To Know the Place Again, for the First Time: Two Months on the Road in the US

just outside the Wind River Reservation in Wyoming

This summer I embarked on the most ambitious road trip of my life. I had a car the entire time and I interspersed places I had long wanted to see among business and personal appointments. Despite having traveled a fair bit in my life and giving myself (what I thought were) appropriate rest days, the journey ended up being one of the most challenging travel itineraries I’ve ever pulled off.

I say “challenging” with a fair amount of joy, for we should take pleasure in our exertions, especially if they bring us lasting satisfaction, which this trip did in so many ways.

The trip began, fittingly enough, in Dallas, Texas. My family first moved to Dallas from Singapore in 1988. We had relatives living there at the time (who live there still) and it was here that my first impressions of America formed. This long layover allowed me to visit with some of my relatives, catch up with friends who live in the area, and even see one of my Writerly clients that happens to headquarter out of Dallas.

While there is much in my life to make Dallas dear to me, in regards to urban planning it represents some of the worst of the dehumanizing automobile-driven sprawl development perfected by post-war American “urban planners” (mostly comprised of car dealers, brutal architects, and unimaginative government officials). In this way Dallas can be a bewildering web of freeways with thieving tolls that is ever expanding outward with no real plan but OUT.

As an aside, should you have a desire to stop over in a hub city of an airline, you can create a mini-trip like this for yourself. The airline will allow you to take a very long layover (sometimes overnight) at no additional cost. It will also give you a bit of “normalization time” — a chance to breathe non-airport air, feel the sunshine (or cold, as it may be), and walk around. It may make the circadian adjustments easier for you.

This strategy also works with Singapore Airlines, I recently discovered.

After eight hours in Dallas it was onward to Kansas City where I would stay for a week. For a long term car rental — anything over a week — it’s usually worth the trouble to rent from a non-airport location. Airport locations can charge a higher daily rate. I’d never rented a car for this long, though, and it was quoted at roughly $1800 USD, or $900/month since I would be in the US for eight weeks. This didn’t include insurance (which I didn’t get, trusting to that provided by my credit card) nor gas (which I’ll come to later on). This was the lowest rate I could find, and it was with Hertz, with whom I rent almost 100% of the time in the US, because they always seem to have the lowest rates in the Kansas City area. The price felt “high,” but what did I know, really? I’d never rented a car for that long before, and as I reflected on it more, I realized their exposure was significant: someone driving a car for two months might necessarily be a greater risk than someone driving for two days.

I divided the $900 across thirty days and came up with a $30 “daily transportation charge.” Now, if we think about this in terms of a city metro, it’s unreasonably high. But if you think of it as on-call private transportation, the cost is suddenly quite reasonable. If you were to take others on the road trip with you and split the cost, it would become increasingly so.

They didn’t have the size I booked so I got upgraded (a strategy that works some of the time), but after a month of driving a gas-guzzling Chevy Malibu, I took a swap (you have to report your mileage periodically on what Hertz calls a “multi-month rental” and you can either do an oil change and be reimbursed or swap out the vehicle) as a chance to get into one of my favorite rental vehicles, the fuel-efficient, roomy, and very drivable Hyundai Sonata.

Gas prices on the trip across 20 different states were as low as $2.33/gallon and as high as $3.40/gallon so the difference between these could be construed as $2.86 (too many fillups for me to do an exact average), which for my metric friends is roughly 67 cents per litre. What America desperately lacks in infrastructure (no trains, buses, or budget airlines that provide reliable nationwide service) it more than makes up for in offering very low cost private transportation costs. I drove a total of 12,253 miles, or 19,719 kilometers, at a total cost of $1008 USD (921,27€) or $16.80 USD/15,35€ per day. So that meant my total transportation costs (car + petrol) for two months in the US was roughly $46.80 USD/42,62€ per day. If you add in some occasional expensive inner city parking and hateful tolls from the thieving state of Illinois, $50 USD/day would still be a conservative transportation estimate for a trip of such duration and mileage.

The fuel costs in France are more than double what I’ve listed above and the tolls are eye-watering. Paris to Nice alone costs 160€ in tolls. Ask me again why I’ve driven in Europe a total of thirty days in six years.

