Let's go on an adventure!

September 30, 20238 minutes to read

An unusual and exciting, typically hazardous, experience or activity.

In August 2023 I rode my bike across the Green Mountains of Vermont, zig-zagging over mountain passes, abandoned logging roads, and working dairy farms. It was the most demanding endurance challenge of my life (I think). It provided an extended opportunity for reflection on why we do hard things.

By the Numbers:

DistanceElevationRide TimeEnergy
417.43 km5960 m22h 21m9495 kjul
259 mi18,667 ft

Photo Gallery


Why Go On An Adventure

Everyone I told about my plans had an effusive reaction: "That's so cool!" That kind of enthusiasm validates my decision to go but I still wanted an intentional reason for putting my time & energy into this.

I have a mild case of wanderlust

I've always loved to travel. It stops short of selling all my possessions and buying a sailboat. 😅 I just don't like sitting still. I've written about my love for travel and my belief it makes people more empathetic, wiser, and well-rounded.

I also have a well-documented love of cycling. One of my favorite aspects of cycling is the pace and altitude. Cycling is the best way to see the world.

“It is by riding a bicycle that you learn the contours of a country best, since you have to sweat up the hills and coast down them.” – Ernest Hemingway

Paradoxically for me, these two passions have never intersected. Bike touring has intrigued me for years but only as a fantasy that I haven't fit into my life. The brightest silver lining of being laid off is that it opened most of the space I needed to give it a shot. The layoff wasn't the reason, it was the excuse.

Going on an adventure gives you a heightened sense of reality.

Most of what you perceive to be real on a routine day is a framework constructed by your brain based on past experiences. Processing and framing the flood of stimulation in everyday reality is energy-intensive. The human brain will do just about anything to avoid extra work. You may think you taste your morning coffee but what you are perceiving is the brain replaying what it has tasted in the past. "Oh coffee? I know what that is. I don't need to figure it out again."

One of the popular theories for why we have dreams is a deferred processing technique for brains to understand the events of the day and correlate them against previous experiences to enrich their meaning. We can't fully understand the world in real time.

This gateway our brain is trying to put in front of us is why new experiences seem so much more, vibrant or frightening or whatever. That's reality breaking through the brain's defense. Venturing outside of the routine routine forces your brain to confront what is happening.

Type 2 Fun is Still Fun.

It'll be fun when it's done. The suffering is temporary but the glory is eternal.

People can do hard things; things like riding a bike uphill, on soggy gravel, for 65 miles, day after day. Taking on demanding challenges provides us with purpose. Ambitious goals drive progress because goals force us to strive for our best effort. The best goals should feel just out of reach.

I had rarely ridden more than 100km in a day before this tour. On those few occasions that I did break that arbitrary limit, it was riding a lightweight road bike rolling on smooth tarmac. The terrain, surface, and distance I planned for this ride were intentionally outside my physical comfort zone.

Riding this route well would require me to train my body. I couldn't just hop out of bed and bang it out. I had to do the work. I'd be setting myself up for a world of suffering otherwise. I could have done it but it would have been closer to survival than type 2 fun.

After The Ride: Reflections and Ruminations

Riding your bike alone for four days provides a lot of time for reflection. Some of the themes were cliché and some of them might be novel...

You should go on an adventure every year.

This is a cliché for a reason but you really should go chase your dream adventure. If there’s something you’ve always dreamed of doing - going on a bike tour, visiting a country, starting a business - you can do it! You can overcome the obstacles that are stopping you.

The mountains in the future always look like molehills in the past.

The Human Body Is ... Amazing

You can do more than you think you can. Your legs will send messages of pain with every pedal stroke. Your mind will start bargaining. "If I just make it to the next gas station, I can stop." Pay those messages no mind. The Fear is a safety mechanism that your brain can overcome. True success is achieved by breaking through those limits.

Endurance riding is about mind over matter. If you don't mind. It doesn't matter.

