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 infamous 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. He was the landlord of The Crown (now known as The Smugglers), later to be run by Richard Champ, another of the gang. The Customs Boards at Poole struggled to halt the illegal activity and were desperate to catch the elusive mob, but Charles was often helped in his exploits by gentry, vicars, commoners and even customs officials. One day some determined officers managed to track him down to the Smugglers Inn, armed with fresh evidence of his adventures. He managed to outsmart them by hiding in the chimney as a fight developed outside. He survived but sadly his daughter was shot on the steps.
Another notorious smuggler, who was around long before Emmanuel Charles, was Harry Payne. Harry Payne was a famous Poole pirate, born around 1360 and died in 1419. He was viewed as a Robin Hood type figure, but of the high seas. Hiding in the caves and coves along this coastline and having knowledge of the tides, rips and rocks gave his rather modest ship and crew a huge advantage over the merchant vessels. He would surprise and attack hundreds of passing French and Spanish fleets, raiding them of their gold, fine wine, intricate fabrics, exotic food and fragrant spices to then share the takings with the people of Poole. Unfortunately, the French and Spanish grew tired of the attacks and together invaded Poole as payback, burning the town and killing hundreds of people, including Harry’s brother. Harry was away at the time, only to return to the devastation. Soon after the attack, a newly confident French ship sailed along the Dorset coast laden with the finest wine. Harry was quick to react, seeking revenge, raiding the vessel and capturing 12,000 gallons of the wine, leaving the wrecked French boat and crew to the mercy of the sea. Harry returned to Poole gifting the wine to the inhabitants. The whole town was drunk for a month and even today a Harry Payne day is celebrated every year in the town. His legend also lives on within Old Harry’s Rocks, the chalk stacks adopting his name, the caves below believed to have once been a hiding place for his loot.
From the Smugglers Inn in Osmington Mills, cycle up the village road, passing the holiday village and the equestrian centre, 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 famous for its White Horse, carved into the chalk hillside, in 1808, to honour King George III. King George’s health was deteriorating and was strongly encouraged to try sea bathing. The King and Queen both had faith that that fresh air and clear salty water was working and frequently returned to the welcoming town, often greeted with banners, flags and chants of ‘God Save the King’. The effects on the town were only positive, making it one of the most fashionable places to be at the time! However, legend says 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. The White Horse is visible inland, on the hillside to your left, looking down upon the villages of Osmington and Sutton Poyntz. The coastline stretches out ahead with the pinnacle of White Nothe, sticking out to sea in the distance – soon to be passed on the ride. Behind is the Isle of Portland and beyond, Chesil Beach disappearing to the west. When you reach the barn, there is a cross roads of tracks. Take the right hand option, downhill, gradually getting steeper as it approaches the road.
At the bottom, where you meet the A353 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 the guilty town of 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 of those 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 to your right. Pass through another gate and at the top you glide past White Nothe, the 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, circular cliffs of Lulworth Cove become more recognisable. Make your way through another gate in the dip to then rise again, the peak marked with a telegraph pole.
The views capture a huge expanse of the Dorset coastline. The peninsula of St Aldhelm’s Head is as far as you can see to the east, the Isle of 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 reach the top. It is then a quick run back down 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 the road, 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 Worbarrow Tout can both be seen. At the end of the track, meeting another road, turn right to ride down into the village of Lulworth.
Or you can turn right at Daggers Gate, following the road past the entrance to Durdle Door and the church designed by the young architect Thomas Hardy, before he became a writer.
Once at the bottom, where both routes combine, follow the road to the sea. Pass the Lulworth Cove Inn on your left, to reach the geologically unique cove. Its colourful twisted strata creates breath-taking scenery that, along with the entire route, is all part of the world famous Jurassic Coast – a UNESCO World Heritage Site.