at Whitewater from August 4 through August 5. Even better, the race supports research and services to live in a world without MS.

Ride Across Wisconsin

The name of this bike ride is pretty self-explanatory. The Ride Across Wisconsin bike ride takes place August 11 and begins in Dubuque and takes participants along scenic routes across the bottom of the state. The ride totals about 175 or 105 miles, but there are rest stops every 25 miles and food stops along the way.

Project Echelon Omnium

Is your fitness level ready for the test? Challenge yourself with the Project Echelon Omnium, a free ride to support Veterans. The ride is two days from August 11 to 12 with three stages and challenging courses including a hill time trial, two technical circuit races and a 6 mile time trial.

Hitting 4 the Cycle

The 4th Annual Hitting 4 the Cycle bike ride at Miller Park will take place August 25 starting at 1 p.m. A Brewers Community Foundation fundraiser, the ride raises money for programming to support children and families in Wisconsin. After participants ride around Milwaukee and Lake Michigan, all are welcome to stay for a tailgate party and even buy tickets to watch the Brewers vs. the Pirates later.

2nd annual “Hitting 4 the Cycle” ride Saturday August 13th, 2016. Photo by Scott Paulus/Brewers

Milwaukee Historic Brewery Bike Tour

The athletic yet fun and interesting bike ride takes participants to historic brewery sites of Milwaukee. The Milwaukee Historic Brewery Bike Tour takes place every Friday and Saturday at various times. They are even revamping their tours, so if you’ve done it already, you may as well try out what else they’ve got up their sleeves.

Milwaukee Tweed Ride

Hate the typical biking outfits? Break out your favorite tweed outfit for the annual Milwaukee Tweed Ride in mid-October. Have some fun, dress up and even stop for a beer or two afterwards.




Caroline Blair is a digital marketing intern for Milwaukee Magazine. She just finished her sophomore year at Syracuse University studying magazine journalism and marketing. She grew up in Milwaukee and is excited to be spending her summer here interning at Milwaukee Magazine.