I did my best to physically prepare for this ride but there are limits to what you can do before the moment of truth. Each morning my legs were a little stiffer and the bags under my eyes a little darker. Just 10 minutes into riding each morning my legs would feel on fire triggering... The Fear. "Maybe i can't do this."

Yes, you can.

Your body will adapt to stress at astonishing speed if you make it. Know that you can conquer The Fear if you can recognize that this suffering is impermanent. After 20 minutes the pain will stop. After 60 minutes your strength will return. After 180 minutes you'll forget that you ever felt any discomfort. Just turn the pedals over one more time. Now do it again. And again.

To fully test these limits I planned the single most difficult stretch of the trip on the last day. After 350km of riding and 4500m of climbing I arrived at the base of the Lincoln Gap, which included the 2nd steepest paved kilometer in the United States. Oh, and it rained that morning.

It's about the smiles, not the miles...

Vermont is a gorgeous outdoor paradise. Colonial French settlers named the area Verde Monte because of the lush, verdant, mountains. The state attracts visitors all year round. Maple festivals in early spring, mountain meadows & secluded swimming holes beat the summer heat, stunning fall foliage, and of course winter Skiing.

It's busy, except... Summer weekdays.

I found that most towns I stopped in were very quiet. Many local businesses shut down Monday - Thursday. Good food & drink is one of the great joys of travel and I planned my route through towns known to have good restaurants & cafes. In practice, I often found myself scrambling to find whatever was still open and had fresh food.

Cycling is a team sport

I never could have done this without the support of my wife. She gave me the time and space to prepare, focus, and go on this adventure. In turn, I will support her in an adventure.

Planning The Route

Planning a good route is a design challenge. You need to consider your goals, constraints, and assets. Then map those against the variables of terrain, weather, and public services. It's emotional labor to find the route that produces the ride you want.

These were my requirements for the route:

  1. Maximize time in the state parks rather than towns.
  2. Prefer gravel over tarmac.
  3. No camping (I like good food and espresso).
  4. Trust the "popular" routes on heatmaps from Strava and Komoot.
  5. Climb over hills, not around.
  6. Fixed start and endpoints from Lee, MA to Montpelier, VT.
  7. My stamina for riding each day.
  8. Find a way home.
  9. Services are open during the mid-week in summer.

My first draft followed the Connecticut River along the border of Vermont and New Hampshire. This idea was an early inspiration for the ride: to follow the entire length of the Connecticut River from Saybrook, CT to the border of Quebec, Canada. This idea quickly proved too ambitious for a first tour. It also followed roads that were, frankly, not very interesting for cycling. Investigations into gravel back roads veered too far from the CT River which undermined the core narrative.

route along ct river

My second draft route tried to plan the route around dining. I mapped out the best farm-to-table restaurants in Vermont and tried to navigate through them. Unfortunately, this broke my first principle of maximizing time in nature. Most of the best dining options were in Rutland, Brattleboro, or Burlington.

route along ct river

Third, Fourth, Fifth draft I settled up with a route that zig-zagged through the green mountain forest while ending each day in a civilized town center.


I hopped back and forth between three different apps: Strava, Komoot, and RideWithGps. They each had their strengths.

Ride with GPS was the best route for a power user but getting the route loaded on my phone wasn't straightforward. It also had the clumsiest live tracking features.

Komoot had good organization features for breaking a tour into pieces, and it had live tracking with a profile of the ride, but it often chose routes that weren't passable.

Strava had a great route planning tool for individual days and integration with my cycling computer but didn't make it easy to zoom out and plan the entire tour. Strava's live tracking also doesn't show the ride profile.

Ultimately I used Komoot for the trip because it had the best mix of route planning features and live tracking.

The Bike Rig & Gear

The right tool for the right job. Some people really care a lot about this so here goes:

The Bike

The Bike

Notable Gear



Only what you take with you. –Yoda

Just kidding. I had two bags: