Portland is “a bittersweet mixture of stunning beauty and rugged pockmarked rawness.” That’s according to Nick Fisher’s article in the Guardian about walking the Rodwell Trail. After passing Portland Castle, he begins “the long slow climb of Merchant’s Incline” up onto Portland:

“This flagstone, cut down the backside of the rump of rock that is the Island of Portland, follows the original railway that carried stone down from the quarries. The flags still show the signs of where years of ropes and cables and hooves rubbed and shaped the cold, grey stone.”

A good place is the 2km walk around the Portland Quarry Trails, described here on the Dorset Council website, which has some useful links to maps and leaflets.

“Follow the routes of the original horse-drawn tramways which carried wooden wagons, laden with stone, from quarries down to sea barges at Castletown. The trail explores contrasting quarry landscapes, old and new. It takes you under bridges, through tunnels and secret rocky gullies. It passes old horse troughs, quarrymen’s shelters, ancient fossil forests, hidden sculptures and abundant wildlife.”

If you fancy something longer, you could embark on a loop of the whole island, often called ‘The Isle of Portland Circuit, which Ronald Turnbull describes in his book Walking the Jurassic Coast:

“The walk follows the rim of the Portland slab, right around the island. At one point, below the Young Offenders’ Institution, it dips into the jumbly ground below the quarried cliffs”.

The 8 ½ mile walk takes in many of the highlights of the isle, including Rufus Castle, Church Ope Cove, Portland Bill and Pulpit Rock, and takes about 4 hours. There’s more information on making the full circuit of the island here, as part of the South West Coast Path. Or if you’re feeling lazy, you can sit back watch a film ‘A Walk Around The Isle of Portland‘ by Abbie Barnes.

A slightly shorter 7.5km circuit, starting and ending at Portland Bill, is set out by Edward Griffiths in Dorset Magazine. He also charts ‘A Walk Around Portland’s Quarry Tramways‘, which gives an insight into “this area’s fascinating social and economic history.”

If you wanted to focus on Portland’s lighthouses, you could follow the 5km walk described on the AllTrails website, or the 2.5km ‘Three Lighthouses Walk’ described by Teresa Ridout in Dorset Life magazine:

Old Higher and Lower Lighthouses were rebuilt in 1869 but had relatively short lives, eventually becoming inactive when Trinity House announced that both were to be replaced by the present Portland Bill Lighthouse at a cost of £13,000. The new lamp was lit for the first time on 11 January 1906.

The whole island, as Portland Town Council says, is “steeped in history and heritage with a landscape forged by its quarrying and maritime past, so it is an extraordinary place to take a stroll.”

Portland’s footpath heritage was celebrated in 2018 with the inspirational Portland Pathways Project, which aimed “to explore the histories of the footpaths, and rights of way, across the Isle of Portland”. The project was run by the filmmaker Bea Moyes for the b-side arts organisation, which is based on the island. She writes:

“I worked with an incredible group of local residents to explore local archives and collections, conduct field activities and walks to document the pathways, and record local memories of these ways.”

The fascinating report from the project ends on a wary note, drawing attention to the January 2026 deadline for UK councils to map unregistered pathways:

“… any pathways not mapped by that date will likely be lost. This deadline will likely reignite many debates over the official rights of way on Portland, with many pathways not officially recognised on the new Definitive Map ceasing to be maintained and protected by the Council. As this deadline looms, it is this ‘spirit of Portland’ which is perhaps needed more than ever, to protect and preserve the Island’s pathways for the future.”

For a shorter overview of the project, you can read the Portland Pathways Booklet, and the b-side website has some suggested walks on the island, such as the The Medieval Windmills Walk, which starts at St. George’s Church and ends at Church Ope, where you might if you’re lucky pick up a fossil or two.

John Vallins, writing in the Guardian, recounts a walk around the churchyard of St. George’s Church, which revealed “ranks of seemingly numberless tombs and gravestones leaning at varied angles, made of Portland stone, and most fashioned with elaborate carving, a tribute to the tradition and skill of Portland craftsmen.” The Tate gallery holds some fine photographs of the church, with the churchyard looking very overgrown, taken by the artist John Piper. And you can watch a BBC report on some recent conservation work at the church.

Looking north to Weymouth you can walk to the mainland via the Portland Railway Walk, which is outlined here on the website for Sandsfoot Castle & The Rodwell Trail. Julia Bradbury followed the Rodwell trail on one of her ‘Railway Walks’ for the BBC, which you can watch here. And looking further afield, if you’d like some company for rambling round the Jurassic Coast you can get in touch with South Dorset Ramblers.