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Riding the Rails to Chicago — My Own Version of Planes, Trains and Automobiles

A few weeks ago, our bud Matt Kovalakides (aka Matt Koval on YouTube) did an online short entitled “The Baloney Train” (also embedded below) about a trip he took several years ago cross country on Amtrak.

His friends told him that all these hot European women would be on the train, ya know … because everyone travels by train in Europe. Sadly, this is America and well, watch the video and you’ll hear Matt’s sad tale of 3,000 miles in Amtrak coach.

So it just so happened I was coordinating Matt’s travel to come do some video work at the 2008 FOLIO: Show in Chicago, which takes place this week from Monday through Wednesday. (For the record, It’s the cool hip conference for magazine and publishing industry professionals who want to learn, share and be inspired).

Needless to say Matt wasn’t about to take the train a second time. His flight from L.A. to Chicago arrives Sunday night.

At the same time, I was preparing my own travel plans to the show. After years of flying somewhere on what seemed like a weekly basis at time, the last year and a half has been a pleasure. I’ve managed to avoiding flying except twice in 2008 as most of my travel has been to Red 7 Media’s offices in Norwalk, Connecticut via Amtrak. That three hour trip from BWI to Stamford is a relaxed ride, internet the entire way … uber productive. I’m earning some serious rail miles and hearing some funny things along the way.

So I figured, what the heck. I’ll take the train to Chicago. That’s right. The train.

Washington, D.C. to Chicago on Amtrak’s Capitol Limited. A journey through the scenery of Pennsylvania, Ohio and on into Illinois. Granted, most of that travel will be in utter darkness since departure is at 4 p.m. Sunday and arrival sometime around 8 a.m Monday.

Why would I do such a thing you may ask?

Well, first off is I’m expecting a torrid pace for the rest of the year. There’s going to be more travel. There’s going to be a crazy amount of work. It’s quite possible it might be just about as busy as I’ve ever been. So … what better time than to give myself a forced timeout. As far as mobile internet has come, I’m guessing that through those Pennsylvania mountains and parts of Ohio, there are not exactly going to be a ton of high powered cell sites driving my desire for high speed. For once, I’ll have no excuse not to sit back, let the ITunes crank on the laptop in my little rail car, relax and read.

And by little, I mean literally its like 3′ 6″ by 6′6″.

My home away from home for the 16 hour journey from D.C. to Chicago. It looks big here, but alas in reality it is 4x7 basically, and that is stretching it.

My home away from home for the 16 hour journey from D.C. to Chicago. It looks big here, but alas in reality it is 4x7 basically, and that is stretching it.

The second reason is, one of my best memories with my mother is a train trip we took across the country when I was 14 years old. Following the death of my grandmother — who my mother helped take care of until she passed away from cancer — she (more than me) needed a getaway. Growing up as a single mother trying to raise me (which was quite a chore), my mother really never had the chance to take a vacation beyond something local.

She became a nursing assistant after some Reagan economics caused her to lose her college funding at Towson (which she attempted to do as I got into grade school). I can’t even imagine what she was making at the time. We had a rowhouse in Baltimore, friends in the alley … I went to Catholic school and I’m not even sure how that was affordable unless my father — who divorced my mother when I was less than one (a whole other blog someday probably) — picked up part of the tab.

The point being, this wasn’t just a vacation. For my mother and I, this cross-country trip was our European vacation, our world tour. For all we knew at the time, it would be the biggest vacation we’d ever take our entire lives.

I wouldn’t say I was a train buff, but for some reason I just was enamored with trip planning. So when she asked me where I wanted to go, I just said something about the train across America. In retrospect, perhaps I just had a fear of flying even though I had before. Who knows, surely not me.

We left Baltimore, transferring in Philadelphia to our first long distance train to Chicago. During a few hours of layover in Chicago, we went up the Sears Tower. But we couldn’t see a damn thing because of all the fog. Then we kept on going, taking a cool ass double decker train all the way to Los Angeles. We stopped at the Grand Canyon for two days on the way.

In L.A. we stayed in Hollywood and did the Universal Studios and Disneyland thing. I went to see Die Hard at a movie theater in Century City — the same complex where the movie ‘happened’. Oddly, as I’m writing this I’m watching Die Hard on TV.

The thing I remember more than the movie is that somehow as a 14-year-old kid I was able to take a Rolls Royce from the Beverly Hills Hotel (for free!) to go see a movie by myself. My mother had no interest in Die Hard, imagine that, but she wanted me to go. (She would later regret giving me quite so many freedoms at a young age … lol)

We weren’t rich. The fact is the only reason we could afford such a trip (which was far from extravagant) was using part of the small inheritance my mother got.

The Orioles were on a West Coast road trip at the same time and we saw them play in Anaheim … then again in Oakland when we hit San Francisco. And lastly, our train journey ended in Seattle. That was definitely the most scenic part of the trip. We flew home from there, because that was certainly MORE than enough train for anyone by that point.

I don’t think my mother has had such a trip since, or any major vacation beyond a few hundred miles of home. She needed that trip following her mother’s death … 20 years later she needs to stay just as strong once again as her husband has such a battle of his own against cancer.

Despite the ‘why’ of how we came about to take that cross country trip together as mother and son, I’ve since loved the train … and reconnecting with the rails these last 18 months on business.

Of course the potential downside for this particular journey is how I’m going about it.

I’m driving to Union Station in D.C. from Richmond, VA where I’m at now. Then I’m taking the train to Chicago’s Union Station. A cab to the hotel for the conference. A cab to O’Hare and flying home Wednesday. Flying back to BWI sadly, where I’ll then catch yet another train back to Union Station, where I’ll then get back in my car. Hopefully I won’t lose the relaxation I gained on the trip there.

So as I journey one-third the way across the country via the rails, I wonder if I’ll encounter some wacky people in the dining car, even meet my own version of Del Griffith (John Candy’s character) from the original Planes, Trains and Automobiles.

Perhaps I’ll see some scary mountain people — or Big Foot (pictured, right) — as the double-decker train rolls through the countryside. It could be that I’ll come up with the next brilliant idea for a Web site or television show while I relax in peace. Perhaps I’ll even start the next great American novel.

Or, quite possibly (and certainly more realistically), I’ll sleep 90% of the way to Chicago, drifting asleep to the clickity-clack of the tracks.

One thing is for certain, tucked firmly away for the night in my teeny roomette, I won’t be stuck next to Miss Loretta and her horribly smelling baloney like my boy Matt.


If you’re gotten this far, take two minutes and watch Matt’s cross-country journey story now. It’s admittedly funnier than mine. And you’ll need to see it to fully appreciate my punchline at the end of my blog.

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