Our Challenge to You

Complete all 10 sections, 1,200 miles
(we have 3 ways to do it)

Don’t Be Fooled,
This Takes A Lot Of Hard Work

Most people in the world won’t ride 1,200 miles in their lifetime.
This is no small task, we recommend you take it seriously and train hard so you can enjoy the time while your riding.

10 Day Challenge

Complete TDY in 10 days straight.
That’s right, ride all 10 sections in 10 consecutive days (1,200 miles).

Riders that sign up for our 10 day challenge get a FREE Plaid Finisher’s Jersey upon completion.
The jersey is only free for those that ride all 10 sections in 10 straight days with the event in August.
Plaid Jersey will be handed out after the 9th day of riding is complete, so you can wear it with pride on the 10th day.

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

Learn More

Chasing Plaid Challenge

This challenge is a little more relaxing, complete TDY in 10 days, even if it takes 10 years to do it.
(You must ride an entire section in 1 day).

We offer 2 and 3 day ride packages every year to help you complete the sections you still need to ride in order to close the loop.

When you’re going to be riding your 10th section, be sure to order your Plaid Finisher’s Jersey when you register,
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

Copper Ride Challenge

Complete each section in any number of days you want.   That means you can take any number of days you want to complete one section,
ride any number of miles you want each day
and ride them in any order you want.

This challenge is much more relaxing and a fabulous way to enjoy the serenity of the UP, stop in the cute towns and stop any time you want to.

Your goal is to ultimately ride all 10 sections.

We want you to get outside, push your limits and see the beauty of the U.P.

You can ride with the group in August or join our Club Membership program and ride on your own.

If you ride with the group and don’t complete the entire section, depending on the time,
you may have to provide your own transportation to the next city.

Once you complete all 10 sections you will be eligible to purchase a TDY Copper Finisher’s Jersey
(sorry, Plaid is for those who do each section in 1 day).
Our Copper Jersey is sure to stand out and please everyone, especially you when you wear it with pride.

TDY Official Ride

TDY’s group ride will be held 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 Rides

Can’t Ride in August, See If This Works For You

We realize not everyone can ride in August, for that reason, we are now offering a Club Membership for riders to still be a part of TDY.

Learn More

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.

Plaid Finisher’s Jersey

All riders who sign up for the 10 Day Challenge Ride and complete all 10 sections,
will receive the Plaid Finisher’s Jersey as a REWARD for completing all 10 sections in 10 straight days.

Riders will receive their Plaid Finisher’s Jersey after they have completed 9 sections
(we assume once you’ve done 9 sections, the 10th will be a easy).

The Plaid jerseys will be handed out the night before we ride the 10th section.

Women’s Plaid Finishers Jersey
Men’s Plaid Finishers Jersey


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.