Isle of Portland

Split from the rest of the county, on an outcrop exposed to the mighty wind waves from South America, the Isle of Portland can be a harsh and dramatic environment. The landscape contains so many secrets with many more to probably still to discover. Explore the island, from the prisons to the cliffs and the lighthouse to the quarries, with the views never ending.

  • Distance – 8 miles / 13km
  • Duration – 4 hours.
  • Exertion – Medium.
  • Terrain – Path, track and road.
  • Dogs – Be aware of livestock and keep to the countryside code.
  • Map – OL Explorer 15 Purbeck and South Dorset
  • Start – Parking behind Portland Heights Hotel (Postcode: DT5 2EN, Grid Reference: SY689730, What Three Words: snacks.generally.whizzed)
  • Refreshments – Portland Heights Hotel and The Lobster Pot at Portland Bill.

The island is connected to Dorset by a single bridge and a 17 mile sand bank, known as Chesil Beach, linking it to the mainland at Abbotsbury. The Isle of Portland is sometimes called the Isle of Slingers, a name devised by Thomas Hardy. This is because the inhospitable residents were known to throw stones at any visitor attempting to enter the island. The quarries cast large scars across the landscape, but this mighty excavated Portland Stone has been sent across the country, and the world, to be used in construction of some famous buildings. These include St Pauls Cathedral in London and the UN building in New York. ‘Rabbits’ is also, apparently, a swear word on the island. This is thanks to the abundance of the furry animals, digging up miles of tunnels adding risk to the islands stability in addition to the quarrying.

The Island is so rich with tales, legends and mystery it requires its own encyclopaedia!

Parking behind the Portland Heights Hotel, set off to the east towards the Verne Prison. As you are at the highest point on Portland the views are spectacular – Chesil Beach disappears off into the distance to the west and Weymouth lies to the east of Portland Harbour. Portland is known for being a daunting place. The immediate landscape matches this with its sparse grassland, discarded rocks, unmanned quarries and the dark, grey prison. The Verne is cleverly hidden into the landscape both constructed underground and over ground.

When the road curves around to the left continue straight on and follow the smaller road around the hairpin bend. Walk past Fancys Farm, and its unexpected kangaroos, and onto the following track. When the path splits, take the left hand fork bringing you out to The Old Engine Shed and then to the large walls of Portland Prison. Walk around to the left, keeping to the road, the dominating walls rising high on your right hand side.

The footpaths guide you to the edge of the rocks turning to southerly direction. Quarry after quarry is walked through, scattered signs warning you of falling rocks and hidden holes, some sites working, some not. The views out to sea look over The Shambles, a shallow area consisting of a sandbank, hidden to shipping and is notorious for ship wrecks.  It was at this spot in 1805, where the Earl of Abergavenny was caught and sank, killing all 263 on board. Among those killed was the brother of the poet William Wordsworth, John Wordsworth, who also happened to be the captain.

Keep following the South West Coast Path signs to arrive at Rufus Castle. Rufus Castle is 15th century stronghold on private land, so cannot be explored. However, it can be viewed from below as the path from the main road takes you right under the castle bridge. Its structure has been hugely eroded and many pieces lie scattered around the landscape.

Continue straight on to reach Church Ope Cove, diverting down the left hand path to reach it. Church Ope Cove is a pebble beach, nevertheless one of the best in Portland, but there aren’t many! It would have been a perfect spot for smugglers to land and dump their contraband, probably trading with other neighbouring European smugglers too, under the watchful eye of Rufus Castle. It is underdeveloped so, other than the beach huts, there are few amenities; i.e. a water tap. It’s not an easily accessible beach either, but that is what makes it all the more special.

Head back up from where you came from, but turn left to enter into the ruins of St Andrews Church. All that is remaining of this 12th century church is a gable and a few of the walls, while, what dominates the scene, are the tombstones. Marked with skulls and crossbones; Pirates or victims of the Plague?! To leave the site, pass through the old arch stone entrance and up the hill, circling Pennsylvania Castle on your left to meet the road.

The pink building of Pennsylvania Castle was built in 1797 as a gothic revival mansion. Today it is a holiday let and has been used on a number of media productions including ‘Happy New Year Colin Burstead’ (2018) and ‘Made In Chelsea (2012).


Turn left onto the road and remain on it for just under half a mile. Just before you meet Southwell, divert off to the left, signposted, to re-join the coastal path. Follow it along the cliff edge, passing through a number of quarries with Portland Bill slowly coming into view ahead.

After only a short distance and reaching an old crane, turn right off the coastal path again, to investigate Culver Well. Once on the road turn left and Culver Well is on your right. This is an ancient Mesolithic site said to have healing properties! It is a hidden little gem consisting of a small waterfall covered in large stones. It must have at one time been a very important location for those that lived here thousands of years ago.

Once explored and back on the road head in the direction of Portland Bill that is now clear in the distance. Take the next footpath on your left. Heading though a collection of colourful beach huts.

On reaching Portland bill, you arrive at one of the most iconic sights of Portland, the large red and white striped lighthouse is a must see. Inside is a small museum and the opportunity to climb up inside. It is a very important active lighthouse, built in 1903-5. It is possible to walk right to the tip of the isle, marked by the Trinity House Obelisk, erected 50 or so years before the lighthouse.

Turn around to start your walk up the western edge of the island. Staying on the rocks, you meet Pulpit Rock, climbed only by the brave, and then fork to the right to enter into the car park. Head up the hill, passing the military establishment on your left and the coast guard buildings on your right. The views open up to the north exposing Portland’s harsh cliff edges and, if a clear day, Chesil beach can be seen disappearing into the distance.

The paths along this section can get very narrow but easy to follow, passing settlement and business along the way. On arriving at the second settlement, Weston, with the coastline slowly curving a little out to sea, is Blacknor. Here detritus of defences during the second world war still remain, including a gun emplacement and observation battery post.

The last leg of the journey takes you through Tout Quarry. Tout Quarry is another abandoned quarry but has become a dramatic sculpture park and it’s free. It’s scattered with odd features, carved out of the Portland limestone just lying around as well as a few old railway tracks.

Walk all the way through the quarry keeping the sea close on your left. Exit onto the main road, your starting view coming back into sight. Cross straight over and climb up the path that leads you back to The Portland Heights Hotel.

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