South West Coast Path
Today’s distance walked – approx 28 kms (17.3miles).
Ascent – approx 350m (1148ft).
South West Coast Path Day 39. I woke early but didn’t get going until around 8.30 am. The trail followed the last of the Fleet Nature Reserve towards Ferrybridge. I passed through a military firing range – no red flags today, so no detour needed. One of the huge holiday parks en route made a handy stop for a loo break and a sandwich.


The next 600 metres, an out-and-back detour down to the water, turned into a hellish tunnel of stinging nettles, and I got absolutely hammered. To make it worse, I suspect there was a higher, much friendlier path from the campsite, as I soon bumped into a couple I’d seen walking there earlier. Should’ve paid closer attention!

Ferrybridge to Portland
I reached Ferrybridge at 11 am. The gateway to the Isle of Portland, which technically isn’t an island at all. Over time, Chesil Beach’s vast pebble bank has joined it to the mainland. It’s worth a Google: 29km long, 200m wide and 15m high, it’s an incredible natural feature. Yesterday I mentioned broad bean-sized pebbles at the far end – here, they’re much bigger, and it’s strictly forbidden to take any.
The morning was overcast, and Portland looked a little dreary from a distance. I could see the Castletown area and the high stone cliffs that Portland is known for. Quarrying has taken place here for centuries. Portland stone was famously used to build St Paul’s Cathedral in London, and countless other buildings. The industry is still going strong today.
Heading into town, the sun made a welcome appearance and a scattering of little boats sailed across the harbour in front of me. The newer part of the marina was lovely, and from there I could see the lighthouse over in Weymouth, as well as the old breakwater stretching out to sea.


Castletown
I’d booked a cheap hotel in Castletown, directly in front of a massive, derelict block of flats – not exactly a beauty spot. (Portland’s YHA was fully booked – no rooms or camping, so if you’re planning to stay, book ahead). Fortunately, I was able to check in early and leave most of my gear behind before heading out to walk the island circuit. I left Castletown at 1.30 pm and headed around Portland in an anti-clockwise direction, heading down the west coast.
The guidebook described Portland as “very different”, and I’d agree. Quarrying has left its mark everywhere, and what must once have been a stunning natural landscape now feels heavily scarred. The trail began westward, past Tout Quarry and a sculpture park. There’s a short detour through the park to avoid recent cliff slips. Heading south and sticking close to the coast, I was rewarded with spectacular views back over Chesil Beach, the Fleet lagoon, and Weymouth Harbour.


The Path Around Portland
I didn’t enjoy much about the trail itself today – walking through such a broken, heavily quarried landscape. About halfway down the island, I passed the village of Weston, then continued to a large business park. A highlight, though, was spotting two kestrels hovering ahead on the cliffs to my right. I reached Portland Bill by 2.45 pm, marked by its unmistakable red and white lighthouse at the island’s southern tip.

The Mr Whippy Episode
I entered into a particularly British ice-cream debacle at Portland Bill. I’d asked the girl at the counter for a Mr Whippy with a flake, and she handed over an enormous tower of ice-cream, which I honestly didn’t think I could manage. The man behind me had just ordered five Mr Whippies, so I asked if he’d like to take my huge one and I’d get a smaller one. He said yes, so I handed it over to him and asked the girl for a smaller one.
By this time, another staff member was making the man’s five Mr Whippies and passed three more monstrous ones to him. He took them, turned to me and offered one. Then it all fell apart… Being British and painfully polite, I couldn’t say no, even though it was as big as the one I’d handed over to him. So I accepted the giant ice-cream, grabbed a spoon, and binned half of it (they really were ridiculously huge), thanked him, and walked off with my sensibly-sized ice-cream.
As I left, I turned back to thank the girl, who was trying to explain to her colleague that I wanted a small one. He finally made a small one, which ended up being the fifth Mr Whippy for the five-Mr-Whippies man, who was now reassuring the server that a half-sized one was absolutely fine. A perfectly British little comedy of manners and miscommunication. 🍦
Portland East Coast
On the return journey up the east coast, I passed a jumble of beach huts, many painted in darker tones, rather than the usual bright or pastel colours. As I continued through the broken landscape, I glanced east to the towering white cliffs that I’ll be tackling over the next few days. They looked both beautiful and brutal – it’s going to be a strenuous final stretch! I passed a small beach cove and gave the nearby 13th-century church a miss. I’m not sure why, but I was well and truly over walking by that point.

A little later, just below the prison, I passed a few people who were chatting about the route, wondering whether they should head inland to the left. We all said hello and I carried on. A kilometre later, I hit a dead end. The path was blocked at the beach! I returned, uphill, and realised I’d gone off-trail. The others had too. What I hadn’t noticed was that they’d been standing right in front of a sign pointing up and left for the coast path.
To Castletown
With an extra 2km under my belt, I climbed up and around the back of the prison, then followed the steep decline of the former Merchants Railway, dropping me back down into Castletown. There’s so much history around Portland that I haven’t touched on – from the castle built by Henry VIII to the huge Victorian fort. On another day, I’d probably have enjoyed exploring more, and I’m not quite sure why, but I just wasn’t quite up to it today.

