A Turning Point

Since I’ve been sick and have had no adventures lately, let’s take a blast to the past, before Smokey Da Van (either of them), and look at a turning point in my life — one that sent me down the path of full-time life on the road.

After getting out from under my money pit of a house, I could finally afford to pick up a cheap well-used conversion van to dip my toes into van life. I called it the Black Pearl. I did a simple no-build build in it, with a basic bed, a free table I picked up at an office clean-up, my trusty Jackery 240, and an old cooler. This picture is from my very first camping trip around Memorial Day, 2020. It was an odd time, with people still hiding inside at the beginning of the pandemic, but before realizing that camping was one of the only activities we were still allowed to do, so we had the place practically to ourselves. I was still hobbling around with a broken foot at the time, but with a handicap-accessible campsite and Trisha’s help to do what I couldn’t, we made it work.

Once I was back on my feet again at the end of summer, Trisha strongly encouraged me to take a longer trip by myself. This would give me a good taste of what life on the road was like, beyond the quick weekend getaways we’d been doing so far. She and I didn’t work out in the end, but on this point, she was absolutely right.

I took a week-long trip from my home in New Hampshire to Maine. I stayed off the highway, which led me to roadside attractions like this random steam engine and caboose next to an old railroad bridge. Classic New England, right here.

I spent an overnight at the oddly named Height of Land in Maine. When I lived in Maine I visited from time to time on motorcycle rides, but back then there was just a tiny dirt pull-off. Now there’s a large paved parking lot with a distinct lack of “no overnight parking” signs. I spent a night with no hassles at all. I had this amazing sunset over Mooselookmeguntic Lake (don’t ask me to pronounce that), and a spectacular night sky that my phone couldn’t get pictures of.

The next morning I opened my side doors to this view of fog hanging low over the lake. I’m running out of adjectives to describe what a great experience this overnight stay was for me. What’s another word for “thesaurus?”

Today, Facebook showed me “memories” from my stay here, three years ago today. That’s what got me thinking about this trip and how it influenced where I am today, and made me decide to write this post about it.

I proceeded east across the state to Fort Knox. No, not the one where they keep the gold, but the one along the Penobscot River in the middle of Maine. Why was there a fort in the middle of Maine? Both in the Revolutionary War and the War of 1812, the British invaded from Canada all the way to the Penobscot River. They also sent warships up the river to attack Bangor and Hampden. Soon after the War of 1812, Fort Knox was built at a pinch point in the river to prevent this from ever happening again. Now the public can go explore it, check out the old cannons, and all that fun stuff for a history nerd like me. I also took the elevator up to the Penobscot Narrows Observatory for the first time. This, as well as the current bridge over the river, was still under construction during the first few years I lived in Maine.

My next stop was Acadia National Park, the only National Park in all of New England. I had no need for an America the Beautiful annual pass at the time because I wasn’t traveling enough to justify the cost of one. Today, it’s a no-brainer for me to have one.

I’d been to Acadia a few times before, my previous visit being a motorcycle day trip out of Augusta right before moving back to Massachusetts. I drove the auto loop and visited many of the sights, which were pleasantly uncrowded thanks to the tourist season being officially over. Cadillac Mountain is always a favorite of mine.

While in the neighborhood, I visited the Seal Cove Auto Museum, where an online friend of mine was the associate director at the time. He gave me the grand tour, and even took me behind the ropes of some exhibits, particularly the 100-year-old motorcycles on display. We discussed collaborating on researching and documenting more of their history together, but that never came to be.

Although I’d taken the week off from my full-time job for this trip, I made it a point to not take time off from my side gig at RideApart. I wanted to try working from the van to see what it was like. I only had my phone’s built-in hotspot, and at times I struggled to find service. I remember spending a couple of hours in a gas station parking lot after coming out of an overnight campsite in the woods with no service to get a bit of writing and editing done for the weekend’s stories.


If you’ve been following my adventures here, you’re probably seeing a lot of common themes between this trip and what are now my normal travels.

  • Random roadside stops
  • Scenic places
  • Amazing overnight stops
  • Historic sites
  • National parks
  • Museums
  • Visiting online friends in real life
  • Working on the road

This week-long trip turned out to be the perfect preview of what my life would become. It also taught me that I could be happy living on the road full-time, and capable of doing it, work and all. This was my first taste of the life I have today.

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