Ashbourne is a handsome market town on the southern edge of the Peak District in Derbyshire. Its long main street, Church Street and St John Street, is lined with Georgian and Tudor buildings, and the whole town has a well-preserved feel that makes it one of the most attractive small towns in the Midlands. The church of St Oswald, with its soaring 65-metre spire, is particularly fine — Dr Johnson called it "the most interesting and elegant church in all of England."
The town is best known as the starting point of the Tissington Trail, a 21-kilometre walking and cycling path that follows a disused railway line north through the White Peak limestone countryside. You can hire bikes at the old Ashbourne station. Dovedale, the famous limestone gorge with its stepping stones across the River Dove, is just a few kilometres to the north and makes for an excellent half-day walk.
Ashbourne's other claim to fame is its Royal Shrovetide Football, a wild two-day game played through the streets and fields of the town every Shrove Tuesday and Ash Wednesday. The game has been played for centuries, involves hundreds of players, and has virtually no rules. The goals are three miles apart. If you happen to be in Derbyshire in February, it is an extraordinary spectacle. The rest of the year, Ashbourne is a quieter affair, with a good Thursday market, several tea rooms, antique shops along the main street, and the Green Man & Black's Head Royal Hotel — a coaching inn spanning the centuries where Samuel Johnson once stayed.