He is said to be tears and sad – and he is believed to be hidden in the windows of one of the many popular shops in town.
If you find him there's even a £50 reward for the glove.
But don't worry. Jack is not a real person. He is actually made of plastic and is the modest star of a summer fundraiser hosted by the town's enterprising bowling club.
13 beautifully hand-painted forests are hidden in the windows of 13 shops.
By solving simple, inexplicable clues on trail seats, residents and visitors can find the forest, and if they look very careful, they may find Jack unningly located in one of the 13 windows.
Preparing the trail was a winter-long love labour to a few volunteer artists who were able to hide the forest in a variety of bright colour forms. From Edham cheese to giant sorbet lemons. From the clockwork orange hero to the giant scar-colored ladybug.
“Helmsley's Bowling Green is an epic community resource,” said Jack's organizer Bill Jones. “This is to raise awareness of assets that more people should enjoy.”
“The reception from the town store was fantastic,” he added. “Some people say they've already said they want to keep the painted forest when it's finished.”
The search is scheduled to run until early September, with a cue sheet available for 2 pounds in Peter Silk. Helmsley Bookshop; Browns; Elijah Todd; Court Framers; Saltbox; Cafes in the Square. Spear travel; viva hair, etc.
“We've already seen people peering into the madness in every corner of the window,” adds Bill. “And if any of them find a little jack, they'll be tied for a £50 reward. It's a very happy hunt.”