At the beginning of 2020, I found myself with:

1. five months of unexpected free time
2. a light workload (finishing my new book) that I could accomplish from anywhere with an internet connection
3. sufficient savings to comfortably lead a low-budget lifestyle for half a year
4. the need to reflect on my career, relationships, and other Big Life Stuff

So, I decided to go on an adventure.

How to Not Walk Across the USA

My first plan was to walk and bike across half of the United States on the American Discovery Trail. I would start on the east coast (Delaware) in early February, spend three months walking to St. Louis, and then get a bike and pedal to Denver.

This felt like a sexy plan until I realized that (1) I would need to be hiking 20 miles or pedaling 75 miles essentially every day, and (2) how cold and lonely I’d likely be in those first few months.

The American Discovery Trail excited me because it has the potential to become the “Camino de Santiago” of America, and I had a wonderful experience on the Camino in 2017. Yet today, very few people actually use the American Discovery Trail, so it didn’t offer a community of fellow walkers. And despite the image I like to project (to myself) of being a hearty, independent outdoorsman, I’m fundamentally a very social person. Thus I decided that it would be smarter for me stay closer to more populated areas where I was more likely to encounter friends, family, and nice strangers (e.g., Couchsurfing hosts) along my journey.

That’s when I came up with the second version of my adventure: to venture from the east coast to Denver via exclusively human-powered means. I would still hike (not so much) and bike (a lot more)… but why stop there? Why not roller-skate? Why not scooter? Heck, why not canoe for a stretch? These different methods of transportation would let me get between cities more quickly than walking, which meant more time for socializing.

I got very excited about this idea for about a week. My friend Lea, who I met a year ago when she was crossing New Zealand on an elliptical bike, helped me brainstorm a bunch of different transport methods. I dreamed of bartering one method of transport for the next along my adventure (kind of like the One Red Paperclip guy). But ultimately, this plan felt too complicated and unwieldy. After buying a used pair of strap-on roller-skates on Ebay (which turned out to be very uncomfortable), I realized that it probably made sense to just choose one highly reliable method of transport—biking—and stick with it.

Building the $700 Touring Rig

Long-distance bicycle touring was never something that had called to me in the past, though I’ve always been an enthusiastic short-distance (in-town) bicycler. I also knew very little about fixing bicycles. Yet a little internet research convinced me that, yes, I really could do a bicycle tour with minimal knowledge and resources. So now I just needed a bike.

Fortunately I was spending much of January living in New York City, which has a robust market for used bikes. I quickly found a lightly used touring bike for $400 on Craigslist, complete with disc brakes, rear rack, and a handy handlebar storage pouch.

Immediately after procuring the bike I rode it just a few blocks further south in the East Village and picked up a U-lock—also on Craigslist—for $20. The next day I rode to outer Brooklyn and snagged some snazzy vintage panniers (i.e., saddlebags) for $26 which I attached to my back rack with a few leather belts from Goodwill ($16).

I also bought a number of new items: blinky lights and a security cable ($45), a helmet ($60), maintenance gear and new petals ($45), and riding gloves ($25). Finally, I took a 4-hour bike maintenance course ($65) that taught me how to lube a chain, fix a flat, identify basic shifting and brake issues, and basically not be a complete idiot while biking. All things considered, I spent about $700 to go from having no bike (and little knowledge) to having a tour-ready bike and slightly more knowledge.

Having recently downsized my personal possessions to a week’s worth of clothing, my laptop, and a few books, everything fit easily into the two panniers and small green hiking backpack that I bungee-corded on top of the panniers. I was good to go.

Departure Day, or, A Lesson in the Perils of Freezing Rain and the New Jersey Turnpike

On February 2nd, my Brooklyn sublet ended. I was just getting over the flu, and I’d hardly slept the previous night. Yet it was time to go, so go I did.

The forecast called for clouds with highs in the 40s: not bad, considering what the weather might have been like in early February. My friend Matt (in whose group apartment I’d been living) saw me off with a hug and insisted that I text him when I reach my destination: Princeton, New Jersey, roughly 60 biking miles away.

I made my way over the Brooklyn Bridge, passing a woman in a red leotard who was holding a handstand at the crest of the bridge, before cutting quickly through Manhattan and taking the ferry to Jersey City.

