July-August 2020
‘Are you okay sitting there?’
The woman, a middle-aged daughter, guides her elderly mother to a seat on the outdoor picnic table next to us. I expected several young families and collections of children exploring on these endless school holidays. They’re here too, but the Portland Bill café is dominated by the elderly, who are relishing their newfound freedom. This is Portland, Dorset, post-lockdown.

The staff speak politely into the tannoy. ‘Table number 112, your order is ready.’ I tip-toe over to the outdoor collection window at The Lobster Pot Restaurant. I have one hand in my pocket, grasping my mask in case it’s needed, while the other slips under the glass to fetch my scone and latte. I dodge the socially distanced queue on the way back, trying to work out how to make it to my table without breaching the one-to-two metre guidance.
Before us is an array of activity that I haven’t found in other seaside towns in this country. A dive boat hums past a fisherman in the open water. A group of horse-riders trot nearby. Walkers with poles hurry along the cliffs, passing resting people, who in turn are watching the birds flying overhead. Their dogs, large and small, curl up behind them, and photographers with better lenses than mine capture this scene: the red-white pristine lighthouse, and on the tip of this not-quite-island, the historical Obelisk. There is a small watchtower nearby, and through its windows I spot a lone man diligently spinning his telescope. Earlier, I watched kite surfers dance across the horizon at Portland’s entrance like they were swinging colourful flags of post-lockdown freedom. This is a giant adventure playground – but not everything is open. Portland Bill Lighthouse is still closed, although staff happily greet us in the gift shop and conjure a sense of anticipation about their upcoming, but unconfirmed opening date.
Earlier, I watched kite surfers dance across the horizon at Portland’s entrance like they were swinging colourful flags of post-lockdown freedom. This is a giant adventure playground – but not everything is open.
We are halfway through a self-plotted route around the perimeter of Portland using the OS Maps mobile application. This route is a way to see the best of the tied island. It takes almost four hours, but the photo-opportunities, lunch, swims, and the path detours can extend this to most of the day. Stops at attractions will make the tour last at least two days. For those wanting minimal social contact due to COVID-19, this day trip may be ideal if you live within one-two hours of Portland.
The Castle
The route begins at the 1540s Portland Castle, which was closed on our visit. The South West Coast Path, which is signposted at its entrance, begins on the opposite side of the road from the castle and winds sharply up the Jurassic Coast. This is the type of walk where cameras should remain firmly in your hands. Turning around often is advised to ensure the best views.

The Prisons
About twenty minutes, or just short of one kilometre into the route, the chimneys of the nineteenth century citadel poke out of the rolling hills. This is a massive citadel, turned prison, turned Immigration Removal Centre, turned prison again. The age and war-related history of the plot mean there are multiple listed and derelict buildings, which continue to attract urban explorers even as officials tighten site access. Scrambling up the short grassy hill above the prison offers panoramic views over the west coast of Portland. Here, it’s easy to see the residential areas sandwiched between sharp cliff edges, spreading in a triangular shape until either end seem to reach out to the gorgeous blue, temporarily calm sea.
There are still prisoners held on the island. Further along the route, I look up to see barbed wire curled along the top of the wall of the Young Offenders Institution. It’s odd to think that on the other side of the wall are people who cannot see the sailors or kayakers on the glistening sea, or the climbers and walkers who shuffle past.

Church Ope Cove
On the east side of the island, the ruins of Rufus Castle and St Andrews Church dominate the landscape of an otherwise quaint beach. The church ruins are nestled in a woodland that might be a little spooky at night, but it has the feel of a forgotten faraway place in the daytime.

Chesil Beach
After stopping at Portland Bill, the coastal path continues over the west coast and stays mostly cliffside. In this sepia landscape, sharp edges loom before us. Winding routes tempt us deeper into abandoned quarries and the innermost sections of the Tout Quarry Sculpture Park, which has surreal artistic designs.
The sun beats down on my calves as I cross the nearby wooden bridge. Sitting, I swing my legs over the edge, which is just set back from stomach-churning drops onto rocky bays. When I stand, the gentle breeze, adding to my sunburn, shifts the sediment under my feet.
Ahead of us is an arch that could be a window to another world as it reveals the great arm of Chesil Beach on the left, leading eighteen miles away. The grey and beige shades could be a white-sand beach, but it is made of tightly packed pebbles. What it misses in sand it makes up for in near untouched wild scenery, and we have so much of it to ourselves – well, us, and the finally free, sunlight savouring elderly.


The walk ends here on the beach, where it is worth catching the beginning of a promising sunset. We return to the starting point for the opportunity to visit the D-Day Museum and the Port. Finally, we take in the peacefulness of a port where the only sounds are of helicopters practicing take-offs and landings, and kayakers, who fish under the red sky.
How to Follow the Route
Download the OS Maps App, which includes a 7 day free trial. Follow this link to access the route.
How Long
Total distance: 15.46km
Time: 4-6 Hours
Suggested time in Portland: 2 Days
Suggested time for outdoor activities: 1 week
When to Go
Sadly, this trip will have to wait until coronavirus restrictions have relaxed and the weather improves. It’s worth the wait though, as more attractions will be open by then. It’s also a quick and easy trip to plan for those not wanting to plan any bigger trips in case restrictions tighten again.
How to Get There
It’s best to drive to the island. There are multiple paid parking zones around the island. A public parking area is next to the port, at the beginning of the route.

Other Things to Do
- Kayak around the island. Kayaks can be rented from £15 with Adventure 4 All
- To entertain the children, visit Fancy’s Farm, near the old prison. This is known for keeping rare Portland sheep, along with wallabies, donkeys, and many more. Entry is free.
- Take in a little more history at the Portland Mesolithic Settlement.
- Try your hands at climbing outdoors.
- When visiting in the future, look out for the upcoming development of Portland’s version of the Eden Project.
