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The Dairy-Roubaix kicks off the season's must-do rides around Wisconsin. (PHOTO: Jason McDowell)

The 10 best bike rides in Wisconsin

Note: The contents of this guide were checked for accuracy when this article was updated on May 2, 2019 at 9:01 a.m. We continually update the thousands of articles on OnMilwaukee.com, but it's possible some details, specials and offers may have changed. As always, we recommend you call first if you have specific questions for the businesses mentioned in the guide.

There are a lot (and I mean A LOT) of great rides around Wisconsin, and it's hard to narrow them down to just 10. The good news is, this list is not the end-all, be-all of rides around the state, and we've included great jumping off points for each ride for even more exploration.

From racing to fundraising to slow rolls, here are the ten best rides in Wisconsin, organized chronologically by the time of year in which they appear.

And by the way, if you're tentative about racing, don't worry. These events have been selected for their ease of entry; while basic bike handling skills are necessary and competition is spirited, there is no minimum speed required.


10. Dairy-Roubaix

  • When: Mid-April
  • Style: Gravel/All-road
  • Established: 2011
  • Support: One rest stop 25 miles in. There are sanctioned drop zones for your own water and supplies after the 54 mile split.
  • Cost: Free, but donations to Vernon Trails are accepted.

Dairy-Roubaix (Dare-ee Roo-bay), which rolls out of Wyalusing State Park near Prairie du Chien, is a challenging gravel ride up and down the picturesque bluffs of the Mississippi River Valley. Riders can choose between a 54-mile and a 106-mile route, but when it comes to this ride, thanks to the 4,000-8,000 feet of climbing, elevation counts as much as distance. Half of the route is gravel, and the hills are punchy and challenging to all but the fittest.

Scheduled around mid-April, it's a great way to kick off the spring season, and while weather can rock back and forth between most ideal and less optimal, the ride has, thus far, had a decent winning streak in terms of sun and warmth.


9. Milwaukee Messenger Invitational (MMI)

  • When: Mid-April
  • Style: Open street race with scavenger hunt
  • Established: 2001
  • Support: None
  • Cost: $5-$10
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The invitation is extended to all who are interested in role-playing as a letter carrier and typically draws folks from Chicago, Madison and Minneapolis, making it Milwaukee's biggest and most enduring messenger race. The format changes every year, so it's hard to predict how to win, but these races tend to be less about speed (though it helps) and more about scavenger hunts, various puzzle-solving skills and, most importantly, knowledgeable routing.

The event is run by bike messengers and is thus unsanctioned and on open city streets, so expect to keep your wits about you if you plan on competing. If throwing yourself to the motorized wolves is not your bag, organizers are always happy to have more participants, so you can always ride for fun. Just remember to bring a backpack, a lock, positive vibes and a pen. (Oh, god, don't forget your pen.)


8. Miller Lite United Performing Arts Fund (UPAF) Ride

  • When: First Sunday in June
  • Style: Road ride
  • Established: 1967
  • Support: Depending on the distance, there are up to four rest stations along the way, as well as a party at the end.
  • Cost: $50-$60, but it's a fundraising ride, so you may want to consider donating more.

The biggest and oldest bike ride in Wisconsin is also the primary funding event for the United Performing Arts Fund. Riders can choose from routes in various distances from 5 to 65 miles, up to Port Washington and back.

The UPAF ride achieved must-do status thanks to its history as one of the oldest rides in the state, its massive participation and recent addition of the Hoan Bridge. This is the only time you'll be able to take non-motorized apparatuses up the bridge (at least until they re-deck it in 40 years).

After crossing the Hoan, the route takes riders down lakeside roads and between budding farm fields before looping back to the finishing party at the Summerfest grounds.


7. MKEBKE Underwear Ride

  • Date: Once a month from June to September
  • Style: Slow roll
  • Established: 2009
  • Support: There is sometimes volunteer support at each stopping point, but it's never guaranteed, especially en route. Ensure your tires are properly inflated so you don't get stranded, and maybe bring a bus pass, just in case. BYOB.
  • Cost: Free

Doff your shirt and pants for this slow roll, which encourages body positivity to fight ageism and sexism (and all the other bad -isms and phobias). Each ride starts and ends at various spots and plots unique courses through the city, at distances between 8-10 miles out (and then back).

The ride kicks off shortly before sunset. The pace is very casual, spirits are high and the ride usually ends with an underwear dance party scored with live music.

For success, make sure you bring a front and rear light, pump up your tires to prevent flats and lock up when you reach each stop.


6. Riverwest 24

  • Date: Last Friday & Saturday in July
  • Style: Open street race with scavenger hunt
  • Established: 2007
  • Support: Self-supported, but you're always in the neighborhood
  • Cost: $24

This started as a community event with less than 200 people – most of whom signed up the day of the race – to a thousand-person extravaganza that sells out in a few hours and has since earned the nickname "The People's Holiday." Through its history, it has maintained its DIY, punk-rock attitude by refusing sponsor dollars and relying on neighborhood volunteers get it organized.

The course is a four(ish)-mile loop through the Riverwest neighborhood, which requires riders to stop and punch a manifest at every corner. The goal is to ride the most laps in 24 hours and complete each bonus checkpoint that opens along the way including the opportunity to commemorate the year with an annual tattoo. You can participate as a sleepless solo rider, a tireless tandem team or as a relay team to ensure some shut-eye.

Sign-up is now on a lottery system and you must be present to win, but if you want to cheat the line, lend your hand as a volunteer and get a free entry to the race the following year.

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