He’s described as tearful and sad – and he’s believed to be hiding in the window of one of the town’s many popular shops.
There’s even a £50 reward up for grabs if you find him.
But don’t worry. Jack isn’t a real person. He’s actually made of plastic and he’s the unassuming star of a summer-long fundraiser organised by the town’s enterprising bowling club.
Thirteen beautifully hand-painted woods have been hidden in 13 shop windows.
By solving simple cryptic clues in a trailsheet, residents and visitors can locate the woods, and if they look very carefully, they might find Jack – cunningly positioned in one of the thirteen windows.
Preparing the trail has been a winter-long labour of love for a handful of volunteer artists who’ve managed to disguise the woods in various brightly-coloured forms. From an Edam cheese to a giant sherbet lemon. From the lead character in Clockwork Orange to a giant scarlet ladybird.
“The bowling green in Helmsley is a magnificent community resource,” said Where’s Jack organiser Bill Jones. “This is about raising awareness of an asset that should be enjoyed by many, many more people.”
“The reception from the town’s shops has been brilliant,” he added. “Some have already said they’d like to keep their painted woods when it’s all over.”
The search is scheduled to run until early September with clue sheets available for £2 at Peter Silk; Helmsley Bookshop; Browns; Elijah Todd; Courthouse Framers; Saltbox; Café on the Square; Spear Travel; Viva Hair and others.
“We’ve already seen people peering into the nooks and crannies of every window,” adds Bill. “And if any of them locate little Jack they’ll be going into a draw for the £50 reward. So happy hunting.”






































