Chesterfield

That twisted spire poking through the skyline isn't a medieval architectural accident - it's Chesterfield's calling card, a 14th-century church tower that warped as its timbers aged. The market town sprawls beneath it with a no-nonsense Derbyshire character that's refreshingly unpretentious.

Chesterfield proper feels like a working town that happens to have tourists rather than the other way round. The market square buzzes on Saturdays, while midweek sees a quieter pace that suits the locals just fine. It's not trying to be the Cotswolds, and that's precisely its appeal.

Just west of town, the Linacre Reservoirs offer proper walking territory. The three reservoirs - Upper, Middle and Lower - thread through wooded valleys that feel surprisingly wild for somewhere so close to Sheffield. Linacre Lower Reservoir gets busy with dog walkers, but push on to the upper reaches and you'll find space to breathe. The Lower Car Park makes a decent starting point for circular walks that'll work up an appetite.

Old Brampton, a few miles southwest, rewards the short drive with St Peter & St Paul Church and views across the Derbyshire countryside. The area around Holymoorside reveals centuries-old boundary stones that mark ancient parish limits - not spectacular, but the kind of detail that makes wandering these hills more interesting.

From the various glamping spots and caravan sites scattered around Chesterfield's edges, you're well placed for day trips into the Peak District proper. Chatsworth lies 20 minutes south, while the Pennine trails beckon from the west. Chesterfield train station connects directly to Sheffield and Manchester, making it surprisingly handy for exploring both industrial heritage and proper countryside within the same fortnight.