Dog-friendly Portland

Eighteenth-century inn built into the sea wall at Chiswell, looking straight down the length of Chesil Beach. Dogs are permitted in the bar and on the Madeline Tristan side of the restaurant, kept on leads under the table and off the benches. Storms break over the wall in winter, which is when regulars like it best.

A 3.4-mile loop of the island’s southern tip in an hour and three quarters, out past the red and white lighthouse, up the east side above Cave Hole and Freshwater Bay, then back through Southwell on lanes and field paths. Almost flat at 60 metres of climb, but the going is bare limestone, quarry spoil and stone stiles that a big dog will need lifting over. Park at the Portland Bill pay and display beside the lighthouse, a large open area that still overflows onto the verges when the sea is up and the spray is worth watching. The clifftop has no fence and old quarry shafts and gullies open without warning right beside the path, so this is a lead walk unless recall is faultless; there is a water bowl at the Lobster Pot café.

Two and three quarter miles of wandering through two abandoned Portland stone quarries, an hour and a half, with more than seventy carvings hidden in the rock faces of Tout and a level tramway track running north through King Barrow to a grandstand view over Chesil and the Fleet. Underfoot is stone chippings, bare rock and short turf, with plenty of scrambling if you want it. Start at the free Tout Quarry car park on the hairpin above Chiswell, which takes about twenty cars and has no overflow, so a Sunday afternoon may mean parking in Portland Heights instead. Sheer worked faces and unfenced drops are everywhere among the sculptures, so keep a dog on a lead in the quarry itself; the tramway section beyond the gate is safe enough for a run.