I completed my longest bicycle ride to date, 29.3 miles. This ride had a few more milestones as well and some lessons learned that I will discuss here.

It’s the middle of Fall, the days are getting shorter, and dry weather is becoming the exception, not the rule. Fortunately, there was no precipitation on my day off, so my buddy, Keith, and I decided to get out on two wheels for a ride around Washington County.

When we met in the empty parking lot at Liberty High School in Hillsboro, Oregon, it was 38 degrees and foggy. This would be my maiden ride on my brand new bike, a Trek Domane AL 5. I literally had never sat on the bike until that moment, and in fact it was also my first time riding with clipless pedals (although I have recently installed the same pedals on my spin bike at home).

Keith and I did a few laps around the parking lot so I could get used to clipping in and out of the pedals, as well as learn the hand signals cyclists use on group rides. Once I got the basics down, we set off.

The entire route was on public roads. Up to this point in the season, I have ridden exclusively on designated bike paths without having to deal with traffic (other than one day climbing the numerous hills of my own neighborhood, where everywhere you go is uphill both ways). Keith led and I followed.

It was a bit chilly at first, as you might imagine, but my gear did well at keeping me from getting too cold. I wore full-finger cold-weather cycling gloves, which were probably overkill by the time we’d ridden 5 miles or so. I also had to unzip my outer shell jacket to regulate my body temperature.

The route we took went counterclockwise around highway 26, the Sunset Highway, taking us on rural roads through some beautiful farm country. Most of the time we were on narrow two-lane paved roads without anybody around. It was nice to ride side-by-side with my friend, at a pace where we could hold a conversation.

There were some small roller hills to contend with and Keith gave me advice on how to prepare and handle them. I’m not yet in shape to handle hills of any extent, but I’m getting there. Overall, I was able to complete the ride without nearly as much struggle as I had expected.

About three-quarters of the way we came upon another cyclist riding a single speed bike. As I passed by I said, “Hey, you look familiar.” It was Keith’s wife, Meagen, riding a portion of the same route. The three of us completed the remainder of the ride together.

By the time we got back to my car, we had ridden 29.3 miles in 2 hours, 15 minutes. It was my longest ride to date. Note: It is my goal to ride 100 miles by October of next year. I guess I’m 29% of the way toward reaching my goal.

What was noteworthy about this ride is I was using a bike I had never ridden before. I had recently purchased it from The Bike Gallery in Portland, after getting professionally fitted by Zak Kovalcik. The Trek Domane AL5 performed wonderfully. Although I had conceptually understood the value of a professional fitting, I could recognize its worth in a very tangible way on this ride.

I had very little problem clipping in and out of my pedals, but I still need to burn into muscle memory the way I shift gears on the drop-style handlebars. I’m used to the old style of mountain bike shifters where you use your thumb and forefinger. It won’t take me long once I’ve gone on a few rides.

I have decided to nickname my bike Riff Raff, after the AC/DC song and the character from The Rocky Horror Picture Show.