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, 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, off the road, follow it and then turn right at the fork, passing through a gate. Walk all the way to the end of the field and when you meet another gate, turn left, keeping 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, often decorated with white dots of small yachts as well as the larger white cruise ships. Turn right thorough the next gate and stay on the track making your way through some farm detritus. When the path turns to the left, 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 engraved into 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 road up the hill. It is narrow and busy so take care. Ignore the two roads to your right and continue straight on, pass the Old School House on your left and, when opposite the turning on the left, you arrive at a stile on your right. Climb over and follow the tunnel of trees to the end. Go over a second stile, enter into a field and keep your eyes peeled for a metal gate on your right. Turn through the gate to enter the churchyard. As you pass St Osmund’s church on your right, you cannot miss the ruins of the old Tudor Manor House on your left. Nothing but walls, windows and a small ancient doorway are what remain, but it is still an impressive sight. One previous owner was that of William Warham whose job it was to crown the young King Henry III during his time as the Archbishop of Canterbury.
Pass the large yew trees and 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. You may think nothing more of this, however it 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, it is not something easy to find accidentally. 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 held.
Continue to head down the road and take the, slightly hidden, footpath on the left that guides you into the woods. Steps help with the steepness. When through the woods, keep the boundary to your right, through the next field and over another stile. It is along this footpath where you get the best view of the famous 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 chalked carved horse when he next approached Weymouth, King George automatically took offence to 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.
Turn right down a track and then left again to follow the footpath over a stile and into a field, minding out for horses. Head diagonally across, 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 heading for the bottom right hand corner, next to the River Jordan (aka Osmington Brook). Climb over the stile which is next to an old tumbled down stone wall and into the next field. Here views of the rooftops of Sutton Poyntz come into sight. High above them sits Chalbury hill fort and on another hill, tumuli, both of which providing clear evidence of ancient settlement in the area.
Keep the river on your right and cross over a track to join another footpath. Go through a gate and cross over the river via a small, hardly noticeable footbridge. Follow the path around to the left and it brings you to another gate and a bordered footpath, exiting onto the village road of Sutton Poyntz.
In 1902 a huge fire ripped through the village, destroying nearly all the houses on one side of the river. 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. The pub is set in a beautiful location surrounded by willow trees and very chatty, rather expectant ducks, so if you want to make friends, bring some food for them! 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.
Once over the next stile you enter into rough woodland, even with a tree swing to take advantage of! Stay at the bottom of the wood with the fence on your right. Turn left when you come to a signpost guiding you up the hill and your climb really starts, the steepness probably making those with even slight vertigo end up with wobbly legs! As you make your way up you are at your closest to the Horse but viewing it at this angle is difficult. On closer inspection you can make out its chalky legs and you are able to appreciate what a steep canvas it is. 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.
Once 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. During stormy days and nights, this bay provides sanctuary for passing sea traffic so can sometimes be littered with huge cargo carrying vessels. On sunny days it is often full of small, colourful sailing boats from the nearby Portland Sailing Academy. Weymouth is also clearly seen with its white Georgian architectural façade and sandy beach. To the west of Portland you can make out Chesil beach as it disappears off into the distance to the far west.
At the top of the hill turn right, ignore the track taking you back down and stay on the ridge, making your way through a number of gates. On finally 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 all the way to Pixon Barn. Go through a gate and looking left, down the hill, you can view the village of Poxwell, Poxwell Manor dominating the scene. It is an imposing country house and, like Sutton Poyntz, had a role in ‘The Trumpet Major’ playing Oxwell Hall.
At Pixon barn turn right and go through another gate. Here you have another little climb but once again, at the top, 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 trace 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 out from the valley in front of you indicating that you’re nearing the village. Go through another gate and onto a bridleway, tunnelled by trees. Once out of the trees you are faced with the same view that John Constable depicted in his painting ‘Osmington Village’, albeit slightly modified! When back on the village road, turn left to return to the main road. Turn left again, crossing when safe to follow your previous footsteps back to the Smugglers Inn.
As you cross the fields, once again the final views of the sea do not disappoint, the path undoubtedly used by many, under cover of darkness and lit only by a lantern.