101-Mile Bike Ride

I just recently completed a 101-mile bike ride.

I started at Cave-in-Rock Ferry in Cave-in-Rock, Illinois. I was supposed to finish the ride at Saint Nicolas Brewing Company’s Landmark in Chester, Illinois.

I couldn’t finish the ride in Chester, and I knew I wouldn’t have been able to from the start.

This is my ride log and story of my longest and hardest bike ride yet.

The 101-Mile Bike Ride was Supposed to be a 135-Mile Bike Ride

The ride was supposed to be a 135-mile bike ride.

The route starts at Cave-in-Rock and ends in Chester. It’s the southern Illinois portion of the Trans American Bike Race route, which is a bicycle race that has been going on every year for many decades.

This ride was called SOIL TransAm and was formed by the Saint Nicolas Brewing Company Cycling Club. I’ve been a club member for quite some time, although I need to pay my dues and haven’t really ridden with the group in quite a while.

Work and life get in the way of things.

The ride was supposed to be 135 miles and nearly 8,000 feet of elevation gain, which would have been the longest and hardest road bike ride ever.


Training Failure

The ride was on Saturday, June 17, 2023, at 6:00 AM CST.

I had been registered and aware of the ride for a few months before the start date. I failed (miserably) at training for the ride because I didn’t train for the ride.

I could have. I live in Massac County, Illinois, with pretty good-sized hills. I should have been riding and hitting the hills as much as possible.

But I didn’t because I quit my job after 13 years. I was in the process of preparing for my new career. I just kept putting training off.

I did ride still. I mountain biked once a week, rode at Tunnel Hill, and did a few flat road bike rides here and there. But I didn’t ride like I should have.

I also dropped about $600 worth of repairs on my road bike.

I think the failure to train was my downfall, but I still managed to do a 101-mile bike ride at the end of the day.

101-Mile Bike Ride

What I Did Right

The repairs I got on my road bike were the right thing to do.

I had a new drivetrain put on, along with a new chain. I had my handlebars wrapped. I got new tires and tubes and had new spokes put in after busting one out.

The repairs made riding my bike much smoother and made everything a little safer.

Michelle (my girlfriend) insisted I wear my WILDCYCLER kit, which I had planned to wear anyways. The kit is really bright and wildly colored and patterned. It has pink, baby blue, green, and yellow patterns. I wore it for two main reasons.

(1) It’s super comfortable. It fits perfectly, and the chamois (pad in the bib-shorts) was thick enough for that many miles in the saddle.

(2) The wild print and colors made me stand out like a sore thumb. Drivers would have instantly noticed me on the road, and they did.

I highly recommend WILDCYCLER cycling kits. Not only because they’re comfortable and great for being noticed but also because they’re fun and made in the USA. They have plenty of wild pattern options for both men and women.

I also tried Chamois lubricant for the first time. You apply This cream to your chamois (the pad in your bib shorts/bike shorts) to help reduce chaffing during long-distance cycling. I always skipped using it before because I thought it was weird. I also always hurt on long-distance rides before I started using it.

I bought the brand “Chamois Butt’r” for this ride, applied it, and will now always use it on any bike ride over 30 miles. That stuff is to die for! I never felt one ounce of pain from the saddle for the whole 101-mile bike ride. It worked way better than I thought it would.

I ate right the morning before the ride. I had a banana and some oatmeal. I had one cup of coffee. I usually drink several cups, but more than one cup would have made me want to poop. Sorry to be blunt, but that’s what coffee does to me. I don’t want to get a sudden urge to poop while on the bike away from restrooms.

We ate at the Cave-in-Rock Kaylors’ Lodge the night before the ride. Their mushroom Swiss burger is good. I recommend eating there.


What Went Wrong!

Aside from the training or lack of training, some other things went wrong.

I didn’t sleep that much the night before the ride.

We camped in a tent at Cave-in-Rock State Park campground. I can usually sleep great in a tent, and our campground was very nice. But the quarry down the road from it wasn’t a nice benefit.

It sounded like we slept right next to the quarry all night.

