At the time of King Richard III, Middleham was an important market town and political centre.
Middleham Castle is now hidden from immediate view from the roadside, but you'll soon find it behind the houses in the market place. It was Richard III's childhood home and extensive remains of the fortified palace can still be seen. This is the best place to start your Middleham visit. Children love to run over the drawbridge into the castle, crossing the dry moat. On a clear day you'll enjoy fantastic views of Wensleydale from the viewing platform. A small exhibition highlights the castle's history and there's a replica of the 15th-century Middleham Jewel which was found nearby. English Heritage hold some excellent recreation events here.
Richard III came to learn the skills of knighthood, and even now there's something a little stately about Middleham. From the castle walk a little way up the hill to see the gallops, the area on the High Moor where race-horses are trained. If you come early in the morning, it's a particularly imposing sight to watch the horses galloping on the misty moor and then clip clopping down the hill to their respective stables. Middleham has around 15 racehorse trainers and stables and is home to over 500 horses. Look out for details of the Open Stables event around April each year or arrange to take a tour with Middleham Racing Tours. There are about 15 racecourses within a reasonable distance of Middleham so it's no surprise that it's become such an important training ground for horses and jockeys.
As you wander around Middleham, look for the signs detailing some of its history in the market place and note the finer details of the buildings. It pays to peek through alleyways and courtyards: you'll either spot a fine view of the surrounding Wensleydale hills, horses looking over their stables or some stunning architectural features. In 1607 it is documented that Middleham was important enough to have a Royal Court. At that time all residents of the forest of Wensleydale fell under its jurisdiction.
You'll notice that many of the houses around the market place were built around 200 years ago, which is also when many stables were established. When you've enjoyed browsing around the market place and discovered the antique shops, there's an excellent choice of pubs for a meal or drink. The White Swan is the most upmarket, while across the road you'll find the Richard III where jockeys, stable hands and locals meet to exchange gossip and racing tips over home-cooked food.