The High Weald of Kent is a landscape of small fields, sunken lanes, oak woods and oast houses with their white cowls turning in the wind, and Cranbrook sits right in the middle of it. The town is small, about four and a half thousand people, with white weatherboarded houses and the tall Union Windmill rising over the rooftops, one of the finest working smock mills in England.
Cranbrook grew rich on cloth. In the late Middle Ages Flemish weavers settled in the Weald, and the broadcloth made here was sold across Europe; the big church, sometimes called the Cathedral of the Weald, was paid for by that wealth. In the eighteenth century the area had a darker reputation, as the Hawkhurst Gang, a notorious band of smugglers, ran contraband through these lanes from the coast and terrorised anyone who stood in their way. A few kilometres north, Sissinghurst Castle is home to the famous garden made by Vita Sackville-West and Harold Nicolson in the 1930s, with its White Garden and its brick tower, and it draws visitors from all over the world.
On swimming, be realistic. There are no natural lakes here, and the rivers are small. Bewl Water, the big reservoir a few kilometres west, is the nearest large body of water, and while it has hosted organised open-water swimming at times, free swimming is not allowed. If you want to cool off, a shaded pub garden or the woodland at Bedgebury, the national pinetum near Goudhurst, may be the better plan.
The riding is the real pleasure of the Weald. The roads twist and dip constantly, with short steep climbs, blind crests and tight bends between hedges, and the surface can be patchy, with gravel at junctions and mud from farm gateways. In spring, the woods fill with bluebells, and in autumn the colours are rich. Traffic is light on the lanes, but be ready for horse riders, cyclists and wide farm machinery around every corner.
Cranbrook has cafés, pubs and shops, and fuel can be found nearby. Tenterden, about eight kilometres east, is the nearest larger town, with a broad tree-lined high street, its own steam railway and good services. Hawkhurst and Sissinghurst are close too, and the ride home towards London can be as fast or as slow as you like.