Reverse Jail Break: How I Used A Cell As a Hotel Room

Doug Harris
5 min readOct 4, 2019

Countless people have stories, or stories told about them, about how they broke out of jail. Few report ‘breaking’ into jail. I have such a story.

In the early 1960s, I was a young writer in New York City — enjoying my first job where I could call myself a writer. My job was anything but exciting, but it was an excellent training ground, thanks to a boss with a great knowledge of and love for good writing. He helped me learn how to take the most mundane topic — episodes of such ‘classic’ TV series as The Patty Duke Show and My Mother The Car — and in 50 or so words, say just enough (but not too much!) about them that newspapers would be willing to print the synopses.

Though it had existed for a couple of decades, television only then was reaching a significant number of Americans, and papers commonly printed TV Guide-like blurbs about upcoming episodes of most series, even ones in syndication — like the ones I wrote about.

In the course of my job, I from time to time had occasion to call newspapers or television stations. Being me, I took every opportunity to ‘chat up’ every interesting- (and young-) sounding woman. On more than a couple of occasions, only one of them with a legitimate business basis, I spoke to a woman with a nice Maine accent at a TV station in Portland, that state’s largest city.

Portland’s population currently is around 66,000. Then, it was around 72,000. It is, in other words, a small city. Then, like most American cities of its size, it was relatively unsophisticated. Life moved at a comfortable pace, crime wasn’t a big issue. And the local jail sat empty a good deal of the time.

Without bothering to tell her, I decided to go visit that young lady — I’d established she was close to my age plus a few other details in our phone conversations — and I took a couple of days off from my job to do so.

As a kid in Kentucky, I used to hitch-hike everywhere — to my job as a caddie at a golf club some miles from my home; to farm jobs picking potatoes and strawberries, to the store on chores. Hitch-hiking was a bit of a concern even of parents then, but it was widely accepted as a way for the less-advantaged (and people off bus lines) to get from place to place. I saw no reason why I shouldn’t…

Doug Harris

50+ years a writer, 80+ unique bylines. Two blogs have reached 60+ countries.