My Long Way Round – Part 1

It all started in early May after I took a week to explore the Appalachian mountains. The day after I arrived back home I felt a little lost and immediately starting thinking about my next trip to take. I loved riding through the mountains so the next best place was the Rocky Mountains for me. For the next three months I spent hours planning, preparing and researching for the trip. I used Google Maps and Wikipedia for the majority of my planning. Besides that the book, Motorcycle Journeys through the Rocky Mountains, was extremely helpful as I traveled through Colorado. Motorcycle Touring for Beginners gave me a long list of items to consider packing that I would have forgotten about had I not come across this site. Also, Motorcycle Camping Made Easy made my camping while motorcycling…less difficult. Despite my anal planning I did manage to forget two things. Chap stick and a flask of whiskey. The former was easily obtainable, but the latter was longed for a couple times after a hard day of riding.

This was my longest trip I have taken, both in mileage and time. I spent two weeks on the road and traveled 4826 miles. That’s about 70 hours in the saddle. Here is a daily account of my trip, and some of the interesting encounters and situations I came upon along the way.

Origin: Chicago, Illinois
Destination: Minneapolis, Minnesota
Mileage:450 miles


I left home around 9am. I took the same expressway that I took to work everyday and it felt very weird blowing by the Ogden exit ramp and continuing forward. That marked the beginning of my journey in my mind. I spent the majority of the day passing through Wisconsin. I kept thinking back to college and debating whether or not I should take a detour through Green Bay for old times sake. This was the closest I would be for a very long time, so why not? I thought about walking through the campus, perhaps running into an old professor. If I was that close I would have to stop by my old apartment where I lived with my ex-girlfriend for about 3 years. Perhaps catch dinner at what used to be our favorite Friday night restaurant? I began realizing what a dismal detour this would turn into so I continued on to Minneapolis.

The ride was boring, and just something to get out of the way. The only eventful thing that happened was when I got into Minneapolis. I accelerate forward from a stoplight for about 50 feet. I get this itchy sensation in the middle of my chest. It turned from itchy to pinching, to hot, to burning to excruciating. The son of a bitch in front of me ashed their cigarette and an ember flew into my jacket. Knowing that it was going to take me at least 10 seconds (which felt like an eternity) before I can get it out only enraged me. I brought the bike to a screeching halt on the side of the road, flung off my gloves and ripped off my jacket. The pain stopped growing, but it continued to sting. My roadside fit of anger was met with looks of confusion by passing cars. Never ash with a motorcyclist behind you.

I stayed with my sister who put me up for the night. It was nice hanging out with my sister and I felt like it was long overdue. I was only halfway to the border and anxious to get into Canada.

Origin: Minneapolis, Minnesota
Destination: Winnipeg, Manitoba
Mileage:550 miles

I woke up late and scrambled to get on the road. It was a very hot and humid day. A heat wave was blanketing Minnesota and North Dakota. As long as I kept moving I was comfortable. I only let myself stop for the necessities: Food, gas and smokes. An elderly couple from Grand Forks were watching their grand kids. My Illinois plates are the start of most my conversations while on the road. People wonders where I am going, or where I’ve been. I describe my journey, only in its infancy at the moment, and only until I vocalize it does the breadth of the trip truly set in.

North Dakota was horribly boring but luckily I only hit a small portion of it while traveling to Winnipeg. The main reason I traveled into Canada was to avoid North Dakota and Montana. It cost me 500 extra miles of riding, but it was well worth it. “US BORDER – 30 MILES” lifted my spirit. I’ll be in Winnipeg in two hours.

I arrived at the border. The man in the booth asked about my the nature of my travel into Canada and asked all the typical questions regarding firearms, tobacco and alcohol. He directed me to the immigration office since I had not entered Canada since I was 7. I got the 3rd degree from the woman behind the counter. She reiterated all the questions I had been asked before along with a myriad of others. How much cash am I bringing into Canada? How much money do I have access to via credit cards and bank accounts? Have I ever appeared before a judge in court? Have I ever been denied entry or been thrown out of Canada? This went on for about five minutes. She told me that she had to perform some checks and told me to take a seat. I felt like I wasn’t going to be allowed in. I already began mentally mapping out an alternate route through the US to the Rockies when it was interrupted by a call from the immigration officer. They finally let me through and I made it to Winnipeg.

Tomorrow was going to be a big day for me. I wanted to try and travel 800 miles. The most I’ve done in a day was 600 and I am usually exhausted at that point. It would be nice to spend more time in Canada, but setting a faster pace would allow me more time in the Rockies which is what this trip is all about.

I am going to split this entry up. Probably just talk about two days at a time. Stay tuned for more.

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