Larry Myers

Cover Image for The Perfect Solitude of Endurance Cycling

The Perfect Solitude of Endurance Cycling

It’s around 5:15am on a warm morning in mid-June. I’m climbing the long shallow hill up to the top of the Fullerton overpass along the Lakefront Trail. It’s early enough there isn’t much traffic on Lakeshore Drive yet, so it’s still relatively quiet in Chicago. The sun is still below the horizon, but the sky is starting to turn a soft orange where it meets the lake. After crossing the overpass I get my first full view of the downtown skyline. It is worth waking up early for.

Ten minutes later I’m pedaling hard along Oak Street Beach, enjoying the effort it requires to keep a steady cadence at 18mph. The sun is rising and I stop to grab a picture.

Sunrise over the Lake Michigan

After cresting the flyover I decide to make my turnaround point in Grant Park and don’t devote much brain power to figuring out a route home. I’ve been enjoying Lincoln Ave lately, but I’ll just take the turns as they come and see what I feel like.


It’s a warm summer evening in Chicago, and I’m waiting at the light on Upper Wacker. People give me a funny look when I say I like to ride Upper Wacker, but since the pandemic the loop doesn’t have the same volume of traffic and doesn’t feel as risky. My lights are on, and I’ve got the right lane to myself. I’m optimistic I can keep up with the light cycles and make it to Lake Ave before I have to stop again.

Upper Wacker at Night

I’m now pedaling south after rounding Wolf Point and take a few moments to admire the Lyric Opera. I decide to turn at Adams and explore the West Loop before working my way back north. Getting in around 25 miles tonight will still get me home before it gets too late.


It’s winter in Chicago, and February is the worst month here. The Skokie Valley Trail has been plowed and the studded tires feel like overkill at this point. Better to be safe though and not have to keep such a watchful eye out for patches of ice. It’s cold, but not enough to prevent me from staying out for a few hours and enjoy having the trail to myself. One of the joys of winter cycling is never having to say, “on your left”. Most people put their bikes away months ago.

Happiness is a Plowed Trail

The trail ends, and I decide not to connect with the North Branch Trail. Last week the snow was too rutted and packed to be enjoyable without a fatbike, which would see too little use for me to ever consider buying one. I head east on Bryn Mawr just as snow starts to fall. It should be a nice ride home.


Riding a bike for long stretches of time has been a constant for me over the course of my life. I suspect it has become a necessary activity for maintaining my mental health. As a software developer there is something very calming about a physical activity that demands my focus and attention, and requires me to put away my phone and step away from my desk. So much of my career involves building things with no physical substance. Cycling is the opposite. You interact with a machine that directly responds to every input you give it. In the city it requires your full attention. There is no room for work problems to intrude. On the trails you can let your mind wander, and in nature it’s hard to focus on anything technology related.

When I find myself stressed I know I need to fight against my worst impulses to procrastinate and do nothing, confident that just getting on my bike for at least 90 minutes will solve my most immediate problems. It is different than planning for a group ride with friends, which is first and foremost a social event. The purpose of these solo rides is to deal with my problems through prolonged physical exertion. It’s the least expensive form of therapy available at times.

Go ride, you’ll feel better. Pedal hard, push through the headwinds, and go explore.