Pickering lies at the southern edge of the North York Moors, and it is the town where the moor begins. A castle of Norman origin stands on a mound above the market place, with a ruined keep and walls that once held kings, and in the parish church, medieval wall paintings of saints and scenes from the Bible, found again under whitewash in the nineteenth century, cover the nave. The streets are lined with warm honey-colored stone, and the market, held weekly, has been going for centuries.
The North Yorkshire Moors Railway, a heritage steam line, runs from Pickering through the moor to Whitby, via Goathland, and the station, with its old signs and gas lamps, is a favorite for photographers. The line was built by George Stephenson in the 1830s, and on summer days the whistles of steam locomotives echo along the valley. Thornton Dale, a village a few miles east, is often called the prettiest in Yorkshire, with a stream running through, thatched cottages and flower beds.
The A169 north from Pickering is the classic road onto the moors, and a good ride. It climbs steeply out of the town, past the great hollow of the Hole of Horcum, a huge natural amphitheater said in legend to have been scooped out by the giant Wade, then runs across high, open moorland with heather, sheep and views toward the golf-ball domes of Fylingdales radar station, before dropping to Whitby on the coast. Bends are open and moderate, and the surface is generally good, but the moor is exposed, with strong winds and sudden fog. In August the heather blooms purple.
Pickering has fuel, supermarkets, pubs, cafes and hotels, and it is the best base for the southern moors. Kirkbymoorside, to the west, has a market too. The best months are May to September, with August for heather, though the moor weather can turn cold and wet at any time. Winter snow can close the high road. Sheep wander across the road, so keep your speed in check, and give walkers and cyclists room on the lanes.