The stretch between Jersey City and Newark was gray, gritty, and occasionally dangerous. At one point, my Google Maps biking directions told me to join a fast-moving highway for a few hundred feet, forcing me to cross an on-ramp and off-ramp for the New Jersey turnpike. There didn’t seem to be any way around this messy interchange, so I went for it, feeling a bit stupid. “This is not how I want to die,” I told myself.

Turning south at Newark, I rode through quiet suburban streets—it was Super Bowl Sunday—until I reached the twenty miles of canal “tow paths” that led into the Princeton area. (These were paths that mules would walk while towing ships up the canals.) I enjoyed the rural bliss for about an hour, after which a cloud descended upon me and dropped sharp bullets of freezing rain. My core stayed warm (thanks to my raincoat) but my hands and feet started going numb. “This is not how I want to die,” I told myself yet again.

I called my friend and host for the night, Alison, a staff member at Princeton Learning Cooperative, to pick me up. She was there in twenty minutes, threw my bike in her car, and made me a big dinner of clam chowder, fresh bread, and salad… but not before I took a long, hot shower. It took quite a while to warm my hands and feet again.

Lesson learned: don’t mess with cold rain.

In fact, why mess with rain at all? I wasn’t on a strict timeline. I decided there and then that I would keep my itinerary highly flexible for the rest of the trip. If rain was on the forecast, I would wait it out somewhere, even if that meant paying extra for lodging. Same with extreme cold. That’s not what I signed up for. No dying for me, thank you very much.

Philly, Baltimore, and DC, Oh My!

After taking a full rest day in Princeton, I rode five surprisingly pleasant hours to Philadelphia that began on picturesque tow paths and segued into flat, well-paved streets with dedicated bike lanes.

In Philadelphia I was warmly greeted by my college friend Martín, his wife Laura, and a feast of veggie tacos. I took a full day to visit Natural Creativity Center, a self-directed learning center I’d wanted to visit for a long time.

With more rain on the forecast, I decided buy an Amtrak ticket to Baltimore. Taking a bike on the Amtrak, I learned, was surprisingly easy and pleasant—you pay $20 extra for the privilege of having them hang your bike up in the luggage car. Well done, Amtrak.

In Baltimore I cried out at the sight of my beautiful, private, self-contained Airbnb room—so pretty, so cheap, and all mine! I spent the weekend reading some new memoirs I picked up at a used bookstore, and working on some of my own memoir writing (as part of an online writing course I was taking). I also reached out to a few interesting looking people on Couchsurfing, as I sometimes do when traveling solo, and got invited over for breakfast with Maya and Max, a couple who recently biked around South Korea with their two young daughters (and a decade ago, crossed the U.S. on a tandem bike). Their story was highly inspiring and made me feel proud to be bike touring.

With rain on the forecast again, I took an inexpensive local train from Baltimore to Washington, DC, and rode to my college friend Stephanie’s apartment, who graciously hosted me on an airbed in her sunroom for 4 nights.

Stephanie’s place was conveniently located on Logan Circle, just a short ride from the White House, National Mall, and other monuments—all of which I toured the next day.

In DC I visited a few people I knew in the education and writing worlds, including Daniel Pink (author of Drive and many other books), Ned Johnson (co-author of The Self-Driven Child), Luba Vangelova, and Bridget, one of my most enthusiastic Patreon supporters.

A Busted Pannier and a Fusion Dance Weekend

On February 16th, while riding south out of DC, I experienced my first (and only) bike disaster: one of the metal clips that secured my vintage panniers to the rear rack snapped off, leaving me with a pathetically limping saddlebag that would soon detach completely.

Fortunately—and really, this was beyond good fortune—I was only blocks away from a bike shop when this happened. I purchased a glossy new pair of highly reliable Ortlieb panniers. Thank you, Conte’s Bike Shop of Alexandria, Virginia!

I pressed on to Woodbridge, Virginia, where I moved into an Airbnb room and immediately turned my attention to Unity Fusion, a weekend-long fusion dance festival.

I’ve been a fan of fusion dancing since I attended my first festival in 2016, and this event didn’t disappoint—bringing together fun, talented, and open-minded dancers who care more about the feeling of connection than looking good or performing fancy moves. (If you’re wondering what fusion dance is, read this brief description written by my friend Flouer, or watch this video.)

