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That Time Kevin Hassled Me: A Hilarious & Painful Katy Trail Misadventure

  • Writer: Charmaine Warren
    Charmaine Warren
  • 3 days ago
  • 3 min read

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Hook: What Could Possibly Go Wrong?

Inspired by Uncle Doug’s legendary solo ride across Missouri’s iconic Katy Trail, Kevin and I (fueled by ambition and a concerning lack of foresight) decided to tackle the Rocheport to Boonville stretch—arguably one of the most scenic bike trails in Missouri.


Calm river at sunset with a green forested shoreline. Pink and blue sky reflects on the water. Trees overhang the riverbank. Mood is serene. Rocheport Katy Trail

Armed with enthusiasm, questionable planning, and a couple of bananas, we set out for what we thought would be a fun adventure. Spoiler alert: It was fun, but also a lesson in suffering.


Couple smiling in a sunny park near a trail sign. The man holds a bottle, and a bicycle is partly visible. Green foliage in the background. Rocheport Katy Trail

Starting in Rocheport: The Calm Before the Storm

Our adventure kicked off in Rocheport, MO, a charming little town that serves as one of the best launching points for a Katy Trail bike trip. Per Uncle Doug’s advice, we stayed at Briggs Pond B&B, a tranquil (and slightly eerie) spot with a strictly vegetarian breakfast. Luckily, the owner, Daria, saved the day by offering me some extra bananas—because let’s be honest, carbs are life when you’re about to pedal for miles.


A wooden shelter at Rocheport, MO trailhead, surrounded by trees. A sign reads "The Rail-Trail Hall of Fame." A parked car is visible. Rocheport Katy Trail

We spent the first evening enjoying Abigail’s Restaurant, a well-loved Rocheport gem, before heading to bed, blissfully unaware of the pain that awaited us. Abigail's is unfortunately permanently closed :(


Charcuterie board with sliced meats, crackers, radish, pickles, mustard, and cheese on wood. Vibrant colors, inviting presentation. Rocheport Katy Trail


Hitting the Trail: The First 12 Miles Were Actually Fun

The Katy Trail in Missouri is stunning, and for the first part of our ride, we soaked in the breathtaking views. Towering limestone bluffs, the Missouri River, historic MKT railroad signs, and even a cave that once stored dynamite made for some incredible photo ops.


Bridge with red railings leads to a forest tunnel. Lush green trees surround the scene under a clear blue sky, creating a serene mood. Rocheport Katy Trail


We were making great progress until hunger hit. Enter: Cooper’s Landing—a riverside oasis with Thai food and ice-cold water. It was here that I, in a moment of overconfidence, declared:


Bicycles parked near a river with helmets on handlebars. Picnic table and "No Dogs" sign visible. Trees and clear sky in the background. Rocheport Katy Trail


Two plates of food: one with noodles topped with peanuts, another with grilled skewers, rice, sauce, and pickles. Two Dasani water bottles.

"Hooray! Now we can go 10 more miles!"

And Kevin, being Kevin, agreed.


Two bikes rest on a sunny path lined with lush green trees. A sign reads "PROVIDENCE." The mood is serene and inviting. Rocheport Katy Trail


Regrets, Pain, and the Never-Ending Trail

By the time we reached Wilton, we had officially run out of enthusiasm. My legs felt like jelly, and Kevin, ever the optimist, convinced me to push to Hartsburg, where (and I quote) "they have fancier restrooms."


Two bicycles rest beside a "Wilton" sign on a leafy forest path. Sunlight filters through the trees, creating a serene atmosphere. Rocheport Katy Trail


Reality check: This just meant toilet paper and a sink.


After 24.26 grueling miles, we finally reached Hartsburg—exhausted, sunburned, and slightly regretting our life choices.


Two bicycles lean against a sign reading "Hartsburg" in a lush, green forest. A wooden bridge labeled "Hart Creek" is visible in the background. Rocheport Katy Trail


The Ride Back: Pure Suffering

After some much-needed hydration and stretching, we faced the cold, hard truth—we had 25 miles back to Rocheport.


Charmaine & Kevin smiling on a bridge with lush green trees in the background. The man wears a Nassau cap, and the woman has sunglasses. Bright, sunny day. Rocheport Katy Trail


We were too tired to take pictures, too sore to talk, and too stubborn to quit. Every mile felt longer than the last, and let’s just say I’ve never been more grateful for padded bike shorts (even though mine weren’t nearly padded enough).


So what did I do? I took my sweet time of course! I was tired. My water was tepid and it was hot. What did Kevin do? Hassled me to "STOP LOLLY GAGGIN" to which I responded with "I am not lolly gagging... I am truing to enjoy the scenery. It is not my fault you have no appreciation of nature"


Lessons Learned: What You Should Do on the Katy Trail

  1. Invest in proper cycling gear. Those padded shorts are lifesavers. Trust me.

  2. Bring more water than you think you need. Frozen bottles work best in the summer heat.

  3. Slather on the sunblock. Otherwise, you’ll look like a boiled lobster.

  4. Pace yourself. Just because you survived Insanity Max 30 doesn’t mean you’re indestructible.

  5. Enjoy the journey. Because at the end of the day, pain fades, but the adventure (and the hilarious stories) last forever.


Would We Do It Again?

Absolutely. The Katy Trail Missouri experience is a must for cyclists, despite the sore muscles and minor existential crises along the way. Next time, though, we’ll actually listen to Uncle Doug and take it in smaller segments.


Stone tunnel with rough, mossy walls and a path leading to bright greenery. Sunlight highlights rocky textures, creating a serene mood. Rocheport Katy Trail


So, if you’re planning a Katy Trail bike trip, don’t be like us—plan smarter, hydrate better, and for the love of all things holy, respect your limits.


Unfortunately Briggs Pond is already closed but you are free to chose many other Bed & Breakfast places in the area which are happy to make recommendations on restaurants.

You can use this link to look for VRBOs in the area


🚴‍♂️ Ready to Ride the Katy Trail? Share Your Adventures in the Comments Below!

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