- Coming out of the car park at Wakeham, cross the road to take the footpath almost immediately opposite, alongside the wall of Pennsylvania Castle. Follow the signed footpath down through the woods, going through the archway into the ancient graveyard and Church ruins of St Andrew’s Church.
Pennsylvania Castle was built in 1797-1800 by John Penn, who was the Governor of Portland. His grandfather, William Penn, was a philosopher and Quaker who founded the Province of Pennsylvania in North America, also establishing the city of Philadelphia, today the USA's fifth most populated town. John spent 30 years enhancing his estate, sometimes controversially. In 1800-22 he fenced in the land around Rufus Castle and St Andrew's church (see below), but the public outcry led to a lengthy court battle, resulting in his paying five shillings rent per annum for it. He also had a large oval stone bath built above the cove, requiring his servants to fill it by hand with buckets of seawater; but this was also built on common land and the court set such an exorbitant rent for it (two shillings and sixpence per annum) that he abandoned it.
At St Andrew's Church look out for the Pirate’s Sarcophagus! It's not actually a Pirate’s Grave. The Scull & Crossbones carved into the stone was widely used as an ancient symbol for death.
A nineteenth-century archaeological excavation at St Andrew's Church found statues at the site of the old church similar to Bronze Age ones found at Salisbury, and another dig a century later found evidence that the site was occupied in the Iron Age. An ancient well and an earlier graveyard were also found, and it is thought that there was a Saxon church here around the sixth century, but the church dedicated in the fifteenth century to St Andrew was built by Benedictine monks sometime in the twelfth century, after an underwater earthquake had damaged the Saxon chapel a century before. In 1340, and again in 1404, French raiders landed in the cove and torched the church, which was rebuilt. In 1625 a landslip damaged it again, and half the cemetery fell onto the beach. A wall was built to shore it up but another landslip fifty years later caused a lot of damage, and in 1734/5 the Southwell Landslip sent more graves to the beach below, including that of the twin daughters of King Ethelred, who had both died at birth in 990. The repair costs this time were so high that, despite a visit by charismatic preacher John Wesley in 1746, the church was abandoned ten years later and a new one built at St George's Reforne. Some of the stone’s from the old St Andrew’s church were later used in local houses in Wakeham.
- From the graveyard follow the steps down towards the cove. Before you reach the bottom they join the main flight of steps to the beach from Church Ope Lane via Rufus Castle. Carry on down the steps to the beach, turning left before the sea to pick up the path heading through the undercliffs above the shoreline.
The rocks at the top of the cliffs are the Purbeck Beds, from the Lulworth Foundation (see the Lulworth Cove & the Fossil Forest Walk), with a band of harder Portland Stone below them. These rocks mark a gradual change in the environment in which they were laid down, from deep seas to coastal swamps. This happened while sea levels were falling at the end of the Jurassic geological Period, between 147 and 142 million years ago. As the sea got shallower, the sediments that made up these rocks were laid down in warm seawater, and like the rest of Dorset's Jurassic Coast they are full of fossils, including plants such as the fossilised tree outside the Portland Heights Hotel on Priory Road. If you examine some of the limestone blocks scattered around Portland, you will find that many of them contain shells and ammonites. All these rocks were formed in horizontal strata, or layers, but Earth movements caused by the continents of Africa and Europe colliding during a mountain-building period, known as the Alpine Orogeny, tilted Portland's plateau around 30 million years ago, resulting in its distinctive wedge shape.
- At Durdle Pier, about three-quarters of a mile further on, a wooden crane once stood at the water’s edge and was used to load Portland stone onto waiting ships. Sadly, the crane was washed away from the edge during storms in 2016. From a small stone quarryman's hut, the path heads steadily uphill to the left, to join the former track of the old railway. Turn right up here to carry on along the track for another half mile or so, to where a rusty post marks another path heading uphill.
Durdle Pier was built in the eighteenth century for loading quarried stone onto ships. It is said that the Portland stone used by architect Sir Christopher Wren to rebuild London after the Great Fire of 1666 was loaded onto the ships here. Like the red crane further south (see the Portland Bill Walk), the derrick crane that sat here was later used by fishermen for lifting boats into the water, after the quarries closed.
- Turn left onto this path and follow it up through the undercliffs, finally climbing through trees to the road at the top of the cliffs passing through a wooden gate. The ornate tall monuments that you can see here, are Victorian drainage ventilators.
The undercliffs along here were created by a series of landslips, the largest of which - the Great Southwell landslip - occurred in 1734, between Durdle Pier and Freshwater Bay. It was Britain's second-largest recorded landslide, and the area of remote wilderness that it created made it a haven for wildlife. Springs at the top of the cliffs soak through into the soil, and 10 British Primitive goats have been introduced to keep down the scrub with their grazing, which enables a rich variety of more delicate plants to thrive. Low-growing herbs such as wild thyme, small scabious and the tiny-flowered squinancywort flourish in the limestone grasslands, as well as the creeping plants horseshoe and kidney vetches and bird's-foot trefoil. These attract a wide range of butterflies and moths, including a species of silver-studded blue butterfly that is unique to Portland, as well as red-and-black Burnet moths that fly in the daytime, and the hummingbird hawkmoth, a European immigrant that really does resemble a hummingbird. There are also many species of rare lichens, liverworts and mosses.
- Reaching the road by the Young Offender Institution, walk along the Road to the south for a short while and follow the road around the corner to the right. This is a short diversion from the original route due to a short section of unstable clifftop. Keep following the road for around 20 yards until you reach the main entrance to the Prison on the right. Directly opposite the main Prison Gate, is the ‘Governor’s Garden’. The diverted route takes you through the main gate to the ‘Governor’s Garden’ and descend a couple of steps to follow a diagonal path that leads South Easterly. Continue along the path passing the Bowling Green on your Right. Head for the South East corner of the garden wall and exit out toward the top of the cliffs above Durdle Pier. Passing around the edge of Yeolands Quarry, bear left around Silklake Quarries beyond it to rejoin the Coast Path. Ignore the path to the right a little further on, following the Coast Path back to Rufus Castle. From here go through the archway and up Church Ope Lane to the main road, perhaps taking time to visit the enchanting Portland Museum. Turn left here to return to the car park at the start of the walk.
The Young Offender Institution started life as HM Prison Portland The Grove in 1848, when convicts working in the Grove quarries built their own cells (see the Portland Plateau Walk). Today it is a rehabilitation centre for prisoners aged 18-21.