Distance: 17km (10.5 miles)
Height Gained: 640m
Public Transport: Bus X43 runs from Weymouth to Lulworth Cove four times a day during the summer holiday. Otherwise…
Parking: Pay car parks at Lulworth Cove and along the front in Weymouth (though the latter is considerably cheaper for day parking).
A strongly front-loaded day whose dramatic chalk undulations around Durdle Door and White Nothe gradually give way to the gentle sands of Weymouth Bay.
Cross the massive car park behind Lulworth Cove and follow the obvious pitched path up the side of Hambury Tout, the first climb of a serious morning. As a section of the path has collapsed into St Oswald’s Bay, follow the new fence to a gate below the Newlands Farm campsite and then turn left down the main path towards the chalk cirque of Man O’ War Cove, an idyllic spot for an early dip. The headland and line of rocks offshore are outcrops of hard Portland limestone, through which the impressive arch of Durdle Door is carved. Its name comes from an Old English word for a hole.
The coast path follows the line of precipitous chalk cliffs over to Scratchy Bottom, the first of a series of dry valleys dropping down to the shore. In between you climb over Swyre Head and Bat’s Head as the path rolls exhaustingly but to dramatic effect – the latter is thought to resemble a bat’s head with the tiny arch of Bat’s Hole its eye and said to glow red with the setting sun twice a year. From the headland there are stunning views along the inaccessible Lone Beach, dominated by the vertical chalk column of Fountain Rock. The ground finally flattens out after passing the navigational obelisk that helps guide ships into Portland Harbour, and stays along the edge of the fields to reach the Victorian coastguard cottages at White Nothe (meaning ‘white nose’).
Turn right then left onto a tarmac track, before branching off through the vegetation behind the shattered cliff. Stay along another track into Ringstead village, turning left at the road end by the shop as a track continues along the shore. A number of paths lead down to the shingle of Ringstead Bay, but the route weaves through the dense scrub and eventually climbs up past the observation posts on Bran Point. They are part of the World War II radar defences along this stretch of coast, whereas the now-converted Upton Fort just inland was a Victorian battery. On the rocks below is the wreck of The Minx, a coal barge that was washed across the bay from its moorings in Portland Harbour one night in 1927.
Descend steadily to Osmington Mills, where you emerge by the Smugglers Inn, originally the innocent Crown Inn but renamed in honour of the nefarious activities of its former landlords. Follow the road right for 300m and turn left up a narrow pathway; keep left where the Dorset Ridgeway branches off, an alternative inland path to West Bexington. At the top of the hill, the prominent mound of Goggins Barrow, a possible ancient burial chamber, is partially devoured by the cliff ahead. The route stays inland beneath the willows, then bears left through the campsite to cross the grassy slopes of Black Head. A rather unnecessary alternative route follows the fenced path alongside, rejoining to skirt around the activity centre above Osmington Bay. Follow the edge of the broad fields beyond, tiptoeing around the collapsed edges of Redcliff Point before descending towards Bowleaze Cove. On the downs inland you should see Osmington White Horse, a representation of King George III on horseback to commemorate a royal visit in 1808 – it is said the designer commit suicide after the King took offence that it portrayed him leaving the town.