Win Green

Win Green is a proper walk, full stop. This chalky peak rises to 910 metres near Shaftesbury and commands views across Dorset that'll make you understand why people settled here thousands of years ago. There's an Iron Age hill fort at the summit - you can still pick out the defensive banks if you know what you're looking for, though the earthworks aren't exactly dramatic by some standards.

The climb itself takes around forty minutes from the nearest car park, depending on fitness. It's steep enough to warrant proper shoes but not technically difficult. On a clear day you're looking at views that stretch to Oxfordshire on the north side and down towards the coast on the south. The wind up there is relentless, so come prepared.

History buffs will appreciate the Iron Age significance, but I won't pretend this is a rampart-heavy experience like some forts further south. What you're really paying for is the walk and the panorama. Families with younger kids might struggle with the gradient, though teenagers keen on a bit of exertion would find it satisfying. Allow three hours round trip if you're not hurrying.

Both Gold Hill Glamping and Chalke Valley Camping sit within easy striking distance - your glamping spot is basically four miles away. Pair this with a visit to nearby Shaftesbury's high street and you've got a proper half-day sorted. Worth doing? Absolutely, if you like elevated walks with genuine views rather than just the ascent for its own sake.