Ludlow

The fortified walls tell the story before you even reach the castle. Ludlow commands its hilltop position with the confidence of a town that's been doing this for nearly a thousand years. Medieval streets wind down from the ruins, past Tudor timber-framed buildings that lean companionably together like old friends sharing gossip.

Ludlow Castle dominates the skyline - proper Norman fortress stuff, where the Princes in the Tower once lived before their fateful journey to London. The views from the keep stretch across the Shropshire Hills, taking in Bringewood Hill and the gentler slopes of Mary Knoll. Walking the walls gives you the full medieval lord experience.

Food matters here. Seriously. This market town punches well above its weight on the culinary front, with more decent restaurants per square mile than most cities. The weekly market still fills the square beneath St Laurence Church, where you can pick up local produce before wandering the narrow streets lined with independent shops.

Beyond town, the countryside unfolds in classic Marches fashion. Tatteridge and High Vinnalls offer proper hill walking, while the cluster of pools - Middle Pool, Lower Pool, and Burrington Pool - provide gentler waterside strolls. The Roman Camp site reminds you that people have found this spot strategic for two millennia.

Getting here means the A49 from either Shrewsbury or Hereford, though the train from Birmingham takes just over an hour. Several holiday parks dot the surrounding hills, making perfect bases for exploring both the town's medieval treasures and the wilder Shropshire Hills beyond. Ludlow repays a proper stay rather than a day trip - there's too much good eating and too many castle stories to rush.