On Underestimating the Start


I’m driving across the United States for two months. My trip will take me around the country in a big circle, starting and ending in Massachusetts. This is the first blog post of the trip, reflecting on the first week of the journey, where I drove across the Northeastern Seaboard, Maryland, Kentucky, Missouri, and Kansas.

My trip began where it had to begin: on the east coast. I set out from home, in Massachusetts, for a trip around the country. My odyssey. My journey to recover after the year and a half of covid. My journey to find something of myself again.

Why does every journey have to have a purpose? I’m not sure that they do, but for me, I’ve found I get more out of a journey if I go into it with an intention. For this one it was, explore the outdoors of the United States. Do the adventurous things I’ve only ever thought about. Backpack Colorado, mountain bike Moab, camp in Glacier.

You’ll notice all these things take place in the west. The west was the goal. The point. The whole idea.

The East, the South, The Midwest, the Plains, these were places I just had to get through, in order to get to the adventure.

And yet, as the rolling hills of the Appalachians unfurled before me. As I pulled into camp the first night, I realized I may have underestimated these tree-clad hills. I gave the first few days of my trip not even an ounce of my consideration. The first night of my trip I camped at a place called Fifteen Mile Creek in western Maryland. I picked it only because it popped up on Google Maps and was cheap. I didn’t even realize it was situated on the Chesapeake & Ohio Canal, one of our country’s misguided but no less impressive attempts to build canals for the movement of freight in the early 19th century.

potomac river

That first morning of my trip, I woke up on the banks of the Potomac, mists still hugging its muddy brown waters. I got on my mountain bike and rode down the towpath along the canal as the natural world came to life around me. Riding through the mists, my tires churning up mud left behind from the previous night’s rain, I drifted between contentment and awe. I had no idea this was here. I had no idea it would be so beautiful. 

I was alone on the trail, save for the deer that jumped into the bushes every quarter mile. After half an hour, I stopped along the canal to look around, and I heard a splash in the water. Looking down I saw not one but two beavers, swimming peacefully through the murky water, diving down to fish for their breakfast. 

I’d thought my trip didn’t really start until I got to Colorado. I couldn’t have been more wrong.

The next few days were a constant revelation of my own northern ignorance. Kentucky was a revelation. Rolling grassland with horses dotted on the hillsides. Cities with pockets of artisans and craft breweries and whimsical shops. The best vegan biscuits and gravy I’ve ever had.

Missouri, where I challenged myself to complete an epic 26 mile singletrack ride on my mountain bike, the longest I’d ever done. Camped in the Ozarks, in a forest of scrub oak where the setting sun blazed through the leaves like fire, I felt completely at home. My day on the trail, where the only other person I saw was a trail runner who thanked me for clearing out the cobwebs (and there were many), still stands as one of the best days of my trip so far.

berryman campground

This first leg of the trip surprised me. Throughout my planning and right up until the moment I left (and probably even through Connecticut) I saw these first few days of the trip as something to get through. Something to get out of the way so that I could get to the real trip, out west. So to my surprise I realized that these first few days of the trip have transformed not only my opinion of that slice of America but also of my perspective on this trip.

I wish I’d done a bit more research. I wish I’d known a bit more about the land that I was driving across, and the people and events that shaped it. 

In Kansas, especially, I wish I had prepared more. Driving across eastern Kansas, rolling green hills gave way to vast expanses of agricultural land. This is where so much of the American myth was born, and where the first Americans fought and died and persevered. And I’m woefully ignorant of it. 


Whenever people describe road trips across America to me, they describe the great plains as an obstacle, something to drive through as fast as you can, get it over with, there’s nothing there. The big flat boring area.

But to my eyes, that couldn’t be further from the truth. There are forests and streams, rivers and farmland, open prairie, towns that blend the architecture of the east with the mythology of the old west. Rail lines that stretch for miles. 

It is beautiful here, so open and wide and vast. Kansas is somewhere you slow down, take it in, cross each rise only to have another expanse open up before you, like an ocean of earth.

As I drive across these Great Plains, I’ve been working on focusing on the present, on really living in the moment. Too often, I’m focused on whether I’m doing this trip the right way, or whether I’m living up to other people’s expectations. Even on my mountain bike ride in Missouri, I let my anxiety win out, convincing myself I had to be riding faster, harder, achieving something, when it was an achievement in and of itself just for me to finish the route. Just for me to be there. I got so caught up worrying whether I was riding fast enough, or hard enough, I didn’t savor the experience of being out there, riding one of the oldest trails in the Ozarks.

Am I clinging too tightly to experiences as they happen? Or am I too focused on the future? Why is it so challenging to simply be present?


Is it possible to feel nostalgic for something you’re still experiencing?

Each day I pack up my campsite and head back out on the road, I feel a tug at my heart. This is the end of this part of the trip, I won’t be coming back here. Did I savor it enough? Did I appreciate it enough?

Always looking backwards. Clinging to what was, forgetting what is.

To travel is to be in a constant state of transition. Are we made to live like this?

Has my perspective shifted so much since the last time I did a long term trip? It seems like it has.

It was more challenging for me to settle into this trip than was in the past, when I rode around Cambodia, or walked across Peru. For some reason I didn’t quite feel like I deserved this trip. I think the American mentality has gotten too far under my skin. I’ve given in too much to the idea that in order to be worthy, I have to be productive. I have to be earning money.

Of course, this is a privilege. The amount of financial security, and emotional security I have to allow myself to travel like this, it’s a huge privilege. Is it worth it for me to feel guilty for this? I’m not sure. But I know that I did feel guilty about it. I still do, though that is wearing off. For better or for worst, I have the financial stability to do this, and this is something I crave. And after getting laid off at the very start of covid, of languishing in unemployment and fear for months, and finally rebuilding a freelance career that I’m proud of – I am going to allow myself to enjoy this trip around the country.

fifteen mile creek
fifteen mile creek
chesapeake and ohio canal

Leave a Reply

Your email address will not be published. Required fields are marked *