It was an interesting point of reflection that my strict Asian mother who had, in my youth, frowned on sleepovers and limited video games during the school year to 30 continuous minutes on the weekend after homework was completed, registered no significant protest at my driving from California to New Hampshire, a distance of 3000 miles (4800 km), never having driven more than 2–4 hours by myself before. How dazzled I was on that first long road trip, my freshman year of college, and with what wiser eyes I saw some of the same sights, and many new ones, on this trip.

How could I possibly have driven so much? To be honest, I’m still a bit surprised myself. I certainly didn’t begin the trip in that way, spending a week in Kansas City attending to personal business and seeing friends, followed by another week in St. Mary’s, Kansas, spent with nieces and nephews and, for the first time in many years, cutting my mother’s lawn.

This was one of the most luxurious parts of the trip for me. I often share that when you live in a different country from our family, it’s a good idea to visit “off season,” meaning, not during a particular holiday. You don’t have to share your family with their in-laws and other obligations, moreover you have the chance to simply observe and chat with them as they go about their daily tasks. I was able to get lunches with my brothers-in-law and see their workplaces, and take my sisters and mother for one-on-one weekday lunches. No kids — just a chance for a quiet catch-up.

As for the nieces and nephews, I got to carry on the legacy of my late father’s “secret meetings.” More often than not this was simply a chance for us to go out of the house for an ice cream, but I adapted it for my nieces and nephews, dividing them into the 6-and-older and the 5-and-under groups, taking them to different places for a treat and for some time together. The “secret” was that we didn’t have to tell anyone where we went, before or after, but the chattiest (worst secret keepers) made sure it wasn’t secret for long. :-)

Long drives, apart from giving you the opportunity to binge on podcasts and audiobooks, offer you plenty of time to ponder, and at the time of my trip I was approaching the first anniversary of my father’s death. I found some helpful reflections in this article, which reminded me, above all, that grieving exists outside of time as we normally conceive of it. My father had always told me that he never “got over” the death of his parents. They were always missed. I pondered that while he was alive. I know it to be true now that he is gone. I still miss him very much, and I hope I always will.

It was at these meetings that I announced my first summer challenge to the kids, to be performed on my return visit in July. The girls could do one minute of hula hoop or two minutes of jump rope; the boys could do two minutes of jump rope or ten dead hang pull ups. While protests were registered by both children and their parents as to the ability to achieve these goals, I reminded everyone that yes, they were capable, and anyway, it was my contest, my rules.

St. Mary’s, where most of my family now lives, hosted my paternal grandfather for boarding school, as well as two of my siblings for boarding school nearly 80 years later. I spent a year in the college there myself, in total living for about two years in a town of 3000 people. There are still friends in and around town that I catch up with, and it’s been nice to see the town slowly develop over the last twenty years.

So, after the two weeks of seeing family and friends, I headed off on my first adventure: a road trip to Mount Rushmore, which would also be my first visit to South Dakota. Long drives are tiring when you are unused to them, and after 714 miles (1149 km) I arrived fairly tired to Rapid City, South Dakota, having spent eleven hours on the road. Perspective for my European friends? That’s the distance from Paris to Prague.

Mount Rushmore has a carnivalesque atmosphere. It’s full of families with kids and can be as long or short of a visit as you want. Fans of Hitchcock’s North by Northwest will inevitably smile at the movie’s climactic finish across this edifice, but it really is an impressive bit of art and engineering. The trail is well marked and there are plenty of ranger talks or exhibits should you wish to learn more, but even the short 30 minutes leisurely loop trail will give you some impressive views and perspectives.

Not too far from Mt. Rushmore is Crazy Horse, originally conceived of by Standing Bear as a Native American complement to Mt. Rushmore. While there is the faint outline of a monument to this legendary warrior, the family in charge of the memorial refuses to take federal funds and seems committed to a Sagrada Familiaesque timeline (i.e. who knows when it will be finished?). That said, the venue itself is a treasure trove of Native American history, with a museum, a college, and cultural center, among other things, on the sprawling property. It’s maybe a 45 minute drive from Mt. Rushmore, through some lovely rolling hills.

But, by far my favorite destination on this part of the journey was Devil’s Tower National Monument in Wyoming. A large and spectacular igneous rock formation with no definitive geological explanation, it conveys a quiet peacefulness in contrast to the circus at Mt. Rushmore, and offers various trails around the monument itself, which you can choose from depending on your time and desire to hike. Everything about Devil’s Tower (known as Bear Lodge to the Lakota people) is serene, peaceful, and inspiring.

