A 2 mile circular walk around Nesscliffe Hill. An ancient fortress sleeps in the dark woods of Nesscliffe Hill. But that’s not all. Highwaymen, muggers and bandits once lurked among the trees and caves. Did Roundheads really have big, round heads?


2.0 miles


Hilly, can be muddy in places, unsuitable for pushchairs

Start from

Pines Carpark

Nearest to



Parking is available at the start from Pines Car Park

Map reference

Lat/Long: 52.7724784124, -2.9084292322

OS: SJ388198

The route

Lurking in the trees is an Iron Age hillfort that’s over two thousand years old. Back then all the trees would’ve been chopped down. The earth ramparts had high wooden walls on top. Hairy warriors could stand on them to lob spears and rocks at attackers. It’s thought that Oliver’s Point is named after Oliver Cromwell. He was the leader of the winning side in the English Civil War. His men were called ‘Roundheads’ even though they weren’t all baldies. Anyway, Cromwell probably didn’t come here. He had a lot on his plate overthrowing the king and taking his place. His army could have used it though. Some say they made round holes in the rock to secure their cannon. Can you find them?

Back in the days before telly people used to come here to drink tea and dance about. They even built wooden tents called pavilions to sit in. Not happy with holding tea dances, they built a maze and had competitions with bows and arrows. Sadly the maze and tents are long gone but this clearing is still known as ‘The Tea Tents’.

Kynaston’s Cave is named after Humphrey Kynaston, a real highwayman who used the cave as a hideout. His horse was called Beelzebub!

Highwayman Kynaston never needed a kangaroo for a steed. His horse Beelzebub was so good it once jumped the River Severn to escape the law. Kynaston even put its shoes on backwards to confuse people chasing him.