The small sculpture of The Boy with the Leaking Boot has been a fixture of Cleethorpes since 1918. Donated to the town by shipping magnate, John Carlbom. A Swedish immigrant to Cleethorpes who had built a successful shipping business, the statue is a copy of one in Stockholm, Sweden. It is unclear as to the exact story of the boy with the boot. Several statues appeared in the US in the late 1800s and were thought to have been purchased in Europe by wealthy travellers.

Despite the unknown origins, the sculpture remains a firm favourite of visitors who can find him in the Kingsway Gardens along the promenade.