I then had a chance to drive through the state of Wyoming and passed through the impressive Grand Teton National Park, where I spotted my first bison of the trip. I knew I would be back later in the summer so I only made a couple stops while enjoying one of the most scenic drives in the country.

I would end up in Sundance, Utah. I spent a guy’s weekend with some friends I had been meaning to get together for some time. We grilled, kayaked, hiked, and just relaxed. My very first business mentor introduced me to Sundance in the mid 2000s, and I’ve been bringing friends there ever since, though this was my first visit since moving out of the US in 2013.

After dropping my friends at the airport I drove south to Moab, Utah, just outside Arches National Park. It was high summer, so the weather was hot, but as long as you bring enough sunscreen and water you’ll survive. Arches, with its magnificent 36 mile loop of vast, endless vistas, is something all should experience and enjoy, whatever the time of year. You’re reminded almost continuously of the length of time in God’s creation, and our very small, but providentially ordained, role in it. I was reminded of the words of a favorite sermon: “life is short, eternity is long.”

I made my way back from Arches to join my family for the July 4th holiday. My sister and her child flew in from California to join us for our first family pictures since her wedding. I think they turned out well and it’s always a pleasure for me to have pictures I can look at when I’m on the other side of the water. Almost all of us were together, though a death in his family understandably kept one brother-in-law from joining us. Fireworks and sparklers were lit, hamburgers and hot dogs were enjoyed, and I brought a couple Berry Chantilly cakes from Whole Foods, which are a regular contribution I make to large family meals (if you haven’t tried these, you should).

What do you love about America, I’m often asked. Diners, in particular, Waffle House. There’s no rush. They are open at all hours and hold no judgment against your desire for a philly cheese hash brown bowl with jalapenos at 10pm. That late night unhurried comfort food is a luxury we simply don’t have in the same way in Europe, and that’s okay. I can savor it all the more when I’m stateside.

The kids did their physical challenges, and it was fun to see it play out: Lucy, the brainiac who said she “couldn’t possibly” do a physical challenge…until she did; my nephew Dante, who had been working on his pullups since my visit the previous month and hit the goal of ten, unlike his overconfident older cousin Matthew, who like the hare in Aesop’s story of the Tortoise and the Hare, trusted too much in his own abilities and fell short. The younger boys, who couldn’t yet do pull-ups, were challenged to hold on to the bar without assistance for two minutes, which they did! It was a great reminder to everyone that the only thing holding us back from our goals is our work ethic and willpower.

It was nice for our family to be all together. We live far apart now so moments like these are treasured (and have to be planned in advance). I prepared to leave for my next set of adventures and left a more complicated mental challenge for my August visit: memorizing the names of all 50 states.

I drove to Illinois, to partake in a few days of the Fleming Foundation’s Annual Summer Symposium. This year’s theme was Shakespeare and the history of England. Dr. Fleming challenged some of us to recite some lines from the Bard and I reached back to a previous obsession with Hamlet which bore as one of its fruits a memorized monologue from the end of Act III.

While some of my writings and work for the Foundation require a (free) login to access, some of them were originally written for Front Porch Republic.

I next arrived for some work at St. Gertrude the Great in Ohio. I would record some episodes for next season of Restoration Radio. Before too long I was on my way to North Dakota, with an overnight stay in Minneapolis. This was the longest stretch of driving on this trip, over 1400 miles (2250 km) across two days. When I crossed into North Dakota, below endless clouds, I had at long last been to all 48 of the continental United States.

After so much driving a pause was warranted, and I spent a day exploring the little known but beautiful Theodore Roosevelt National Park, which actually has three segments — I chose to spend the day in the Southern Unit. Bison, wild horses, prairie dogs: all were wandering around this beautiful and underappreciated park.

In a certain way, this landscape that made Roosevelt (in his own words) a decided conservationist is responsible for all the National Parks Roosevelt created and fostered momentum for, which would be realized under future presidents.

After resting a couple days in the far west of North Dakota, I pressed on to Little Bighorn National Battlefield, which is very well presented by the National Park Service, with wall-to-wall ranger talks (many of the Rangers are Native Americans), informative trail markers and grave stones, and a free audioguide.

