Our First Motorcycle Road Trip Begins
Illinois to Evansville, Indiana

Every motorcycle trip has to start somewhere, and ours started in the familiar cornfields of central Illinois.

We’ve taken plenty of shorter rides together, including a few overnights, but this was something different. Six days on two motorcycles, heading toward Tennessee and North Carolina to ride roads we’d been looking forward to for a long time. The Cherohala Skyway, Tail of the Dragon, Foothills Parkway, and Moonshiner 28 were all on our wish list. Whether we’d manage to fit everything into the trip was another question.

Our first day was a relatively easy one, covering about 200 miles to Evansville, Indiana. It’s a route we’ve ridden before, so there wasn’t much unfamiliar territory yet. We stopped in Casey, Illinois, where we made one of our first attempts at talking to a camera in public. Sitting in a McDonald’s parking lot discussing our plans probably wasn’t the most glamorous beginning to a motorcycle travel channel, but you have to start somewhere!

Our next stop was Olney, Illinois, for fuel and lunch at Arby’s. Nothing particularly adventurous, although Kennie was happy to share his discovery that asking about unadvertised manager specials can sometimes get you a better deal on lunch.

From there, we continued south toward Evansville on our two very different Yamahas. Kennie’s V-Star 1300 is a comfortable cruiser, while Chris’s little MT-03, Myrtle the Turtle, is lightweight and nimble. Both had served us well on shorter rides, but we were about to find out how we’d feel after several consecutive days in the saddle.

We reached Evansville after roughly five hours, including stops, and checked into a hotel at the casino overlooking the Ohio River. We weren’t there to gamble, just to enjoy the view, relax, and get some rest before the longer ride ahead. We even spotted a rainbow while looking out over the river.

The following day was the one we were really thinking about. We hoped to cover more than 300 miles and make it all the way to Athens, Tennessee, although Crossville was our fallback if we’d had enough riding for the day. Rain was in the forecast for late afternoon, and we wanted to get as far as we comfortably could without turning the trip into a race.

Day 1 wasn’t full of dramatic mountain curves or unexpected adventures. It was mostly familiar roads, fuel stops, fast food, and the excitement of finally getting underway. But sitting beside the Ohio River that evening, knowing we were about to ride farther from home than we’d ever gone together on motorcycles, made it feel like the beginning of something pretty special.