September 29, 2026
September 29, 2026

Ride Classifications and Difficulty Levels

By Glenn Schneider
What to expect for beginning, intermediate, advanced rides and some tips on how to get ready for any distanced overnight

We welcome all types of cyclists on our rides, but it is helpful to know whether a ride might be inside your comfort zone or whether it might push you a bit farther than your previous experiences. We're big fans of taking things at the pace that works for you just as much as we're a fan of hitting new milestones and Type 2 fun. So we've created this guide to help folks understand our ride types. If you have any questions about a ride, please don't hesitate to reach out to us at info@oofd.org. 

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OOFD Ride Types:

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Beginner Friendly: Mostly paved trails, water/rest breaks every 10-15 miles. Average 12-15mph on Adult rides (a casual, conversational pace). 7-10mph on Family and Adaptive rides.

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Intermediate: Mixed terrain: pavement, crushed limestone, and gravel. Water/rest breaks every 15-20 miles. 12-15mph on Adult rides (a casual, conversational pace). For Family and Adaptive rides, an intermediate classification signals more mileage at the higher (~10mph) pace. 

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Advanced: Mixed terrain: pavement, crushed limestone, gravel, possible singletrack (a narrow dirt trail). Water/rest breaks every 15-25 miles. Average 13-15mph (a conversational pace), with some sections possibly 16-18mph (short convos, focus on your breath). 

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When classifying rides, we take into account these factors:

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Surface Type

The majority of our rides are on pavement, and some have sections of crushed limestone. Crushed limestone (also called "poor man's asphalt”) is pretty darn smooth (click the link to see and hear a bike on a local crushed limestone trail). Note that if it's a wet day, you'll work a bit harder on crushed limestone. 

  • A few rides that explore the Des Plaines River Trail or I&M Canal Trail will have sections of gravel (click these links to take a peek!). If you're on thin tires (23-28mm), you might fishtail a time or two if there is looser gravel, but balance is your friend. Some of our guides ride on thin tires, too. If encountering gravel, just slow down, maintain some distance between you and other riders, and keep those elbows bent :)

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Frequency of Rest Stops

Across our Adult rides, we stop every ~15 miles for water and bathroom breaks. We also plan an extended lunch break (typically one hour). On high-heat days and on Family and Adaptive rides, we take more short rest stops. If you need a break before a planned stop, let a guide know and they'll be happy to stop with you.

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Distance

‍We welcome and encourage riders to join us on rides that are longer than they've ever ridden. We can't wait to celebrate that milestone with you! Having said that, we recommend some level of experience for the best chance of a fun adventure:

  • For a 30-40 mile ride, ideally you've ridden 20-25 miles before
  • For a 50-60 mile ride, ideally you've ridden 35-40 miles before
  • For a 70-80 mile ride, ideally you've ridden at least 45-55 miles before

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Pace

Each ride has a planned pace, with Family rides in the 7-10mph pace, and Adult rides averaging a 12-15mph pace. Longer distance Adult rides (such as our 100-milers Waterways to the West and Train O’ Lakes) may extend sections of the ride to an average of 16-18mph so we can make it to camp before sunset. 

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Not quite sure what these speeds feel like? Here's a handy way of thinking about it in terms of distance…

  • 20 miles at 10mph = 2 hours
  • 20 miles at 12mph = 1 hour 40 minutes
  • 20 miles at 14mph = 1 hour 25 minutes
  • 20 miles at 16mph = 1 hour 15 minutes
  • 20 miles at 18mph = 1 hour 5 minutes

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Across all rides, it's not uncommon for the group to split into a slightly faster group and slightly slower group. Rest assured that there will be a guide leading the way and additional guides in each group so everyone gets where they need to go and support is there if you need it.

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What Our Riders Have Said About Pace and Distance

We always poll our riders about their experience after an adventure, and here is some feedback we’ve gotten to the question, “How did you feel about the total mileage of the ride?”

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“Great early season opener - just enough to challenge the legs and build confidence for the longer rides ahead.”

  • Andy J on What Lies West

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“The first day was the longest I've ridden in one day. I was nervous about it, but it went great! I was also happy I shortened the second day by taking the train back.”

  • Rob U on Battle to the Dunes

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“Mileage was in the goldilocks zone.”

  • Jason T on Battle to the Dunes

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“Was challenging but I appreciated it. I would never ride that far on my own.”

  • Mary G on SWMI

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“Very nice. The break points and spots felt just right. I think the changes in geography and rural vs non-rural of this ride make it seem like riding a number of shorter, distinct segments.”

  • Clarence B on Drumlins of WisKohler

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Glenn Schneider
()
OOFD Co-Founder, Executive Director and Guide
Glenn likes peanut butter and jelly sandwiches, plus he's a traveling fool. You can catch him riding the trails around the Basin on his trusty steed.

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