Four hundred miles later, on the other side of Montana lay Missoula, my next stop. I got to know the town a bit as well as drive up to the Lolo Pass, famous as part of Lewis and Clark’s journey but known also for the retreat of Chief Joseph. It straddles the Pacific and Mountain time zones so it’s an hour earlier when you get there but an hour later when you leave.

Missoula natives will be the first to tell you that the town has changed dramatically in the last 5–10 years. Present-day Missoula reminds me of Austin or Portland in the early 2000s or Nashville ten years ago, before these towns got discovered, crowded, and overpriced. I suspect Missoula will not undergo something similar for reasons of weather (its non-summer climate is too extreme for most) and remoteness (it’s not convenient/inexpensive to get to by airplane). I’m sure that status quo is fine for most Missoulans, who are doing fine without you, thank you very much.

After a couple days of rest in Missoula I pressed on another 500 miles (800 km) to Skykomish, which is located inside the Stevens Pass, not far from Seattle. The Pacific Northwest is truly beautiful, but I wasn’t in Skykomish for sightseeing alone. Some business partners and I had rented a cabin for a week in order to shoot six courses on starting a business, meetup groups, becoming an airbnb super host, travel, and long-term and entrepreneurial visas for France. One of my coaching clients had inspired me to bottle some of my knowledge and while the recording part was certainly a challenge, much more work and learning lay ahead, as Dan Fox went into editing mode to piece all of the recordings together in a coherent manner. We also added the right descriptions to turn browsers into buyers and we definitely came away with a true appreciation of how challenging putting together a single course is, much less six!

We did manage to take a break from filming long enough to go to Vancouver and Seattle for the weekend. The natural beauty around Vancouver is as astonishing as the homelessness is shocking. Entire city parks have become homeless encampments and entire neighborhoods are punctuated by homeless encampments on the sidewalks. A city that lives like this is a city that has, in a way, given up on itself.

Grouse Mountain provides spectacular views over the Vancouver region and on a clear day the views are endless. There are grizzly bears and birds of prey up there. Don’t miss it.

Before we crossed back across the border we stopped in the picturesque beach town of White Rock for part of a business design fiesta hosted by my colleague Dan Johnston. The people he had gathered for a weekend of designing businesses to launch were engaging and lovely, and it was a perfect end to a long day in Canada.

I didn’t get as much of a look at Seattle, as I spent most of our day there eating [note: do not miss June Baby if you, like me, love Southern Cuisine (but definitely skip the Wandering Goose) and if you are a burger lover, stop by Lil’ Woody’s; it’s underpriced goodness!]

Many friends know me to be a breakfast hound. When I do research in a city before arriving and I see the same place consistently mentioned that can mean it’s either genuinely good or overly hyped. I can tell you that in case of Medina Cafe it’s the former. Get there 30 minutes before it opens at 9 if you want to make the first seating, or get there at 9 to be on the list for the first “turn” at 10. They will take your name and you can take a walk in the meantime. Don’t worry, they won’t push you out: Vancouverites, like many Canadians, don’t linger at any meal, much less breakfast, but the staff make you feel welcome and you can stay as long as you’d like.

With the biggest project of the trip behind me, it was time to relax a bit and I headed south into Oregon to taste some of the renowned Willamette Valley varietals and blends. I also revisited some of my childhood by going to the end of the Oregon Trail, a goal I so rarely achieved in the computer game of my youth.

Long before I had the joy of properly spelling it consistently, I had fallen in love with the Korean dish of bibimbap. As another testament to “you never know when you’ll come across it” some of the best bibimap I’ve sampled in my life was at Happy Bibimbap House in Salem, Oregon. Don’t be (or do be!) distracted by the Korean posters/art/photos that are crammed ino the establishment or the “we need to have lots of other dishes that might interest Americans” choices on the menu. Order the classic bibimbap and thank me later.

Oregon wine country was an interesting discovery. Rather than giving small pours free, or for a marginal cost that is 100% applicable to the wine purchases (which has been my experience in France, Italy, Australia, New Zealand, and even South Dakota), they are going to charge you around $20 USD for a flight of 3–4 wines, all with pours that are double or triple the tasting portion you might have had elsewhere, and this cost is not directly applicable to a purchase of a bottle. While I did get to have some great conversations about wine with some of the staff, it’s clear that important revenue streams here are from memberships to the specific vineyard (which is a commitment to purchasing a certain number of bottles per year, sometimes with free shipping or access to exclusive runs as incentives) and special events like themed and paired wine dinners. My usual ambition of visiting 3–4 cellar doors on a given day was thus blunted and I was compelled to stop after visiting Ponzi and Argyle, though those were still a great exposure to what’s on offer in Oregon.

