How A Roadie Met The Oregon Trail

It’s funny that all of these gravel races that I’ve been doing started because of the road, and lack thereof. The game is always changing.

It probably dates back even further to when one of my mentors, Mike Minerva, said, “So, when are you going to stop doing the little local races and just do the big ones?”

Wait, what? 

Why would I do that? Racing is so freaking fun, and it keeps me focused and hungry; for fitness and for life. Why would I only do the big ones?

As a category 1 racer, there are only a handful of races that you can actually do at the Pro level, and sometimes you need a full team to be able to get into those prestigious road races, so why do just these few big ones?

What about guest riding though? Hmm, that is an option, but riding as a guest rider never seemed like something I’d want to do, because you’re just slotted in with some random people for the sake of having a roster to race, but I probably should have put more effort in and tried that. 

I also should have tried to make more friends within the racing scene. Being on a small team, and often traveling alone, I let shyness and a sense of fear get in the way of simply walking up to a group of people and saying, “Hey, how’s it going?”

I could blame the roadie culture that can be clique-ish, but I like to take responsibility so I blame myself for not being more extroverted at the races, and it’s something I’ve been working on (hey new friends from Oregon!!).

I’ve made sure to use that simple tactic more and more in my life today. Try it: “Hey, how’s it going?” It’s the easier ice-breaker and open ended question. Let me know if you try it.

Lots of Miles >>> Lots of Circles

If you’re just getting to know me, big crits aren’t my thing; those aren’t the big races I’m referring to. I’ve never found them fun (read: scary) and it was never naturally appealing to me; drive 5 hours to the big crit and race 70-90 minutes? Pass. Some call it the sideshow of real racing, which as mentioned above, doesn’t really exist here since road racing is somewhat dying; well, the current format is.

Insert mass start road racing, gran fondos, and, well, gravel?

As someone that loves big miles over going really fast, road races are clearly what I’m searching for, and always have been. 

I see what Minerva meant now: the mental energy, travel, cost, and everything that goes into getting to the big races can get pushed to the side when you’re racing small local or regional ones every damn weekend. The smaller weekends still take a toll on mental energy, family time, and getting things done at home on the weekend. When many of those accumulate on each other, the thought of a massive big week or weekend just seems like way too much.

Why not skip all these smaller weekends and just try to get into the big events.

No big road events: INSERT GRAVEL.

Photo by Andy Chasteen

Photo by Andy Chasteen

Try New Things

So fast forward to the middle of 2018.

“Hey, we’re starting a gravel squad; you interested? They’re basically road races without coasting, and you might be good at the non-technical courses. Plus, pro’s are starting to do them.”

I almost think they knew that’s what would hook me. I JONES HARD FOR PRO ROAD RACES. It’s always been a disappointment that there are only 1 or 2 a year that we can do as amateurs, and I missed the boat this year at JMSR when we finally found out we were doing the PRO race and not the Cat 1 / 2 race; I was deep in a hole for my 350 mile gravel attempt at Iowa Wind and Rock.

Pros, at gravel races? A new genre, new rules, new everything? I like it.

I already wrote a blog about the 2018 Gravel Worlds, (my new website is a mess so ignore the rest of it for now, thaaaaanks) but the takeaway from there is that we were giddy with excitement and nervousness the night before. We really had no idea what we were getting ourselves into and it was thrilling:

The night before we were so EXCITED to wake up at 3:45am for a 6am race. I was more excited than I've been in a while for any road race that I did that wasn't a pro race (none this season). I see different things on our horizon; big road only, big gravel, less mini races, more big adventures. The game is changing, and we need to stay nimble.

The game is certainly changing, and I’ve embraced what Minerva said: go after the big stuff. I just didn’t realize at the time it wouldn’t be solely on the road.

2019: Bigger Races

Last year was disappointing as many times we’d show up to a usual big race in Tennessee, only to find out that there were 5-12 guys racing in the P/1/2 race. That’s hardly a race, and it sure doesn’t feel amazing when you win.

Master’s races (I’m now 37) had bigger fields and littered with amazing athletes; former pros, masters world champions, guys who ride bikes a lot. Maybe I should do Masters instead? But Patrick is only 32 so we wouldn’t be racing together.


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In a quest to do only big events, I decided gravel was the route. The spring campaign looked like this (gravel in bold):

Land Run 100 - Gravel in Oklahoma

Oak Ridge Road Omnium - skipped, as there were 12 racers

Shrevesport Crit - cancelled

Joe Martin Road

Gravel Nationals

Iowa Wind and Rock

Dirty Kanza - did not get in from lottery

High Roller Crit - cancelled

Tulsa Tough - roster filled for P/1 (thank goodness) and didn’t reg in time for ½

Cherohala Challenge - went and did a 2 hour climb and it was amazing, even in full rain

Oregon Trail Gravel Grinder

Clearly, the biggest events were the gravel ones, where I learned a ton, became a better cyclist, and had a blast doing it! 

