The Amateur American Hobo: Winnipeg to Toronto (Part IV)

by macksemil

Winnipeg was a sprawling, unfamiliar city. We wandered around the streets, read by the river, had coffee and traded some books in. I had a contact that could offer us a place to stay by the University named Quincy, so we made our way to his part of town. He lived in a one-room apartment with just enough floor space for Bob and I to roll out our sleeping gear. I took a nice shower, the first in a number of days. Quincy fed us some great curry with rice and we all stitched our torn clothing up and visited until it was time to sleep. Early in the morning we woke up and headed out, killing time in Winnipeg before heading to CN’s Transcona yard at dusk.

It wasn’t quite dusk when we arrived so Bob and I ate some pizza in a nearby park before walking over to the tracks once the sun went down. We found the mainlines and decided to wait west of the yard hoping to find the back end of the next eastbound train. There was a thicket of small trees and bushes not far away, so we found a trail leading inside and waited.  Once the sun had completely set the air grew cold. Bob and I pulled layer after layer of clothing out of our bags until none were left. We decided to build a small fire to warm up with. After the necessary sticks were gathered Bob got the fire going. We fetched a couple of ballast rocks and warmed them by the fire. Once they were heated, we wrapped our bandannas around a few of them and put them in the bottom of our sleeping bags. Warmed by the ballast rocks, we drifted off to sleep.


The whistle of our train woke us up as we scrambled to get our sleeping bags put away. The train rolled past us but we could see the flashing red light at the rear of the train up ahead in the distance. We shouldered our packs and started off on a quarter mile run to the end of the train. Winded from the run, Bob and I climbed up the ladder and into the well of a 53 foot container car close to the rear of the train. We immediately rolled out our sleeping bags again and fell asleep.

Shortly we heard the crunching footsteps of another person walking on the ballast rocks by the train. Then the clunk clunk clunk of feet coming up the ladder on our car. I roused from my sleep and looked up to see a figure silhouetted by the deep blue sky standing above the well about to jump in. The figure threw a few containers of food into the well. “Hey hey hey! Someone’s in here!” I called out to him. “Shit!” he replied, climbed back down, and continued up the train.  We could tell from the sounds of footsteps that he wasn’t alone. Soon the train filled the air brakes and started rolling. The wind from the movement of the train added to the chill of the air, so I tightened the drawstrings on the opening of my sleeping bag.  I drifted off to sleep, rocking slightly back and forth.

I awoke to an unfamiliar voice. “HEY BOYS!” Straining to yell over the train noises and wind, a figure was standing on the edge of the well car. “CAN I COME IN?” I struggled to free myself from the tightened drawstring trap and realized that the train was still traveling full speed. Whoever this was had just walked down the side of a container car on a six inch metal beam. On one side of the beam was a 15 foot vertical wall of shipping container. The other side was seven feet down to the ballast rocks going by at roughly 65 miles per hour. One false step would have led to near certain death. Bob granted the stranger permission to come into our well car and he dropped down from his death-defying perch.

He produced a plastic bag and two beers from his sweatshirt pocket. Inside the plastic bag was some slices of pizza he had dumpstered on the way to the train yard. He introduced himself as Quiggly. He had been riding the rails in Canada for 6 years and explained the whole ride between Winnipeg and Toronto to us. He was riding with four friends who were in the next well up. Apparently they had been waiting in the Transcona yard in Winnipeg and had been found by the railroad bulls. The bulls kicked them out of the yard. The bulls had told Quiggly they were coming to get Bob and I too (“your friends in the bushes”) and were shining spotlights in the bushes and the rear of the train. We must have unintentionally timed the exit from the bushes and approach to the train perfectly because Bob and I had no idea. After telling him our story and finishing the beers together, he got up and balance-beamed on the wall of the shipping container back to his car, defying death again as the train screamed through the night eastward.

Bob and I woke to an overcast sky, the daylight had not added warmth to the air. We didn’t stay out of our sleeping bags for long. The fall was quickly approaching. We watched the scenery go by all afternoon. We saw hundreds of small lakes surrounded by quaint cabins. There were a few fishermen on the lakes but at most times we were looking on an uninhabited landscape. We spent the day mostly in our sleeping bags staying warm. Every now and then we would share a tin of tuna or a bag of mixed nuts or stand up to look at passing lakes. We slept heartily. In the morning, Bob and I woke up to realize that we were stopped. We looked around and realized that we were out in the west end of a train yard and that our cars had been cut out of the train. We got our things together, and woke up Quiggly and his crew in the next car up. We all walked up to where the rest of the train was still sitting and found new rides. Within a few hours we were back on our way.

The rain stated coming down a few hours later. A light, early fall rain. Bob took his large tarp out of his bag and we put both of our bags under it to keep them dry. Bob and I leaned our backs against the container, the speed of the train creating a little dry pocket that we took advantage of. The train wound through fields in flatlands by country roads through the autumn mist. Shortly after nightfall we began to see the city lights of Toronto. An hour later we were throwing our backpacks off of the train, followed by our running boots on the ballast rocks. Quiggly and his crew did the same and we parted ways without ceremony. A few fences later and we were released onto the dark and unfamiliar streets of Toronto, Ontario. We set out in search of a bus stop, a map of the city, and a dry place to sleep for the night.