On the left of the photo is a small wood on a spur of pasture fields. Hard to see I guess but its name has always intrigued me since I spotted it on the map. Middlesbrough, just like the town further north on the banks of the Tees. The 1857 map names it, as does the modern map, so it’s been in use for a while. But did it acquire its name from the town or in its own right? The fields of pasture have been improved over the centuries by the application of lime and adjoined the Slapestone Inn, now a private residence known as Chequers. In the 17th and 18th centuries, drovers generally covered 9-10 miles a day with the herds of up to 300 cattle. The pasture fields provide a stance for the cattle where they could graze for a day or two before continuing on their way south to the markets of Malton and York and beyond. The drovers’ road was called Hambleton Street and is now tarmacked as far as Square Corner, the car park on the right.
A modern trail, the Cleveland Way, climbs Jenny Brewster’s Moor, the nearer ridge with the scattered trees to Square Corner crossing Oakdale Head before continuing south on the Hambleton Street.