The best-ever Aspen Halloween prank |

The best-ever Aspen Halloween prank

Tim Willoughby
Aspen Times Weekly
Aspen, CO Colorado

My father’s generation of Aspen boys pushed over outhouses on Halloween – or so he told me – but it sounded more like he had heard that other boys had done that. These days, Halloween pranks are considered criminal.

When I was in high school, kids took a certain amount of pride in the pranks they pulled. Creativity was admired; traditional mischievous behavior like toilet-papering a tree, or soaping a window neither raised an adult eyebrow nor earned points with peers.

Unfortunately, when I was a freshman the ultimate prank was perpetrated – one that no other class of boys could top – so the prank-tradition faded. Who could top putting heavy wagons on a rooftop, especially on the top of the school gym (one of the higher buildings in town), unless you put the horses up there too?

That ultimate prank occurred during the days when the Aspen police department did not have radio dispatch. If there was an emergency, citizens phoned the Hotel Jerome. The night clerk who took the call would run to the rooftop where he would turn on a spotlight that shone on the mountain. The patrolling officer, seeing the light, would drive to the Hotel to get the message.

Halloween always challenged Aspen’s police. With only one car and officer, youth were free to perform their pranks at one end of town when they observed that the patrol car was at the opposite end. You would think that police would figure that the high school was a logical place to patrol on Halloween, but no one did so apparently on that October night of 1963.

There was great excitement when students arrived at Aspen High the next day. Everyone wondered how anyone could have placed wagons that weighed tons atop the gym. Students speculated on who could have pulled if off. Seniors were the obvious suspects, and all during the day members of that class were seen entering and exiting the principal’s office. No one was publicly incriminated, except through unsubstantiated gossip, but some senior boys were seen to be helping when the wagons were removed. Getting them down required more than muscle, as a wagon could easily weigh as much as a car; as I remember, it took several days before they figured a safe way to get the wagons down.

Trying to trace down the story of that Halloween is as interesting as the actual episode. After nearly 50 years, who did it remains a mystery. When I asked acquaintances about the event, each responded with a different version of the story. Although we are all aging baby-boomers, none of us is experiencing Alzheimer’s!

Some had no memory of the incident. Some remember it, but were sure that it had taken place when we were in junior high. Some remembered it taking place during high school, and then went on to try to remember who the principal was at the time. Those acquaintances immediately tried to figure out who might have put those wagons up there.

Several of us remember that a photograph of the prank was published in the school year book, but the Aspen Historical Society’s yearbook collection is incomplete by only one year, 1963.

So, dear readers, I challenge you. Someone knows the real story. The statute of limitations has long since passed. ‘Fess up. If you e-mail me the details, I will publish them. Somewhere, someone has a 1963 yearbook; scan it and pass it along. Send me remembrances of that Halloween and other similar pranks. I’ll put it all together for next Halloween. Sharing the stories of Halloweens Past could be as fun as perpetrating the pranks themselves.

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