I Tried To Ford The River But My Oxen Died

I should have caulked and floated it across, but it was way more fun to watch the wagon break apart for some reason. Who else geeked out playing Oregon Trail back in the day? I recently found that you can play it free on this site – quite entertaining during quarantine. Fast forward to this week when my friend Terri asked if I wanted to join her in an Oregon Trail Challenge by teaming up to complete the 2,000 mile journey via running, walking, biking and other activities. We actually visited the End of the Oregon Trail together a few years ago, so this will be a fun way to stay focused on our fitness goals as we meet the challenge checkpoints along the way.

What’s This Challenge All About?

You have the option to join up to 5 friends on a team to complete 2000 miles together, complete the 2000 miles yourself, or you can choose the mini solo option to complete 200 miles yourself.

How does the challenge work?

Run, walk, bike, skate, kayak, skip, row, spin, swim, or some other kind of activity the entire distance of the Oregon Trail. (2,000 Miles for the Solo or Team Wagons, or 200 miles for the Mini Wagon)

How does the “mini challenge” work vs the regular challenge?

The mini wagon challenge is 200 miles instead of 2,000 miles. So every mile you do in the mini challenge moves you 10 miles on the Oregon Trail. 

That means you only have to do 31.7 miles in the mini challenge to get to checkpoint #1 (Fort Kearny) vs the regular challenge participants who need to log 317 miles. See more about checkpoints below.

How do I keep track of my mileage?

You will track your miles on the website (goes by the honor system), but ideally you use a GPS watch or phone to track your workouts.  My Vivoactive keeps a record of my miles each day, so that’s how I will be keeping track of my miles.

What’s The Timeframe?

You must complete your miles by 5/15/21, so the sooner you register (and the more friends you can recruit to join your wagon), the more time you’ll have to complete your miles! Right now we have 3 in our wagon, so let me know if you’d like to join our team and I’ll give you the Team Wagon details! If we fill our wagon, we will need to average 12 miles per person each week – totally doable!

I’m Not A Runner – Can I Still Do This?

YES! I’m not running much right now, so most of my miles will be from walking and hiking, but as I mentioned above, you can also bike, skate, kayak, skip, row, spin, swim, or any other type of activity you love to get your miles in!


You/your team will receive Digital Checkpoint Badges (when you reach your checkpoints) and a commemorative Medal & Patch (7-14 days after the completion of your challenge).

I’m a sucker for fun t-shirts, so of course I had to get the dysentery one. It’s an extra $20 to get a t-shirt, but well-worth it to document this adventure, if you ask me!

best damn race oregon trail

Ready To Register?

You can do 2000 miles split between up to six friends, 2000 miles on your own, or lead a “solo mini wagon” for 200 miles. Go here to get signed up and get your own snazzy bib like mine below! Let’s knock out some fitness goals as we finish up this year and start 2021 on the right foot!


  1. Writer Rinker Buck wrote a book called “The Oregon Trail” several years ago..he and his brother navigated the entire original route by horse-drawn wagon! True! It’s interesting to see how much of it still remains, and the fascinating social and geographical changes to the county as well…

    Liked by 2 people

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