July 21–29, 2001

Michael Orr
6 min readJul 21, 2021

Freeport, Maine

Two guys in between a lifted Ford Excursion SUV and our road trip van, Modesto, California, July 3, 2001
Can’t believe I forgot to include this on our Yosemite/Modesto day! Win and Wes next to an Excursion as tall as our van. Wes could look directly into the side mirror. Modesto, California — July 3, 2001

First, a few words to wrap up our drive, which in the medium with which I’m most comfortable, really just means some stats. We drove 9047 miles over thirty-three days. We hit thirty states, eight national parks, stayed in five hotels, six Wal-Mart parking lots, and spent thirteen nights with our families, whether they were there or not. And while I don’t have the specific number, after filling the van with gas for more nearly five weeks, we still had about $200 left in our gas account!

This is also a good reminder of something I first really learned when writing my book on the Portland Timbers’ 1975 debut season ten years later: do not trust memories alone. The more time passes, the worse the accuracy of our memories are. You don’t even have to be old for this to be the case. With my book I was able to double check and cross reference anecdotes with contemporary newspaper articles to find something of a middle ground that was the likeliest thing we call truth. In this project I have my memories, Win and Wes have theirs, our parents have theirs, and then my journal gave some counter to all of those. In my mind I had a buffalo burger at Wall Drug. Well, I wrote down when I was, y’know, actually there, that I had a sloppy joe. Do these small distinctions really matter? Not especially, but given I had the journal, it was fun to rebuke those memories, but also felt good to get it right.

Why mention this? Because in my introductory post last month, I said we drove over 10,000 miles in five full weeks. Well, guess what, those are both incorrect. That’s me exaggerating over time, mostly just rounding up. No ill intention or agenda, of course, stories are just better with normal people when you say 10,000/5 weeks and not 9047/33 days. And when I started this blog, I hadn’t kept track in the tight specifics with which I eventually wrote. Anyway, it was fun to really relearn exactly what we did, after so many years. Like I mentioned many times throughout, we didn’t have internet access like we do today, so such things were just never fully dissected before, until now.

So, that’s that. Our road trip, in its entirety, and more detail than I can assure you any of us have ever thought about in the twenty years since. Or even at the time, to be honest. We had such a good time, we learned a lot about ourselves, we saw the unbelievable amount and variety of the country, and we did it before we were burdened with school, work, life. There’s much to be learned from those experiences, too, and I’m so pleased the three of us have gotten together a few times over the years and been ourselves in those specific times, but also recall the time when we were kids out there in America, finding our way, leaning on family, and making the most of the opportunity we had. We may live hundreds and thousands of miles away now, but those guys are my family, my brothers,[1] partners for life in the single most ambitious adventure we could imagine at the absolute perfect time.

Within three days of returning to Maine, we all kind of went our separate ways. Wes and Win both had stuff to do now that they were back in familiar surroundings, though my flight back to North Carolina was not until July 29, just in case it took us far longer than we expected. We all got back together on the 29th before I went back to the Portland Jetport, but most of the time in between I was on my own. Frank came down to Freeport on the 22nd (see photo with his car in the driveway on yesterday’s post) and took Win up to Wiscasset, I think. I don’t really remember. But what I absolutely do remember is that week where I was alone at Frank’s house.

Three things dominated my time: hosting or attending Freeport parties at night, hanging out with Win and Wes’ friends from high school, and reading at the house. No real reason to go into detail about the former, though I had an absolute blast and stayed in touch with those kids all through college, and with some for years afterward.

During the days I got to hang around the local spots in the area, bumming a ride any time I could, including a railroad trestle jump into a river. Those dudes made me go first, being the only one who hadn’t done it before, and I really had no idea how deep the water was or where there might be rocks. Thanks, guys! But the water was plenty deep, and the drop of twenty feet or so was an exhilarating experience I repeated over-and-over that afternoon. Those guys (Jake, Casey, and others whose names I’m sadly unable to recall) were giving me the ultimate test: trust us and you’re in. I did, and I was. I stayed with Jake for several nights on a visit the next year and was always welcomed to any gathering or party any other time I ever came through town. I’ll never forget the generosity of those folks, giving me the ultimate cool down from four plus weeks on the road.

The third thing was reading. And yeah, this is totally cliché and trite, some of the worst characteristics in the world, if you’re asking twenty-years-later me. Frank did not have a couch set up in his house at the time (not worth getting into, but it wasn’t exactly a ‘finished’ house in those days), but he did have a hammock hanging in the living room, just off the kitchen. I had plenty of time to kill, after cleaning up empties from the kitchen and back porch, so I went digging in Frank’s bookshelves. What I found was On The Road, Jack Kerouac’s famous Beat Generation fictional travel journal-ish. We weren’t listening to jazz, certainly weren’t reading poetry, and weren’t even crashing with randos across the west, outside of Yellowstone anyway, but it still landed with me at the perfect time. Before our trip the words published in 1957 wouldn’t have meant much of anything to me. But afterward, well there was a palpable link between us. It really spoke to me, man. But seriously, it really was the perfect book to read in the quiet of breezy afternoons in that hammock. Over the course of the week, or at least the days I woke up at Frank’s house, I powered through the exploits of Sal Paradise, Dean Moriarty, and Carlo Marx out there in Denver, San Francisco, and beyond.

[1] This short aside doesn’t involve Wes, but it would’ve, if he’d been in school with us in Durham. There was a fire drill at lunch when I was in twelfth grade, which was the only year my brother and sister were in high school with me at the same time. We had to go outside when the bells started ringing, and Win and I ran into my brother Brian as we exited for the back parking lots. My sister, Katey, asked by her friends who we were, responded perfectly, “my three dumb brothers.”

Seven teenagers posing for a picture in Freeport, Maine, July 29, 2001
Casey, Jake, Win, Daneel, Wes, and Zack (I think? Someone correct me if not), at the Dafni’s house, Freeport, Maine — July 29, 2001

Though the road trip proper had been done for about a week, I was still living in a bizzarro world, made even more pronounced by my lack of supervision or even uninvited company. But eventually it was time for me to go. One last get-together at Jake’s brought together my road trip partners and their Freeport friends, sending me off in fine fashion. I flew back home and spent the next six weeks or so back in North Carolina, going to the beach and kickin it with my buddies. One-by-one they went off to college, and I went with Win’s family to send him on a plane to Montreal at the end of August. Then it was my turn, I moved to Greenville, South Carolina in the first week of September, preparing for my first day of college: September 11, 2001.

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