Between the back-to-back workshops, dances, and conversations, I had a wonderful three nights and two days. I also got to hang out with my friend Catina from the Embark Center (a nearby self-directed learning center), and I enjoyed a magical connection with one of the dance instructors, Krysta.

Cold Hills and Warmshowers

The morning after Unity Fusion, I enjoyed a warm, pleasant ride to Fredericksburg, Virginia, which lies halfway between the former Union and Confederate capitals of Washington, DC, and Richmond, Virginia. I passed a number of Civil War sites along the way and received my first friendly gestures from strangers on rural roads. At the University of William & Mary in downtown Fredericksburg, I sat on a large white lawn chair in the middle of a sprawling college green, soaking up the sun, surrounded by milling college students.

My destination for the night was a stranger’s house: my first-ever Warmshowers host. Warmshowers is like Couchsurfing, but just for bicycle tourists. I contacted my hosts, Bruce and Vikki, a few days ahead of time and requested permission to stay the night; they graciously accepted.

Upon arriving Vikki greeted me warmly, showed me my private room and bathroom (which formerly belong to her kids), and introduced me to the three cats they had rescued from Bruce’s work site. One of them really loved sleeping on top of plastic bags. Adorable.

When Bruce returned from work, we three enjoyed a huge spaghetti dinner, and Bruce talked my ear off about the cross-country bike trips he’d led with large groups of Eagle Scouts. The next morning Vicki made me ham and eggs and sent me off with chocolate chip cookies and a Honeycrisp apple. “Thanks mom!” I said as I walked out the front door.

My next day’s ride was cold and hilly, and I developed a little mantra that I must have repeated at least a hundred times:

Less chilly hilly
More flat and warm

I also spent some time biking along Highway 1, where there wasn’t much of a shoulder. This prompted another mantra:

Riding down the Highway One
Feeling just a little dumb

At 11am I shoveled chips and enchiladas into my mouth at a tiny Mexican restaurant. That fueled my next 3 hours of riding to Richmond, where I camped out at a hipster coffee shop until my Couchsurfing host, Liz, returned from work.

Liz was an avid cyclist who had recently suffered a concussion after striking a car. Her ex-boyfriend of 8 years, Bobby, who had ridden across the US a few years ago, joined us and cooked up a big vegan stir-fry dinner. Bobby and Liz had been dating since early college and living in the apartment where Liz was hosting me, but now they were living separately and dating other people. I was impressed by how much effort they put into staying friends after their (still fresh) breakup.

The next morning I biked through downtown Virginia to my friend Grey’s apartment, where spent the next two nights. I met Grey at a Virginia homeschooling conference in 2015 and was immediately impressed by her love for travel, wit, and confidence. We explored the city together, chatted about relationships, and played some highly competitive card games. I celebrated the completion of the Kickstarter for my new book, which ultimately reached 140% of its goal.

Although I had enjoyed a relatively mild winter thus far, I was fully aware that it was still February, and I was still in the hilly/chilly mid-Atlantic. Now felt like a good time to zip ahead to the warmer and flatter lands of the south. So I booked myself an Amtrak ticket from Richmond to Charleston, South Carolina, skipping virtually all of the Carolinas in the process. My “bike trip” was now officially a “bike and train” trip. Number of regrets: zero.

Holed up in the Holy City

In Charleston I couchsurfed with Shawnda for two nights, a fun and generous woman who owned a cleaning business and enthusiastically told me why turning 40 is the best thing ever (because you accept big parts of who you are, and you stop apologizing for them). I slept on the sectional sofa in her stylish 1-bedroom apartment.

With more rain on the horizon, I booked myself a few extra nights at a local hostel. Contemplating how I might spend my time in Charleston, I explained to Shawnda how I had just finished a Kickstarter campaign, and now I needed to create the audiobook, and maybe I could do that while I’m stuck here in Charleston, but the one local recording studio I found was too busy and too expensive…

“Hold on,” Shawnda told me. “I’ve got a friend in town who might be able to help you.”

She gave me the phone number for Clay, a musician and prolific Couchsurfing host, who immediately responded to my text message. He was too busy to help me out, but he connected me to his other friend, Corey, another local musician with a home recording studio.

