From the smuggling coastline of Osmington, explore inland to discover pirate secrets in the nearby village of Osmington. Follow the River Jordan to Sutton Poyntz, in the shadow of Chalbury Hill fort. Visit the ducks of the village before climbing up to the chalk White Horse, there to honour a mad king. From the ridge, enjoy the impressive views across the stunning Jurassic coastline to then descend back to the village, with scenes admired, and painted, by the artist John Constable. Finally trace the footsteps of smugglers to return to the Pub
Distance: 7 miles/9km
Time: 3 hours
Total climb: 540 ft.
Max height: 450 ft.
Min height: 15 ft.
Terrain: Track, path, road and field.
Exertion: Medium. Some mud after rain and steep 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.
Dogs: On leads where livestock is present and in accordance with any notices on the walk and The Countryside Code. Refreshments frequently offered for them outside private residences both in Osmington and Sutton Poyntz, but don’t rely on this.
Osmington Mills was once a smugglers haven. Back in the 18th century the pub was run by Emmanuel Charles and was known as The Crown. He was the leader of a notorious smuggling gang that controlled this area of coastline, from Weymouth to Poole. He was often helped in his work by locals, gentry and even customs officers; however this did not mean he escaped trouble. On one evening he was nearly caught but only avoided capture by hiding in the chimney of the pub. His family was not so lucky; his daughter was shot on the steps outside. The chimney still stands in the centre of the building, the original flagstone floor also remains, where his, and our feet, now tread.
From the Smugglers Inn, turn right and head away from the sea on the village road. When the wooden signpost guides you to the left, follow it off the road to the next post. Fork right to then pass through a gate. Walk along the bottom of the field, ignore the next gate and head up the hill. Keep the field boundary and the Bronze Age Sandy Barrow on your right. When you reach the top, the views span wide over Portland Harbour and Weymouth town, often decorated with small white yachts from Weymouth Sailing Academy as well as large cruise ships from all over the world. Turn right through the next gate and stay on the track making your way to the right of the farm debris. To the north the views over Osmington become clear. The tower of St Osmund’s peeks out above the tree tops and the White Horse can be seen gracing the hill above. Follow the track around to the right and down the hill, making your way through East Farm to the road. Cross straight over to the pavement and turn left into Osmington.
Osmington is a small village often ignored, either due to passers-by on their route to Weymouth or those heading to the more well-known Osmington Mills; however Osmington is no less deserving of attention. Even John Constable spent six weeks of his honeymoon here in 1816. He painted vistas of the area – ‘Weymouth Bay’, which is exhibited in the National Gallery, and his lesser known ‘Osmington Village’.
Sticking to the pavement, follow the main road up the hill. It is narrow and busy so take care. Ignore the road to your right and continue straight on, passing the Old School House. When opposite Shortlake Lane, take the path on the right, following the tunnel of trees to the end. Go over a stile, enter into a field and keep your eyes peeled for a metal gate on your right taking you into the churchyard. As you pass St Osmund’s Church, you cannot miss the ruins of the old Tudor Manor House. Nothing but walls, windows and a small ancient doorway are what remain, but it is still an impressive sight. One previous owner was William Warham whose job it was to crown the young King Henry III during his time as the Archbishop of Canterbury.
Exit the graveyard via the old lynch gate, a place where the pallbearers would rest and shelter the coffin following a procession around the village. Or, in slighter older times, where the body would have been laid to rest, just dressed in a shroud, for a few days before the funeral. Turn left down the village road, heading past many thatched cottages and through a small crossroads. On your left you come to an old stone wall, which holds an intriguing secret. Osmington, being so close to the sea, may have its many associations with smuggling and pirates, but few villages can claim to have existing evidence of this. Hidden within this old wall is a small glass bottle. It lies vertically alongside the original stones. The story goes that it was laid to rest here containing an old map to treasure, or loot, buried somewhere in the hills around. Whatever it did contain was meant to be kept a secret and only those who knew of its existence knew where to look for it. Unfortunately, time and temptation got the better of the bottle and one day it was smashed and its contents exposed, so we will never know what secrets it once held.
Continue to head down the road and take the, slightly hidden, footpath on the left that guides you into the woods, steps helping with the climb. When through the woods, keep the boundary to your right, through the next field and over another stile. Turn right down a track and then left again to follow the footpath over a stile and into a field, minding out for horses.
