RUTLAND — Just in time for Halloween, the Mystery Jack O’ Lantern contest is back for another year of fun! A tradition of the Rutland Halloween Parade, this contest keeps participants guessing until the big reveal at the parade’s finale. Rutland residents of all ages are invited to solve the riddle and submit their guesses for a chance to win frightful prizes.
This year’s contest introduces a brand-new pumpkin head for the Mystery Jack O’ Lantern, as the previous one retires after years of service. The Mystery Jack O’ Lantern will ride on a Haunted Island-themed float designed by Miss Lorraine’s School of Dance.
The following riddle offers plenty of clues for Rutland residents to uncover the identity of the Mystery Jack:
“Gather round, Rut-riddlers, it’s that spine-chilling time,
When pumpkins grin, and curses bind.
Darkness creeps as shadows grow,
With mysteries only the strange can know.
The 64th Halloween Parade is nearly here,
And the Mystery Jack O’ Lantern draws near!
Guess who’s lurking behind the mask,
Solve the riddle—it’s no easy task.
This Jack is tall, with a Bostonian start,
Yet Rutland holds a place deep in their heart.
From teaching teens to a leader’s post,
They’ve haunted the schools, like a friendly ghost.
A quiet soul, but don’t be fooled,
They’re the reason learning is cool.
They recently traveled to Japan,
And taught and lived in far-off lands.
They savor lobster, pizza, and lasagna too,
But if you need more clues, here’s a few:
They’ve crossed paths with three popes and a president,
Glimpses of history, rare and eminent.
So who’s the figure behind the Jack?
A sage in learning, now stepping back,
A community legend with a heart true,
The answer to this riddle rests with you!”
Residents can submit their guesses online at comealiveoutside.com by Friday, Oct.25, at midnight. Winners will be drawn from correct guesses and awarded special prizes on Oct. 29.
For more information, visit comealiveoutside.com.
