Day 0.5: Split Squads, Small-Town Networks, and the 168-Mile Soak
The waiting is finally over. Kickstands are up, the exhaust notes are echoing, and the great Route 66 run is officially underway. Day one is all about breaking in the gear, adapting to the weather, and discovering that on a motorcycle road trip, there’s no such thing as a wrong turn—only unexpected detours.
We ran this opening leg as two separate crews, charting different paths from Tennessee into the heart of Missouri. Here is how the rubber met the road on day one.
Mike & Andy Dean: Burgers, Bureaucracy, and a Monsoon Push
We packed up the bikes and were rolling by 8:30 AM, making a quick first stop at Dean’s shop. The mission? Piece together our new Sena S50 communication systems so we could actually talk to each other at 70 mph. We finally cleared out of the shop around 10:00 AM, pointed the front wheels west, and cruised into Arkansas.
Our lunch stop in Little Rock was a happy accident. We completely missed our intended exit, but the mistake paid off beautifully when we stumbled upon Dave’s Burgers.
[ ROAD CHEF REVIEW: DAVE’S BURGERS ]
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Location: Little Rock, Arkansas
The Vibe: Casual, no-nonsense burger joint.
The Verdict: Missing our exit was the best thing that happened
to us all morning. Outstanding, juicy burgers that
hit the spot perfectly before the skies opened up.
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As we were wrapping up lunch, the weather gods decided to test our resolve. The sky turned an ugly shade of gray and down came the rain. We bundled up in our heavy rain gear and settled in for a brutal, 168-mile stretch of continuous downpour.
The guy in the car right in front of us claimed he knew a shortcut, but since it involved taking heavy touring bikes down a muddy gravel road in a rainstorm, we politely passed.
The Highway 65 Standstill
About 70 miles outside of Branson, Missouri, traffic on Highway 65 ground to a dead stop. We found ourselves stranded on a highly unforgiving, curvy, slanted section of asphalt. For 45 minutes, we sat there in the pouring rain, eventually getting off the bikes to stretch our legs and chat with the drivers stuck in the gridlock around us.

Then we met Shirley. A local from the car behind us walked up and told us she knew one of the sheriffs who had just sped past, and she was literally going to give him a call on his personal line to find out what was going to happen. Right about then, an ambulance came back down the road, and the guy driving it turned out to be the local mayor! Shirley flagged him down, and he rolled down his window to chat. He let her know they were opening the road up to a single lane in just a minute.
Shirley was an absolute classic—the kind of small-town force of nature who knows literally everyone. I’m convinced if we had stood in the rain talking to her for another ten minutes, we would have discovered a mutual friend.
It turned out a semi-truck and a small car had gotten into an argument on the highway. Once the lane cleared, we snuck past the wreckage and finally cruised into Branson.
To wind down from a high-stress, high-water day, we treated ourselves to an incredible dinner at Florentino’s Italian in Branson. It was a relaxed, delicious end to a 360-mile trek. We headed back to the hotel room, fine-tuned our helmet comms, and dried out our gear.
Pete & Blake: The Night Shift and Missouri Bugs
While Mike and Andy were battling the Arkansas rain, Pete and Blake had a very different start to the trip.
Pete wrapped up his workday early that afternoon, and he and Blake immediately throttled out. After battling some agonizing, agonizingly slow stop-and-go commuter traffic on I-24, they finally broke out into the clear and made good time, crossing over the massive bridges spanning the Ohio and Mississippi Rivers.
By the time they pulled into Poplar Bluff, Missouri, complete darkness had settled over the landscape.
Every rider knows the unique pain of a late-night push. As Pete noted: “It is incredibly hard to ride a motorcycle at night with your sunglasses on… but it is infinitely harder to ride at night in Missouri with massive bugs violently exploding directly into your eyeballs.”
Despite the insect assault and the darkness, the boys kept the rubber side down and successfully secured the northern front of day one.
The Day .5 Stats
- Total Mileage: ~360 Miles (Mike & Andy)
- Rain Meter: 168 Miles of pure saturation.
- Lessons Learned: Missing an exit usually leads to a great burger, small-town networks are faster than GPS, and always change out your tinted visor before the Missouri night bugs wake up.
Next Stop: Regrouping the pack and pushing through the Missouri woods toward Oklahoma! Keep the shiny side up, friends.
