A Dorset land agent has completed a 200 mile trek around 30 of the county’s Iron Age hillforts including ones in Purbeck, with his pack pony, Scarlet – despite getting lost in Wareham Forest on their way.
Roger Sewill finished the three week challenge on Tuesday 5th May 2026, arriving at Tolpuddle and completing a circuit of Dorset, raising more than £1,000 for Dorset Wildlife Trust along the way.
Time for a snack at journey’s end, under the 300 year old Tolpuddle Sycamore
Final push through Purbeck
The final push took Roger and Scarlet into Purbeck, following the Jurassic coastline after leaving Chalbury hillfort near Osmington.
Following stops at Bindon Hill, Lulworth, with ramparts enclosing a huge 272 acres, and Flowers Barrow, a hillfort built over 2,500 years ago above Worbarrow Bay, the pair made for Bovington Tank Museum to celebrate the role that ponies like Scarlet played in the history of warfare.
After that they headed for Wareham Forest, which hides Woolsbarrow hillfort, dating back 3,500 years to the Bronze Age, before finishing their journey by visiting Woodbury hillfort and Weatherby Castle, both near Bere Regis.
The walk, which began on Tuesday 14th April 2026 at Dorset Wildlife Trust’s new nature reserve at Lyscombe, was designed to raise money for the charity’s nature recovery work across the county.
Scarlet on the hills above Durdle Door, shortly before driving rain set in
Blown away by so much kindness
Travelling on foot with Scarlet, a rare breed Dales pony, Roger followed a route linking some of Dorset’s best known ancient landmarks, including Maiden Castle near Dorchester and Hambledon Hill near Blandford Forum – one of the best preserved Neolithic landscapes in Europe.
Roger had planned to camp in farmers’ fields with permission along the way, but was offered stables and shepherds huts at times, and said he was blown away by so much kindness from the people he met.
The walk was filmed as a documentary in collaboration with Bournemouth University’s media department, led by producer Shannon Marsh-Lloyd, a second year media student.
Roger also captured a photographic record of the Dorset landscape, which he plans to donate to local and national archives.
Roger and Scarlet had trained for the journey on Studland Heath, where they met some wild native breed ponies
“I took a wrong turn in Wareham Forest”
Roger Sewill, of Cheselbourne, Dorset, said:
“I promised the Bournemouth University film students the best view of the Jurassic Coast, including Lulworth Cove, if they joined me at the weekend, but I forgot it was a bank holiday, which of course meant rain.
“We all got soaked and at times could barely see which way to go, let alone the view, but Scarlet, the strongest of us all, carried some of the camera equipment and seemed to enjoy it the most.
“Then we left even further behind the high chalk ridges that Scarlet and I have become so familiar with, and found ourselves completely lost in Wareham Forest after I took a wrong turn.
“But I really loved the experience – I just let Scarlet walk ahead and followed her. We walked an extra five miles, because I didn’t want the moment to end.
“The journey had never really been about reaching a destination, but somehow, with over 200 miles covered, the end eventually found us.”
Media students from Bournemouth University have been filming the whole journey for a documentary
“Hiding in plain sight”
Roger added:
“I thought there were about 10 hillforts in Dorset and that it would be a nice thing to do to visit them all to see what lies between them, but when I discovered there were more than 30 hillforts in the county, my journey became a little more complicated.
“The hillforts were fantastic to visit, they have been in Dorset for around 3,000 years and they are still hiding in plain sight, even though all around them the landscape has changed massively.
“Before newspapers and canals, the pack pony would have been the bearer of goods and information across the country, so Scarlet and I have been retreading those paths.
“I can’t help but think we have experienced something quite similar to what it would have been like to travel across the landscape of Dorset thousands of years ago.”
The journey raised funds to support Dorset Wildlife Trust and its work to restore habitats, protect wildlife and strengthen conservation across the county.
At Osmington on the way towards Purbeck, where the white horse chalk figure shows King George III on a visit to Dorset in 1808
“Moving at a pack pony’s pace”
Roger Sewill said:
“As a land agent specialising in rural planning, the countryside is my workplace. Now with Scarlet, whose ancestors also worked the land, I undertake long distance horse hikes, linking places on foot – we are already looking forward to our next adventure!
“Travelling slowly between these iconic landmarks, which have stood for more than 3,000 years, we experienced the changing countryside and the communities that surround them.
“If you climb up to the top of, say, Eggardon hillfort near Bridport which commands the whole of west Dorset, you get the sense of why it was chosen to be there strategically.
“By walking the ridgelines you can see why people live in the valley villages, the paths where people would naturally have walked and a sense of how difficult it would have been for enemies to take them.
“Moving at a pack pony’s pace brings a deeper appreciation of the countryside and a reminder of how important it is to protect and restore Dorset’s natural environment.”
The weather was glorious for most of the three week journey around Dorset
Further information
- Donate to Dorset Wildlife Trust on Roger’s Just Giving page
- There’s a diary of Roger and Scarlet’s country journey on Instagram
