American History Bike Tour


After nearly a decade in NYC and set on applying to business school in late 2015 — I’ve since been accepted to Duke Fuqua — I took a huge gamble and left my job in the summer of 2015, moved out of NYC, and tackled a dream I knew would be a once in a lifetime adventure.


Some highlights of the trip include: camping at Gettysburg on July 4th, sleeping on the floor of a bike shop, large meals (12 eggs for lunch, 24 wings for dinner), a child remarking on how bad I smell in line at Burger King, spending a rainy night in a Virginia farmhouse with a family who invited the neighbors over for poetry and guitars in celebration of hosting me, sleeping in a church gym in eastern Kentucky, turning 30 years old as I crossed the continental divide, and following the Grant vs. Lee duel on my bike through Richmond, Petersburg, Lee’s retreat, and the surrender at Appomattox, which became my favorite site because of what it represents: grace in victory, dignity in defeat.

A map showing where I slept each night along my route, along with a list of American history sites I pedaled through is below.


    I rode a touring bike, a brand new Surly Long Haul Trucker, which I named “Big Medicine” after the .405 Winchester rifle Theodore Roosevelt brought on his post-presidency life adventure in East Africa. The detailed bike specs, and list of things I carried and places I visited are below (more for my own record).

    But essentially touring bikes have a number of features that help with consistent, daily, long-distance pedaling: a steel frame (makes it a tank, and a much softer ride than aluminum), thicker-walled frame and tub ends at stress points (so it can hold more weight), versatile drive train/crankset/cassette (increased gear range and torque ratios), a higher, more comfortable front end with drop handlebars, a skinny saddle (minimal surface contact is important), cantilever brakes (about as strong as disks, but designed for easy brake pad swapping), stronger wheels (36 spokes!), and bar-end friction shifting (less likely to break, can change from smallest to largest gear in one swoop).





    Route 66 Certificate of Completion

    4 thoughts on “American History Bike Tour

    1. I was really impressed along with your style, analysis and how you created it all simple to adhere to. My friend and I have been searching for this info and I told a colleague about it as well. It’s fantastic to see when somebody takes as substantially pride in their perform as you do. I hope you continue to work on new projects. Thank you once again and keep up the superior work.

    2. So cool! I would love to do something like this…although my dream is to travel down the west coast from Vancouver to San Diego. Those long haul truckers are sturdy but so heavy…I can tell you were trying to cut weight wherever you could. How many flat tires did you get along the way?
      Tessa (from Bucknell)

      • Tessa! How’ve you been?!

        I love my Long Haul Trucker, and it is heavy, but ironically it feels like it rides more smoothly when it’s fully loaded up with even more weight. On the days when I’d lock my gear at the campsite or in a motel and rode the bike naked it felt surprisingly more rigid.

        11 flat tires, but that’s deceptively high. 3 or 4 of those flats were because my back tire’s tread wore out and I tried patching in every way possible to try to get to a bike store to replace the tire. And I had one day where some kind of staple was stuck in the inner lining of the tire, so I blew out like 5 tubes that day. Except for those two occasions, there were very few flats!

        Let me know if you end up doing Vancouver to San Diego! I have lots of tips/feelings about what I would have done differently going into my first tour like this.

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