The historic Oregon Trail had a very steep conclusion for hopeful settlers: descent with their wagons into the Columbia River Gorge. As I thought through all the parts of the trail that I had seen on this and previous drives, I wondered what kept people moving forward when they could so easily stop at any number of picturesque stops near rivers, mountains, and forests. Sure, it afforded none of the “protection” found near a large settlement as they could find in Salem, but so many died and drowned along the way that they may have been just as safe trying their luck in the open country as trying to make it to Oregon in one go. I thought, on reflection, that it wasn’t that surprising that I almost never made it to Oregon in the computer game of my youth. Many in real life didn’t either.

The longest drives were behind me, and now the drives seemed easier, since I had been on the road for six weeks. I stopped at the wonderful Craters of the Moon National Park in the middle of Idaho and got to explore lava tubes, which are hollow caves in which lava once flowed and formed a fascinating underground topography.

Unwittingly, I was preparing for my next stop by making this one, as this Park was the site of the last eruption of the supervolcano which, over time, had moved under Yellowstone, where it presently lies, biding its time until its next eruption. The landscape at Craters is unlike anything I’ve ever seen, though those who have lived in and around volcanic areas would see much that they would recognize.

After arriving in St. Anthony, Idaho, I had a brief rest before embarking on the National Park highlight of my entire visit stateside: two days in Yellowstone and a day in Grand Teton. Both parks together could easily take a week of your time if you made the time to see them. They are extraordinary nature preserves open to the public: bison, elk, moose, bears, wolves, beavers, all beside rivers, lakes, waterfalls, canyons, mountains, geysers, and hot springs and bubbling mud. It’s a fairy land, and available for the cost of a song — an annual National Parks pass costs only $80 USD, which covers everyone in the vehicle you are driving. If you want to stay inside Yellowstone, your best bet is to book a year in advance. There are lodgings for every budget, but if you, like me, wait until two months before your visit, all you will see is sporadic availability in which hope is your strategy.

I have never been to Alaska, but that doesn’t really blunt, just contextualizes, my assertion that the Yellowstone/Grand Teton ecosystem cannot be recommended highly enough. You will carry the signs, sounds, and smells of your visit for a long time afterwards.

Full of the refreshment that only nature can grant, I next stopped at Wyoming Catholic College to meet the President of the school to discuss some future projects but also to enjoy its picturesque setting in Lander, on the edge of the Wind River reservation.

While I don’t entirely endorse the “Great Books” argument as articulated by Mortimer Adler and others (I’m more a disciple of Dr. John Senior’s “1000 Good Books”) the matching of such a curriculum to the rugged Wyoming landscape would be utterly irresistible to me if I were 18 again.

The weekend after saw me first in Boulder, then Denver, which gave me time to see friends in the surrounding areas. I also got to try some Colorado cheese and charcuterie (the local Colorado Blue sold by St. Kilian’s is particularly fine: one of the best blue cheeses I’ve ever tried on any continent).

The final few days flew by. I drove through Colorado and Kansas to arrive back into St. Mary’s, with some stops along the way to see friends. My nieces and nephews recited the states, much to my delight, and they were promised a bigger challenge (and reward) when I returned next year. I returned to Kansas City, turned in my car, took another long layover in Dallas, then headed home to Paris.

There were so many things this trip made me grateful for. In the first place, I remember God, and the marvelous details which light up creation, which were so on display for me during this trip, which occurred in some of the finest summer weather I have ever known in my short life.

I was grateful to have my family, to be able to see them all together and to have the time to catch up with them and have some special time with my nieces and nephews.

I was grateful to my professional mentors and colleagues, who punctuated the sightseeing with heads-down serious work, when we weren’t busy having a laugh (or eating pancake ice cream).

Finally, I was grateful to have so many friends, old and new, who welcomed me cordially at every stage of the trip. They helped me to see the country I lived in for 25 years through newer, wiser eyes, so that I could know it again, for the first time.

Singaporean-born American in Paris. I connect, educate, and build, AMDG. Follow my adventures at

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