Lulworth Cove to Osmington Mills – Bike Ride

From the Lulworth Cove Inn cycle the chalk hills and absorb the sights along the Jurassic coastline to the Smugglers Inn. Climb out the valley to Daggers Gate, with its own little legend, to begin the rural route along paths of the original Customs Officials while they patrolled the cliff tops for smugglers. Pass Durdle Door, Bats Head and the slopes of Scratchy Bottom as the wide views stretch from St Aldhelm’s Head in the East to the Isle of Portland in the West. Skim the small settlement of Ringstead to descend and rise again to Coombe Bottom with views of the White Horse.  Cut through the small village of Osmington before following the narrow river valley to the coast and the Smugglers Inn.

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 Lulworth Cove Inn (Postcode: BH20 5RQ, Grid Ref: SY822800, What Three Words: hops.grunt.bulky). 

Map: OL15 Purbeck and South Dorset 

How to get there: From Dorchester, head South West on the A352, signposted for Wareham. At the Warmwell roundabout, take the second exit onto a dual carriageway. After just under 4 miles, at the junction marked by the Red Lion pub, turn right cutting through the small village of Winfrith Newburgh. At the church, follow the road around to the left and along the dry valley. Pass Daggers Gate and the turning to Durdle Door to head down the hill into West Lulworth. Follow the road around to the right to find the car park on the right and the Lulworth Cove Inn straight ahead.

Refreshments: The Lulworth Cove Inn at the start and the Smugglers Inn at the end. 

From the geologically unique cove, make your way back along the village road and turn left when it splits. Bindon Hill rises to the east, topped with earthworks of an ancient settlement, while on the opposite side, Hambury Tout towers with a lonely Bronze Age burial mound marking its peak.  Pass the church of Holy Trinity, designed with help from the poet Thomas Hardy, as he trained as an architect in his younger years. It was built to replace a medieval version that was no longer suitable for use come the Victorian times. However, remains of the graveyard still exist, deeper in the village.

Begin the climb up the hill, passing the entrance to Durdle Door on your left to then reach Daggers Gate. This ancient crossroads is believed to mark a witch’s grave. Her ghost is said to haunt the area and appears in the form of a hare. After her death, her own daughter, back in 1789, returned to this exact spot, not to wish her mother well, but instead to brutally murder Sam Varnell, a local farmer, stabbing him to death. It was this tragedy that gave the crossroads its name. 

Turn left onto the track, passing the farm buildings on your right. At the peak, the views stretch for miles, looking along the UNESCO World Heritage Site, part of the world famous Jurassic Coast, towards the Isle of Portland and Weymouth. Behind you the coast continues to the east to be met by the limestone peninsula of St Aldhelm’s Head. Head down the slope to skim past Scratchy Bottom and the Portland Stone and chalk rock formations of Durdle Door and Bats Head below. Scratchy Bottom was used as a location in 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.  

Make your way back up the slopes to meet a gate at a telegraph pole. Continue to follow the route running along the top boundary of the fields while the cliffs peak and trough down on your left. Cut between two large pyramidal shipping beacons, the tip of one only visible as the cliff drops to the sea, the other higher up the slopes and in the company of more Bronze Age barrows.

This old route, known as Daggers Gate Road was once much more utilised than it is today. Now, less popular than the coastal path, users are few and far between. However, it would have originally not only been the main medieval road between the coastal settlements, but also the patrolling paths of 18th century customs officers.

One of the most infamous of smugglers was Emmanuel Charles, who had complete control over the coastline from 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 the odd customs official. 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 well defended 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 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. 

Enter into the following field, gliding past the chalk headland of White Nothe on your left. Keep the boundary on your right as Chaldon Down sinks into the valley towards West Chaldon and Owermoigne, the old Down Barn being the only building clear in the landscape.  

Head through the next gate and onto a track leading down to Sea Barn Farm. Pass the thatched building on the left to then climb back up the hill and into the National Trust car park at Ringstead. The theme of smuggling continues in the bay below with Ringstead proving to be an ideal landing spot and the village being home for many of those involved. The smugglers would have kept in the shadows having the advantage of local knowledge.

The village of Ringstead used to be much bigger, thriving on what the sea provided but also its illegal activity. However, its downfall is suggested to have been due to the arrival of the plague in 1348, gaining entry through the guilty town of nearby Weymouth (Melcombe Regis to be precise). The village’s important trading links with the local and bustling, international fishing port meant that there would have been no escape for the residents. Today the majority of the village consists of earthworks, strip lynchets and scattered remains hidden down ancient tracks in the woodland. The old church has been converted into Glebe Cottage and the present buildings have more of a modern coastal retreat feel rather than medieval fishing village. Nevertheless, the peaceful location is one of the forgotten beaches along the Jurassic coastline meaning it’s a perfect place to escape the crowds who are attracted to more popular spots.

Despite its beauty there is danger too. Hidden under the water lie a number of shipwrecks. The King of Prussia (1753), Sally (1777) and Suky (1772) are some of the earliest recorded. At low tide the iron shell of The Minx rises above the water. In November of 1927, filled with coal, The Minx broke free from its anchor in Portland Harbour and, under control of the tides, was washed up on the Kimmeridge Ledges. The villagers were very warm that Christmas.

Follow the road along South Down, passing another collection of ancient burial mounds. Head down the hill and then up a short sharp climb to meet the A353. Turn right and, after about 200m and as the road bends, turn left through a gate to start another climb up the hill. The ground is not only steep but bumpy too, so take your time to then arrive at a crossroads of tracks at Pixon Barn.

To your right are the small village of Poxwell and its early 1600’s Manor house.  Poxwell Manor was another property that was touched by Thomas Hardy, but this time in a literary sense as he immortalised it as Oxwell Hall in his novel ‘The Trumpet Major’ (1880).

Turn left and through a gate, passing Pixon Barn on your right. Continue to climb and slowly the views reappear. The Isle of Portland reaching out into the English Channel, connected by the famous Chesil Beach that continues to run along the coastline westwards. Across the bay sits the Georgian façade of Weymouth. The town was made fashionable by King George who encouraged bathing in the sea as a means to wellbeing. Inland, the White Horse appears on the slopes, carved into the chalk in 1808 to honour the visiting King. However, the result was not what the artist or residents expected. Rumour has it that the King was so offended – with the horse representing him leaving Weymouth rather than arriving – that he never returned. Meanwhile, the artist’s story changes: it was said he was summoned to London and jailed in the Tower of London or he took his own life. Either way, it wasn’t a happy ending.

Remain on the track along Coombe Bottom and down into Osmington. Often forgotten in favour of its coastal sibling, Osmington Mills, Osmington is not only famous for its White Horse, but also for the honeymoon location for the Victorian painter John Constable. While staying here he painted scenes of the village that can now be found in museums.

At the village road, turn left to then meet the A353 for the second time. Turn left again to make your way out of the village and then take the next right, down the dead end road to Osmington Mills. Follow the winding lane, along the narrow valley, past the equine centre and the holiday village to arrive at the end of the road. The views open up for the last time towards the Isle of Portland and Weymouth, proving to be an idyllic spot, with origins dating from the 13th century. The pub is nestled next to a little stream just before it gushes into the sea, the steps on which Emmanuel Charles’ daughter was shot leading down to the thatched entrance. Its secluded and protected location, understandably a haven for smugglers.