Our Challenge to All Riders Is Simple

Complete all 10 sections (1,200 miles), no matter how long it takes you.
It is a great accomplishment!!

TDY’s Ultimate Challenge is our 10 Day Ride

Complete TDY in 10 straight days.

It is no small task, ride 1,200 miles in 10 days, through sunshine and rain, cold weather and hot, it’s Michigan, expect it all.

Free Plaid Finisher’s Jersey

That’s right, ride all 10 sections in 10 consecutive days and get a FREE Plaid Finisher’s Jersey.
Must register before June 1st and ride with the group in August to be eligible for the FREE Plaid Jersey.

Plaid Jersey will be handed out after you have completed your 9th day of riding, so you can wear it with pride on the 10th day.

This is our toughest challenge, are you up for it?

Learn More About Our Ride Options

Chasing Plaid Challenge

This challenge is a little more relaxing, complete all 10 sections of TDY, even if it takes 10 years to do it.
(You must ride an entire section in 1 day, you can’t complete 1 section in 3 days).

We offer 2 and 3 day ride packages every year to help you close the loop.

Most riders know when they know they will be riding their 10th section, when that time is for you, be sure to order your Plaid Finisher’s Jersey when you register, so you can wear it with pride on your 10th section.  Plaid jerseys will be handed out after you have completed your 9th section, so you can wear it with pride on your 10th section.

Our 2 and 3 day rides are perfect for completing a few sections each year.

Learn More About Our Ride Options

When We Ride

August 6 – 15, 2021

We highly encourage you to ride with the group, meet a ton of fabulous people and enjoy the adventure of a lifetime.

Learn More About Our Ride Options

Is TDY Tough?

Depends on how many days you ride. If you’re riding 1 day and you train early enough, you’ll be fine.

But if you’re riding all 10 days…make no mistake about it, this is a TOUGH RIDE.  Both physically and mentally.

Some sections riding 1 day is like riding 3 other sections at once.

We ride through rain and shine, some days sun up until sun down.

Like everything else in life, preparation is the key.  Train early and train hard and you’ll be able to fully enjoy TDY and all the UP has to offer.

See our Training Tips tab above for assistance.

Don’t Be Fooled, It Takes Hard Work To Ride Any Section

Most people in the world won’t ride 1,200 miles in their lifetime, let alone in 10 days or over the course of 10 years.

Riding 6 to 8 to 10 hours a day is no small task, we recommend you take it seriously and train hard so you can enjoy the time while your riding.


There is a $50 processing fee for all refunds given.
No refunds will be given after March 1, 2021.
No partial refunds for sections that riders did not finish
No exchanges on any jerseys.