Thomas Skelton was a trusted servant and steward at Muncaster in the 16th century. His master was Sir William Pennington. Known for sitting beneath an old chestnut tree outside the front entrance of the castle, Tom Skelton was often asked for directions. This position also gave him opportunity to witness the comings and goings of people to and from the castle. When a traveler asked for directions he looked them up and down and if a traveler he liked he given the correct directions. If he didn’t his directions would lead to certain death - bogs, swamps or bandits. So comes from this time the old saying - Tom foolery.

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