It was one of the loudest things I’ve ever heard and lasted most of the night. I went to bed at about 9:30 PM and finally fell asleep at around 2:00 AM. I woke up for the ride at 4:50 AM.

I told Michelle I wouldn’t ride it that night because the quarry kept me awake. But when I woke up, I talked myself into doing it anyways.

No offense to the quarry – I know the job has to get done, and it’s work for people. I’m not upset with anyone. Jobs are important. I just want to ensure that no one thinks I am mad at anyone. It was no one’s fault, really.

The next thing that went wrong was that my lack of training caught up with me quickly. Once I started hitting steeper hills, I had to unclip and push my bike up quite a few of the hills. So, I started with a group of cyclists at Cave-in-Rock and quickly lost them on the first few hills.

I figured this would be the case and told them that I didn’t train the night before and would be slow and likely last to show up.

And I’m fine with that.

Ultimately, the hills and the heat (and my lack of training) were why I rode 101 miles, not 135 miles.

I also didn’t hydrate as much as I should have, but I tried to drink more than usual. I have to give myself an A for effort for at least trying to hydrate properly.


Made a New Friend

Another cyclist on the ride was also having problems – mechanically.

Her derailleur was broken and missing a part that allowed it to properly shift her gears. So, she had to unclip and push her bike up the steeper hills.

I caught up with her around mile 30ish, and we stuck together all the way to the end. I’m glad, too, because it motivated me to keep going. And I’m sure it motivated her, too.

We ultimately agreed that we wouldn’t be attempting to complete the full 135 miles, but we wanted to do at least a 101-mile bike ride because it would be the longest ride either of us had done. We both have been 100 miles, so one more mile would put us over the edge.

I knew from the start of the ride that I wasn’t doing the whole thing. My lack of sleep and training was what made me know that. But I’m happy about what I did, which mattered at the ride’s end.

Thanks to my new friend for the company!

And thank you, Michelle, for always believing in me.


Heat, Hills, and Hard Last Miles

The heat was getting to me. It was over 90 and humid. It was also mostly in the sun. Walking up hills was tough in the blazing humid sun.

Some of the hills were monstrous. The worst one was the hill past the equine building right after you pass the Regent Road turn-off on the Goreville Blacktop heading toward I-57. That was the worst hill out of the whole ride for me.

Route-wise – I hated biking on Gilead Church, Tunnel Hill, and Grassy Roads. There are no shoulders. They have so many winding road portions. They have a rollercoaster of hills. And one of them roads had a pretty mean German Shepherd following my a surprise Great Pyrenees that wanted to eat us both.

People who let their vicious animals run loose shouldn’t be allowed to own animals…

The last few miles were rough. I was hot. The hills had done me over. And I was feeling sick. The last mile to where we decided to stop was almost impossible for me to do. I sat in the grass and waited for Michelle to pick me up.

She had been monitoring my location on Live360, so it didn’t take her long to get there. I love you, Michelle. You could have had a whole day to yourself to do whatever you wanted, but you aided me instead. She did get to take my truck on the ferry and over the Amish country in Kentucky, though.


Conclusion of my 101-Mile Bike Ride

I will try again next year to complete the full 135-mile bike ride.

I’ll just make sure I train for it.

I am very satisfied with my ride, however. I don’t feel like I failed at all. I rode the longest and hardest ride I’ve ever ridden. To me, that is a victory. That is worth celebrating.

After the ride, I ate at Whiffle Boys in Goreville, which always hit the spot.

I hiked 6 miles the next day, too.

Nothing really hurt after the ride. I just felt tired. It’s been a few days since the ride as I wrote this article, and I still feel a little tired. I’m also thirsty more throughout the day, so I probably got dehydrated a little.

Also – It was fun to see the Trans Am racers and adventurers riding eastward as we traveled westward. Some of those riders average over 200 miles a day on their bikes. That’s tough!


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Shawn Gossman

Shawn Gossman

Founder, Hiking with Shawn

Howdy folks! My name is Shawn Gossman and I founded Hiking with Shawn. I’m an avid hiker, cyclist and outdoorsman here in the Shawnee National Forest. I was born and raised in Southern Illinois and never want to leave. Click here to learn more about Shawn Gossman

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