It is along this footpath where you get the best view of the Osmington White Horse, high up on the hill to your right. With a date of completion at 1808, it was fashioned to honour King George III who frequented Weymouth for his mental as well as physical health. Bathing in the sea was a relatively new concept, mostly attributed to the poorer of people. Nevertheless King George was sure, and strongly believed, that it aided him. His visits to Weymouth helped the town immensely as the pastime of swimming in the sea gained increasing popularity throughout the late 18th and into the 19th century. However, the story continues. On seeing the newly carved chalk horse as he approached Weymouth, King George automatically took offence, the horse representing him travelling away rather than towards the town, wrongly assuming that the people wanted him gone. He immediately turned his entourage around and never returned. The artist himself was summoned to London and executed for his error, although alternative stories claim he took his own life. King George himself was growing increasingly unwell during this period and in 1810 he was finally confined to Windsor Palace, perhaps indicating at a different reason for him not returning to Weymouth. The Horse itself needs maintenance; the chalk regularly becomes overgrown with moss. The last cleaning took place in time for the Olympics in 2012.
Walk diagonally across the field, aiming for the next stile in the bottom right hand corner. Enter into a small yard, turn left, over a track and then straight over another stile. Head straight across the field again aiming for the bottom corner, next to the River Jordan (aka Osmington Brook). Climb over the stile, and between the large stones, into the next field. Here views of the rooftops of Sutton Poyntz come into sight. High above them sits Chalbury hill fort and tumuli, both of which providing clear evidence of ancient activity in the area.
Follow the valley, keeping the river on your right to cross a track and join another footpath. Go through a gate and fork right over the river. Follow the path around to the left to another gate and a bordered footpath, exiting onto the village road of Sutton Poyntz.
In 1902 a fire ripped through the village, destroying nearly all the houses. However, restoration took place in the sixties, resulting in the picture postcard village it presents today. Sutton Poyntz was featured as Overcombe in Thomas Hardy’s ‘Trumpet Major’ which was set in nearby Weymouth, during the Napoleonic Wars.
On entering the village turn right following the River Jordan up stream on your left. The river opens up to create a duck pond, opposite of which sits The Springhead pub. It is set in a beautiful location with the river banks surrounded by willow trees and filled with chatty ducks. Stay on the same road, ignoring the turning to your left, and then take the footpath on your right down White Horse Lane. Ignore all footpath diversions and continue going straight. After the first field, turn to your left and travel diagonally across, heading uphill directly towards the White Horse in the distance.On entering the village turn right following the River Jordan upstream. The river opens up to create a pond, opposite of which sits The Springhead pub. It is set in a beautiful location with the river banks surrounded by willows and filled with ducks. Stay on the same road and then take the footpath on your right down White Horse Lane. Ignore all diversions and continue straight ahead. In the large open field fork to your left and travel diagonally across, heading uphill directly towards the White Horse.
Once over the next stile you enter into rough woodland. Stay at the bottom of the wood, turning left when the path splits and the climb really starts. As you make your way up you are at the nearest to the White Horse but viewing it at this angle is difficult. On closer inspection you can make out its chalky legs etched into a steep canvas. Be careful with your footing though as the chalky path is slippery regardless of it being wet or dry. Take your time with it and enjoy the views expanding behind you.
At the top of the hill, you join a track where, on turning around, an appreciation for the far reaching views can be used as an excuse for a sit down and a rest. To the east you can see as far as White Nothe. Portland stands clearly out in the sea in front to you with Osmington Bay cradled by the island on its eastern side. Weymouth is also clear with its white Georgian architectural façade and sandy beach and to the west of Portland, Chesil Beach disappears off into the distance.
At the top of the hill turn right, ignore the track taking you back down the hill and stay on the ridge, views to the north appearing on your left. On reaching the masts, the views open up to the east and on a clear day the skyline of Poole can be seen. Continue following the track to Pixon Barn. Go through a gate and, looking left, you can view the village of Poxwell and Poxwell Manor. The manor is an imposing country house and, like Sutton Poyntz, had a role in Thomas Hardy’s ‘The Trumpet Major’ playing Oxwell Hall.
At Pixon Barn turn right and go through another gate. Once again, the views are extensive; Osmington Bay opens up in front of you and Portland sits higher in the sea. To your right you can view the White Horse and even see the footpath you have already taken.
Follow the track down the hill, it is easy to stick to and takes you straight down back to the village of Osmington. St Osmund’s church tower peeks over the trees in the valley below. Here you are faced with the same view that John Constable depicted in his painting ‘Osmington Village’, albeit slightly modified! Go through another gate and onto a bridleway, tunnelled by trees. When out on the village road, turn left to return to the main road. Turn left again, crossing when safe to follow your previous footsteps through East Farm.
As you cross the fields, once again the final views of the sea do not disappoint. The path undoubtedly used by many smugglers and officers alike, under cover of darkness and lit only by a lantern. Retrace your route back down the hill to return to the Smugglers Inn.