I texted Corey, and just hours later, I found myself at his apartment doing a test recording. Over the next two days we proceeded to record the entire unabridged audiobook of Why Are You Still Sending Your Kids to School? in two marathon-length recording sessions. Boom!

The audiobook was by far the most time-consuming part of my Kickstarter obligations, and it felt amazing to have completed it.

The Land of the Alligator

From Charleston I embarked on what would become my longest day yet: 80 miles, much of it with a headwind, ending in Beaufort, South Carolina.

While riding along Highway 17 I enjoyed virtually no shoulder, which felt harrowing, but the vehicles always gave me lots of space when they passed. (The worst offenders? Schoolbuses.) A lunch of fried fish and shrimp at a restaurant on the side of the highway replenished my tired legs. I smiled when an old white man walked into the restaurant, saw old black man he recognized, and the two started loudly reminiscing about their “coon huntin” days together.

On the second half of my ride I passed a young-looking guy with a baby stroller who asked “You traveling?” as I glided past. I quickly responded that I was riding to Colorado, he yelled something like “I’m walking to DC!”—but I couldn’t be sure, because I didn’t stop for him. He wanted to talk; I wanted to get to my destination. I felt a bit bad about that.

In Beaufort I overnighted with Scott and Sue, Warmshowers hosts who homeschooled all their (now grown and flown) kids in a traditional Christian fashion. They fed me a huge meal of prime rib, mashed potatoes, mac and cheese, green beans, and salad. Still famished from my long ride, I polished off three sleeves of miniature Snickers, Butterfingers, and Baby Ruth for my personal dessert. Their dog Buddy, whom they affectionately referred to as their “canine hunting school dropout,” kept me company.

In the morning Scott made me eggs, Sue gave me fresh-baked cookies, and off I rode to Hilton Head Island, Georgia, the iconic golf and beach resort destination. The weather was sunny and warm, and I felt like I’d finally arrived in “the south”—a fact that was confirmed when I encountered my first-ever “Beware of Alligators” sign at a public park.

That night I stayed with Van from Couchsurfing, a warm-hearted emergency room doctor with a huge, beautiful home in a gated community, where he lived with his wife, mother, and mother’s live-in caretakers. Van and his wife had previously enjoyed hosting international exchange students, which prompted them to later begin hosting Couchsurfers. Originally from Ohio, Van told me that one winter he didn’t see the sun for an entire month—that’s when he knew it was time to move south.

I ended up spending some nice extra days on Hilton Head Island with a friend who came down to visit me. During that time I researched potential biking routes across rural Georgia and the Florida panhandle—none of which inspired me—and ended up booking a one-way rental car from Hilton Head to the Florida gulf coast, which felt like a more interesting (and accommodating) place to spend my time biking.

I picked up the rental car at Hilton Head Airport, and after a quick stop in Savannah to have lunch with the mother of one of my former students (who also interviewed me for her local radio show), I sped southwest from the Atlantic to the Gulf of Mexico, ready to tackle the longest stretch of my ever-evolving bike tour.

From Panama City to New Orleans

In Panama City, Florida, I crashed in the backyard RV of my friend Joey, a two-time former Unschool Adventures participant, who was unfortunately out of town. Despite my years of nomadism, I’d never slept in an RV before—it was surprisingly nice.

The next day was the most enjoyable day of biking yet: a long, flat, ride with the Gulf of Mexico on my left and an all-day tailwind. I stopped twice for donuts—many donut shops lined this stretch of Spring Break / Family Vacation-land—and ate two donuts at each stop. Number of regrets: still zero.

That night I couchsurfed with Nick, an incredibly friendly 24-year-old who had hitchhiked 1,500 miles across the northern USA and now worked as weapons analyst (modeling air-to-air missiles) for a local military base. Nick was a top candidate for the Air Force flight school until he was unexpectedly disqualified due to a history of kidney stones. A copy of Ram Dass’ Be Here Now sat on his desk.

With more friendly tailwinds the next day, I cruised at top speed on a nicely paved road surrounded by the white sands of Santa Rosa Island, part of Gulf Islands National Seashore.

