This post was inspired by a New Yorker piece by Colin Jost.
As a teenager, I lived on the east side of the Humber River, but attended high school west of the Humber. If we're talking boroughs, I lived in York and went to high school in Etobicoke. There were precisely three ways I'd get to high school.
The Red Rocket
The Red Rocket is a bit of a misnomer here, because on the Bloor line we no longer saw red subways when I was in high school. It was all grey by '89... rosy and grey. There was a Jane 35 bus that I'd hop on (luckily it came every two minutes) and then take the subway from Jane to Islington station. Then, it was a good ol' fashioned walk.
The Lambton 40
Sometimes, if the timing was right, I'd hop on the Lambton 40, a bus that took you from Jane and Dundas to a stop right across the street from my high school. With the Jane bus / subway combo, timing didn't matter because the bus and subway came all the time, but with the Lambton 40 route you definitely had to know the schedule because it was a far less frequent bus. The advantage to this route was that you could listen to the radio!
At some point in grade ten I realized it was a pretty easy bike ride to high school, and on your bike you could listen to the radio on your Sony Walkman. During the warmer months, I would bike Dundas to Power and the bike I'd ride is currently rusting in my backyard as a monument of sorts.
Those were the three ways I'd commute to high school, and although sometimes I'd see a friend on the bus or subway and chat them up, it was typically just me and my Walkman. Often I was listening to the radio, but for the subway ride I'd always have a favourite cassette or two. Sometimes it was an album (I think Public Enemy and The Clash were in there for months at a time) but often it was a mix tape I curated with great love and care for the purposes of commuing to high school.
And although my Edmonton-raised wife makes fun of this fact, I attended high school for five years. My oldest two kids have finished high school and have gone on to university, and somehow they managed to do it in four years. But we had five. (Shout out to FOTM Colin James.)