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We have a Surly retreat coming up where we are packing up the bikes like donkeys and riding southwest to camp out, drink tea and wax-poetic about bicycles for a few days. I was onboard when the idea was tossed out but also intimidated.

I’ve always had a negative view of road bikes from my time working in shops. The skinny wheels and gnarled bars make me feel uncomfortable and confined. I like to ride where I want to ride. I do not want to be limited by a skinny bald wheel. It’s not my thing. Nor do I want to spend half an hour squeezing into skintight kits and adjusting my aerodynamic bits just so I can get on my bike. This was the idea I had of road riders. Skinny tires, skin tight crayola puke clothing and lots of high tech crap were required to successfully ride on a road for any number of miles.

The thought of riding 35+ miles loaded down with a bunch of avid riders who do this type of riding on a whim, made me nervous. So I decided to make an effort to get as much road time as possible before our trip. Rain or shine or severe winds as it were. I shall ride.

Riding to and from work regularly was helping but I was still able to stay within neighborhoods and take paths off of the street to make it into work. The big game changer was a ride into Lowertown St Paul for drinks and eats. It was a 20 mile loop and included climbs and city street riding. I had never ridden more than 16 miles in a day and never in the dark.

I prefer to ride in street clothes and shoes. So I wasn’t too geared up when I set out for my ride. Here is what I had:

  • Jeans
  • Cotton long sleeve shirt
  • Shoes
  • Cars R Coffins Sox (RIP little coffee shop)
  • Knog Frog Strobe white LED
  • Nathan LED Safety Strobe red light
  • Lock (last minute addition I almost forgot and that would have sucked)
  • Surly Long Sleeve Wool Jersey
  • Old canvas messenger bag
  • Shimano windbreaker 2 sizes too large that I found in my basement (I had left my jacket back in Surly land and winds were kicking at 26 mph+)
  • Old Fox helmet
  • Trusty Cross-Check

Downward view of clothing laying on pavement

All stuff I had lying around mostly. I had to buy the lights because my last set had disappeared probably 7 or 8 years ago.

I set out with a 26 mph headwind and pushed my way towards the city. I got lost, I went down steep hills, climbed steep hills, road through parking lots, on sidewalks, on bike paths, on roads, in bike lanes and on some dirt just cause.

I had a blast. I showed up and rewarded myself with fancy beverages and good eats.

Close of view of a stemmed glass of beer, on a granite counter next to a glass of ice water, in a bar

Downward view of a fried cheese curd on top of a white plate

I was pumped to ride home as the headwind would now be a tailwind and the 2 size too large windbreaker would now be a sail instead of a drag.

I rode much more road on the way home. My lights worked great. The weather was nice. The streets were actually quiet. I had to flip my bike for a quick chain fix but other than that my ride was smooth and uneventful.

Right side view of a black Surly bike, flipped upside down and standing on the seat and handlebar, on a brick sidewalk

I wasn’t even winded when I returned home. The next day I wasn’t even sore. I feel ridiculous now thinking I was worried about riding 20 miles of climbs and city streets. I honestly think you would too if you tried it. This was nothing epic. Nothing extraordinary. It was a hell of a good time.

My friends that do not ride heard about my little trip and were shocked to hear I did that. It amazed them. It would have amazed me too. It seems so far, until you do it. Then it’s not far enough.

Straight away view of a paved bike lane on the right side of a roadway with cars next to it