No gravel wins, only 1 podium (technically the age group winner at Gravel Nats but raced the Open category so the result wasn’t counted), but a better me. Oddly, still feeling as much a winner as I had when I was winning more often. 

Maybe the game has changed mentally, and I’m comparing myself versus my previous self and not just those around me.

Someone texted me, “When are you going to win something this year?” and I laughed, and thought, “Am I supposed to feel like a failure because I haven’t won a local race?” Some bad luck and ill preparation spoiled some races but these experiences have made me a much stronger cyclist, so that when I do hit the big stuff (Nationals, Master’s Nats, Tour of Southland, Gravel Worlds), I’ll have a better chance of performing well!

Oh, yeah, I did a Gran Fondo rather than a 15 man road race; it was awesome to meet new people, ride new roads, and hammer out 150 miles. Maybe the game isn’t changing; maybe I’m changing.

Always race up, even if it doesn’t mean winning; getting better at something is winning.

2019 GOALS

If I’m going to hit big races, I may as well try for big goals. Oh, that composite team thing; well I got asked to race Tour of the Southland in November in NEW ZEALAND!!! If you haven’t watched some of these stages on YouTube, you may as well start now.

But how will I race in November in a former UCI stage race, and not be burnt out? Usually, by November, I’m 45 days into drinking season, a few pounds heavier, and way less motivated to ride hard. (My drinking schedule has changed; I’m even more cyclical now, but on a micro platform; 90 days off, 1 day on.)

Then, Master’s Nats got pushed back to August.

There were very few road events scheduled for spring.

Well, change it up...start really ripping much later in the year, and look to have a killer July, August, September, Rest, NOVEMBER!

It was mentally difficult to not come out RIPPING in March like I usually love to do, but I knew that doing so would mean being burnt out for the biggest races at the middle and end of summer: Oregon Gravel Grinder (a 5 day gravel stage race), Masters Nationals, State Road Race and Time Trial, Gravel Worlds, River Gorge (now cancelled!), Tour of New Zealand.

The Days Before Stage 1

So, here we are, on the cusp of what all the training was for. With personal success but very few podiums to speak of just yet in 2019 (just 2), I came to Oregon hungry as hell.

The trip was a bit hectic, as travel plans changed last minute, and instead of a wild road trip, we all decided to fly. The DNA Racing roster was: 

Andy Chasteen, our fearless leader

B$ aka Power B, aka Brandon Melott, aka BMoney Racing

Patrice aka Patrick aka Patrick Walle


We were slated to meet up with Cailean Calberg aka Chamburgler and Rob Bell aka RobBellLife from Oklahoma, and maybe the Meteor Giordana crew of Colin Strickland and Kevin Girkins.

Oh PS, camping was involved and I’ve been camping twice and the one time it was just for a day so that doesn’t really count. 
I wasn’t sure what to expect from this, but was willing to give it a whirl: TRY NEW THINGS.

My Orucase was the bomb and I paid no baggage fees for the bike, and I didn’t even have to lie. I told the airline it was “bike parts” when they asked, which is 100% true. It was not a full bike as there were no pedals. Saved $125 each way; hello $250 in my pocket!

Made It To Oregon

After two transfers in MN and WA, I made it to Redmond and called a basic Lyft since my bike box/bag is now so small. You can get in the tiniest car and it will fit. It’s a game changer for sure!

I was super happy to make it to our host house (Thanks Marleen!) and put my bike together. Sadly, I tried to sabotage everything by losing a cap to my wheel and snipping the Di2 cable in my seat post. I inserted the seat post and there must have been too much slack, and the seat post slid over the cable and SNIP.


I felt solace knowing B$ was coming that night, but I didn’t want to waste any time. I got ahold of Sunnyside Sport and once I heard they had Di2 cables in stock, I felt a sense of hope.

Barb crushed it and the bike was rolling. After a shake out ride, I ended up getting a larger cassette with a 28 in the rear, and thank goodness, because I used every inch of that thing.

Photo by ME

Photo by ME

We rolled around and the bike felt good; I was a little worried about how I’d handle some of the sandier and rocky sections of the course, but hey, if everyone is on 36c tires, it’ll be a fair race. Lol, foreshadowing.

The rest of the crew slowly rolled in, and as Monday and Tuesday went by, we got excited for Stage 1. What was the Oregon Trail going to be like?

I couldn’t wait to find out, and man, riding in just a baselayer is such a jam.

Photo by Andy Chasteen

Photo by Andy Chasteen

Thanks for reading thus far, as I wanted to explain how a roadie got to gravel, and tune in over the next week or so as I post about the race experience; or so I plan to. It was a heck of a trip and would love to share more with you if you haven’t seen it all on Instagram.

Comment below on what your big goal race is! I’d love to hear how it goes!