After a harrowing bridge crossing into Pensacola (the dedicated biker/pedestrian lane was out of commission), I finished my day at the residence of Warmshowers hosts Keith and Birdie, who ended up in Pensacola after floating their houseboat all the way down from Minneapolis.

Keith hated school as a kid, studied Physics and Math in college, never graduated, taught himself programming, and is now designing his own massive multiplayer online game. He inherited his dog, Mr. Whoopers, from his brother who died in a car crash. Every morning he prepares eggs over easy for Mr. Whoopers, who also gets a few slices of sharp white cheddar cheese.

The next day brought another pleasant ride—to Gulf Shores, Alabama—and another interesting host: Ramune, a 26-year-old woman originally from Lithuania, who met her now-husband on Couchsurfing when she was age 23, hitchhiking from Florida to Mexico. She only intended to stay with Robert for 3 days and ended up staying for 2 months. Fast-forward: Ramune and Robert are now married with two lovely kids. What a wild world!

Ramune did seem rather isolated and lonely as a stay-at-home mom, unfortunately, and was quite happy to have to my company. She and Robert and I shared a lovely dinner, and I slept on the super-comfy couch in their youngest child’s room (who they had sleep in the living room).

I had been doing 60-70 miles days along the gulf coast thus far; now it was time for my longest day ever, 90 miles to Biloxi, Mississippi. Departing at sunrise, I made my way to the Fort Morgan – Dauphin Island ferry (which saved me the trouble of biking through Mobile, Alabama) and then pedaled along rural Mississippi roads for a long, long time.

Today was the one and only day that I encountered other long-distance bikers along my journey: Nicholas from Germany and Sam from Massachusetts. They both had camping gear and were much dirtier than my indulgent, bed-loving self.

In Biloxi I couchsurfed with an interesting young family who made me think of the movie Captain Fantastic. Upon arriving the parents weren’t but home, but I was immediately invited to go out to a brewery with a few friends of the family. One of those friends was Kenny, a diehard hitchhiker and minimalist who recently published a book about his adventures and was now plotting a brewery-based book tour. Kenny also sews his own ultralight backpacks that transform into bivy sacks.

Later that evening I met the parents, Christian and Skellie. Christian managed a successful local tattoo shop and loved debating grand theories of philosophy and human nature. I joined him in debate for a solid hour that evening, but then things started to get heated and I decided to retire for the night. He left me a sweet hand-written note the next morning asking if I’d stay another night, but I already had plans to press on to my final destination: New Orleans. I took off just after sunrise the next morning.

NOLA and the unexpected end of my voyage

The final push into New Orleans was a sunny 86 miles with multiple bayou crossings. I lunched on a catfish sandwich at Turtle Landing, a tiny pub packed with construction workers, and rolled into NOLA (New Orleans, Louisiana) feeling hot and salty. I crashed with another Warmshowers host, John, a cheery 25-year-old Habitat for Humanity volunteer who cooked me Chakchouka. I returned the favor by providing beer and ice cream.

My plan was to spend a few days at a New Orleans hostel, visit my old friend Cameron, and then press on to Texas—but by now it was mid-March, and the public awareness of Coronavirus was turning serious. I did end up staying in the hostel for five nights—and by the fifth night, I was the only guest remaining. I felt more fortunate than my 29-year-old hostel roommate, Joaquin, an Argentine tourist who couldn’t find a flight back to Argentina.

I did end up seeing Cameron a number of times, but he was slightly under the weather, so we stayed six feet apart the whole time. Cameron and I have gone on a number of backpacking trips and Unschool Adventures programs together, and it was wonderful catching up with him.

By March 18th, it was clearly apparent that my trip had come to an end. The life of constant traveler was becoming increasingly unreasonable, and Couchsurfing and Warmshowers hosts were drying up like puddles in the sun.

I took the Amtrak from NOLA to Houston, crashed with a friend from New Zealand for an evening, and then rented a car for a day to get to Austin, where I had a few friends and family members. I spent 10 nights an Airbnb there before deciding that the safest thing to do was simply rent another car and drive straight to my final destination: Paonia, Colorado, where my friends Dev and Marian had a large property where they would happily host me for April and May.

That’s what I did, and Paonia is where I write you from today. Thus ended my bike trip.