The day started at the house of a friend and ended at the house of a stranger. As many of you know, I gave up my home last summer to become a permanent vagabond. Today I packed my two bags (one with clothes and one with food) and headed south to Oregon for a week in the town of Oregon City, the end point of the historic  Oregon Trail.

While in Seattle, I’d discovered another way to live life without paying rent: house sitting. After asking friends and visiting a few web sites, I joined a program called Trusted Housesitters. It pairs people looking for someone to watch their pets while they’re away with people who want to vacation for free. Lodging is the highest expenditure for me when traveling so if I can find a way to make it free, it extends the length of time I can travel.

I had two friends write references for me. They were in fact legitimate references because in one case I’d run an AirBnB for a friend while she was in the Peace Corps and in the other case I’d pet sat for my ex wife while she and her new husband went to visit family on the east coast. It was especially nice to enjoy my former home mortgage free.

Those references landed the current house sit along with my letter of intent expressing my familiarity with the area. I threw out the added enticement that I could meet with the owner the week prior to get to know the animals and learn their routine. I knew that gave me an advantage over other applicants as they typically only able to show up on the first day of the house sit.

I’d spent the previous week staying in Vancouver, Washington with a friend I met on a trip I hosted to Mexico last winter, and it was time for me to fly to my next nest. I put my bike on the rack at the front of the bus and carried my bags inside. Even though I crossed state lines on the bus, the adjoining transit systems allowed me to use the same pass to get all the way into Portland.

I chose to transfer to the train downtown for a couple reasons. One is that I wanted to familiarize myself with the waterfront since I had a tour planned there for the upcoming week. I wanted to do some reconnaissance to see if there were any little surprises I could educate myself on for the tour.

The second reason was so that I could pick up a gig for a friend who owns a bike tour business. She’d asked me just the night before whether I could fill in for her that day since she had other plans. Being that pickings are slim during Covid-19 summer, I jumped at the opportunity, knowing I could slip it into the middle of my journey to Oregon City. Fortunately, the bike shop has a refrigerator so I was able to store all my food in there while I was running the tour.

There were only two people on the tour, and I asked them the same question I ask everyone I meet, “where are you from?” They responded that they were from Tacoma, a town I know well, but when I asked them to be more specific, they really couldn’t tell me which part. I always find it humorous when I know people’s hometowns better than they do, but I’d never had a case where people didn’t quite know how to describe where they lived.

It was the regular tour around Portland neighborhoods and bridges. I even took them by the BLM protest site downtown as they’d heard how dangerous it was. They took pictures and videos of people lounging around in front of the federal building grilling up hot dogs and pizza. They said that would make their parents feel a lot better since, from their parents’ perspective, they’d chosen for a vacation spot a place that appeared to be a war zone on TV.

When the tour ended, I went to the refrigerator to pull out my food only to find the shelves empty. Unknown to me, the owner of the business had come by that afternoon to clean out the fridge. That included the home made chocolate bars I’d toiled over the day before. I texted her immediately, and she told me she’d indiscriminately thrown everything into a garbage bag and into the dumpster. Fortunately, she included the code to open the dumpster, and I got my first experience dumpster diving!

Chocolate recovered, I pedaled over to my favorite local burrito spot and grabbed a rolled up dinner to go. The train to Oregon City was running late so it gave me just enough time to enjoy the litre sized wrap of meat and beans while I waited for the train.

At the end of the line, I had to transfer myself and my bike to another bus, but that got me within 5 minutes of the house sit. I walked in the door and was immediately greeted by four barking dogs. Since it was past their dinner time, I went straight to their food bowls and got them fed for the evening. 

I headed out to the back porch with my glass of wine and sat under the shade trees. After a few minutes of enjoying my new temporary homeless shelter, I popped open my computer and began to work on the narrative for a tour I planned for the following evening: a walking tour of Oregon City, the end of the Oregon Trail”.