From the Smugglers Inn in Osmington Mills, cycle the hills and absorb the sights, to Lulworth Cove. Pass through the village of Osmington to admire the White Horse from the high ridge of Coombe Bottom to then descend and rise again at Ringstead. Enjoy the wide views from St Aldhem’s Head in the East to the Isle of Portland in the West. Follow the paths of the original Customs Officials while they patrolled the cliff tops for smugglers, passing White Nothe, Scratchy Bottom and Durdle Door. Meet the road at Daggers Gate, with its own little legend, to then cycle down to Lulworth Cove.
Distance: 9.5 miles/15km
Time: 3 hours
Total climb: 950ft
Max height: 540 ft.
Min height: 0 ft.
Terrain: Track, path, road and field.
Exertion: Medium. Some steep but short climbs.
Start: The Smugglers Inn (Postcode: DT3 6HA, Grid Ref: SY735817, What Three Words: hedgehog.feast.fleet).
Map: OL15 Purbeck and South Dorset
How to get there: From Weymouth travel east on the A353. On entering Osmington village, take the second right following a narrow road to the sea. The Smugglers Inn is in the valley at the end, the car park to the right.
Hidden down the winding road and nestled in the narrow valley of a little stream, this idyllic spot, with origins dating from the 13th century, was understandably a haven for smugglers. The most notorious of these was Emmanuel Charles who had complete control over the coastline from The Isle of Portland to Swanage during the 18th to 19th centuries. Landlord of The Crown (now known as The Smugglers), he was often helped in his exploits by gentry, vicars, commoners and even customs officials, his work proved to be profitable. However, one day he was tracked down to the Smugglers Inn by the more determined officers, but escaped capture by hiding in the chimney!
From the pub, cycle up the village road to a T-junction with the A353. Turn left and take the next right when you enter into the village of Osmington.
Often forgotten in favour of Osmington Mills, Osmington is famed for its White Horse, carved into the chalk hillside to honour King George III in 1808. This was due to his visits to Weymouth and the subsequent positive development it had on the town. However, he took offence to the horse, interpreting its direction of travel as a hint from the locals to leave and he never returned again.
When the road curves around to the left, take the track leading you up the hill on the right. Head straight through the gate and continue up Coombe Bottom to Pixon Barn while the views open up all around you. Ahead the coastline disappears to the east. Behind is the Isle of Portland and beyond, Chesil Beach disappearing to the West. Inland you can make out the White Horse, looking down upon the village of Osmington. When you reach the barn, there is a cross roads of tracks. Take the right hand option, downhill, gradually getting steeper towards the end.
At the bottom, where you meet the main road for the second time, turn right and then left onto a smaller road, climbing up the hill towards Ringstead. Ignore the sign directing you down to the village and continue to cut straight through the National Trust car park. The village of Ringstead used to be much bigger, but now it is mostly earthworks. Its downfall suggested as being due to the arrival of the plague in the 14th century from nearby Weymouth.
The theme of smuggling continues in the bay below with Ringstead proving to be an ideal landing spot and the village being a home to many involved. While the smugglers would have kept in the shadows of the valleys, this ridge would have been patrolled by the many officers trying to stop them.
Follow the track down to Sea Barn Farm and back up the other side, skimming it on your right hand side. Pass through another gate and at the top you glide past White Nothe, a chalk headland pointing out to sea. While on your left, the valley dips at Chaldon Down, the old Down Barn being the only building clear in the landscape.
Head through the next gate and cut straight across the field, passing between two large pyramidal shipping beacons, the tip of one only visible as the cliff drops to the sea. The views stretch out toward the east and the high cliffs of the cove become more recognisable. Make your way through another gate in the dip and then rise again, the peak marked with a telegraph pole.
The views capture a huge expanse of the coastline. The peninsula of St Aldhelm’s Head is as far as you can see to the east, Portland still dominating the west.
Once through the next gate, you enter into your first deep clifftop valley leading down to Bats Head. After the following gate you enter into the second deeper dip of Scratchy Bottom that leads to Durdle Door. It was used as a location on the 1967 Thomas Hardy film ‘Far From The Madding Crowd’, where, in the opening scene, Gabriel Oak’s sheep are driven off the cliff to their death by his own sheep dog, which he then shot.
On entering Scratchy Bottom, keep left, climbing up another hill to the top but then providing you with a quick run to meet the road at Daggers Gate. This ancient crossroads is believed to mark a witch’s grave. Her ghost is said to haunt the area and appear in the form of a hare. After her death her own daughter, back in 1789, returned to this exact spot, but not to wish her mother well, instead to brutally murder Sam Varnell, a local farmer, stabbing him to death. It was this tragedy that gave the crossroads its name.
At the junction you have a choice:
You can either continue straight over, following the track up the hill, the views opening up further to the east. The large Hillfort of Bindon Hill blocks the coastline, but beyond, the glimmer of Worbarrow Bay and the peak of the Worbarrow Tout can both be seen. At the end of the track, meeting another road, turn right to ride down into Lulworth.
Alternatively you can turn right at Daggers Gate and follow the road straight down into the village.
Once at the bottom, for both routes, follow the road to the sea. Passing the Lulworth Cove Inn on your left, heading straight to the Cove is a must do. Its unique geology creates breath-taking scenery that, along with the entire route, is all part of the world famous Jurassic Coast – a UNESCO World Heritage Site.