Pickering, known as the "Gateway to the Moors", is reputed to be the oldest town in the area, dating back to 270 BC when founded by Peredurus, King of the Brigantes. Mentioned in the Domesday Book, Pickering was an important outpost to William the Conqueror; thus he built a stone motte and bailey castle whose remains you can visit today.

The town is packed with things to do. At the top of the sloping market place, where a busy street market takes place on Mondays, is the parish church of St. Peter and St. Paul, where 15th century murals decorate the walls, and whose magnificent spire dominates the skyline. At the bottom of the market place is the North Yorkshire Moors Railway station where you can board the 18-mile steam railway running through the spectacular scenery of the North York Moors. Next to the station is Beck Isle Museum, home to a large collection of Victorian artefacts and fascinating local photographs.