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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. Door County Century

  • Date: Second Sunday in September
  • Style: Road ride
  • Established: 1979
  • Support: Six rest areas
  • Cost: $65-$80

Door County is famous for its scenic beauty and it should be fairly clear why a bike ride around the peninsula is a must-see.

The ride offers varying distances from 30-100 miles that takes you around the peninsula, through apple and cherry orchards. Much of the route sticks close to the water and there are many support stations along the way.

The ride ends with a catered dinner, beverages (hydrating and otherwise) and live music.

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