Gold Hill is one of the most famous streets in England, and you have probably seen it without knowing its name: a steep, cobbled lane lined with old cottages, curving down from the top of the town, with the green fields of the Blackmore Vale spread out below. In 1973 it featured in a television advertisement for Hovis bread, directed by a young Ridley Scott, which became one of the best-loved adverts in British history. It is too steep and cobbled for bikes, so park in the town and walk down.
Shaftesbury sits on top of a greensand ridge, high above the surrounding countryside, and it is one of the oldest towns in Dorset. King Alfred the Great founded an abbey here in the late ninth century, with his daughter as its first abbess, and it became one of the richest nunneries in England, especially after the relics of the murdered King Edward the Martyr were brought here. Only the foundations survive, in a peaceful garden next to Gold Hill. Thomas Hardy called the town Shaston in his novels.
The views from Shaftesbury are wonderful, stretching over the Blackmore Vale to the west and Cranborne Chase to the east. Cranborne Chase is an area of rolling chalk downland, woods and valleys, once a royal hunting ground, and it has some of the best riding in southern England. The B3081 east of Shaftesbury climbs Zig Zag Hill, a short series of tight hairpin bends up the scarp of the downs, before continuing over the Chase through beautiful, quiet countryside.
The town has a good selection of cafés, pubs and restaurants, and the high street is lively, with independent shops. Fuel and other services are available. The lanes around Shaftesbury are narrow, often sunken between high hedges, with blind bends and steep gradients, and they can be muddy and slippery after rain. The weather can be changeable, and on top of the ridge the wind can be strong, but on a clear day the views make it all worthwhile.