2017 Milwaukee Bike Ride Guide

Whether you’re an amateur or pro cyclist, here is your guide to Milwaukee’s best cycling rides this year.

UPAF Ride for the Arts
June 4

With rides from 5 to 70 miles, there’s a route for everyone at UPAF Ride for the Arts, the Nation’s largest one-day recreational bike ride that raises money for the performing arts. Riders will also have the chance to cycle over Milwaukee’s Hoan Bridge.

Photo courtesy of the United Performing Arts Fund.

Wisconsin Bike Week
June 1-10

With events throughout Wisconsin, it’s nearly impossible not to get involved in this year’s Wisconsin Bike Week. Events range from family fun rides to an opportunity to bike with Milwaukee Mayor Tom Barrett. There’s a biking event for everyone.

Ciclovia MKE
June 11

Ciclovia MKE returns to Milwaukee for its third summer this year. Whether you walk, dance or bike, take to the streets! Free to the public, Ciclovia’s open streets initiative encourages healthy lifestyles throughout Milwaukee’s diverse neighborhoods. This year’s route spans from Cesar E. Chavez Drive to Layton Boulevard via National and Greenfield Avenues.

Photo courtesy of Ciclovia MKE.

Underwear Bike Ride
June 15

The first Milwaukee Underwear Bike Ride of the summer is taking place on June 15. All those planning on participating will meet at the top of Reservoir Hill at 7 p.m. and the bike ride will begin promptly at 8 p.m. The Underwear Bike Ride is a monthly ride and further dates are yet to be determined. 

Polish Moon Ride
July 1

Honor your German and Polish heritage and take part in the fourth annual Polish Moon Ride. This slow, eight-mile cycle is police-led and perfect for the whole family. The night begins with the playing of the National Anthem and ends with an after-party filled with delicious Polish and Mexican food and a polka band. Don’t forget to bring your dancing shoes!

Milwaukee Tour de Cure
July 22

This fundraising cycling event takes riders on one of five scenic routes that range from 5 to 70 miles long. Raise awareness and money for the American Diabetes Association and reward yourself with a cold brew and giant pretzel after cycling.

Colectivo Coffee Bean Classic
July 23

Riders hit some of the latest and greatest cross-country mountain bike trails in the Midwest at the Minooka Park trails during the Colectivo Coffee Bean Classic. If mountain biking isn’t your thing though, grab a cup of freshly brewed Colectivo coffee at the coffee bar and head to the sidelines to cheer on the racers from the Colectivo Coffee Mountain Bike team.

Riverwest 24
July 28-29

24 hours straight of cycling, volunteering and spectating begins July 28 at 7 p.m. Milwaukee’s Riverwest community comes together to welcome new people and strengthen relationships at an event that promotes biking in an urban environment. So roll out your bike or break out your lawn chairs and settle in for full day cycle.

Bike MS: TOYOTA Best Dam Bike Tour
August 5-6

This two-day bike tour takes riders from the Milwaukee area to Madison with an overnight pit-stop in Whitewater. With numerous routes to choose from each day, each rider will get experience Wisconsin’s varying terrain. Proceeds from the race go to MS research.

Best Dam Bike Tour. Photo courtesy of Nichole Shaffer.

Hitting 4 the Cycle
August 12

This 25 mile route starts and ends at Miller Park and benefits both local non-profits and the Brewers Community Foundation. After the ride, participants can enjoy a fun-filled tailgate party and then head to the Brewers versus Reds game later in the evening.

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

Milwaukee Historic Brewery Bike Tour
Second Saturday of the month, May-October

Bikes and brews! This bike tour takes riders to some of Milwaukee’s most historic brewing sites. While it’s not a pub-crawl by any means, the tour does stop at the Milwaukee Ale House for lunch where you can sneak a cold one, and it ends at Lakefront Brewery for their famous tour.

MKE Tuesday Night Rides
May 30-October 3 

Enjoy a night out on the town with MKE TNR. Each Tuesday, riders meet to bike and enjoy food or drink from a local Milwaukee restaurant. Food, friends and a nice cycle, trip. What more could you ask for?

Milwaukee Tweed Ride
October 14

Say goodbye to spandex and break out your best tweed suit for this parade-like cycle trip. This years Tweed Ride will pass through Bay View and keep onlookers wondering whether or not they’ve been taken back in time.

Tweed Ride 2016 photo courtesy of Mike Spanjar.




Megan Otto is a digital and editorial intern at Milwaukee Magazine. She currently attends the University of Wisconsin-Madison and has previously interned in London.