Oakdale Head​

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.

Oakdale Head map

The Lady Chapel

Or to give it its proper title: The Shrine of our Lady of Mount Grace. A peaceful spot, hidden away in a secluded wooded hillside outside of Osmotherley, The chapel is said to have been founded in 1397 was probably built for the use by the Carthusian monks of Mount Grace Priory. After the dissolution it fell into ruins but was rebuilt in the 1960s. Regular services are still held there.

The Lady Chapel map


Osmotherley in the rain, the village green, cross and 16th century stone table clear of people. A rare occurrence. The cross is a 18th century obelisk standing on a medieval stepped base.

Osmotherley map

Black Hambleton

The Tabular Hills make up most of the southern half of the North York Moors. Hills with a hard limestone cap. At 1,308 feet Black Hambleton is the highest point making it, for hill bagging enthusiasts, both a Hump and a Tump.

A Hump stands for HUndred Metre Prominence and is defined as a hill with a drop of 100 metres or more on all sides. On the other hand a Tump is a hill which is separated from adjacent tops by a height difference of at least 30 metres on all sides.

Thompson’s of Osmotherley

This shop in Osmotherley is in obvious need of a lot of care and attention. It was sold in 2013 after having being in the same family for over two centuries. Edward Thompson began selling groceries from his front room in 1786 when King George III was on the throne. The business grew and was passed on father to son for the next five generations. In 1910 it was described as “General Dealers, Tobacconists and Fancy Dealers etc.” and even blended its own tea by the name of “Jenny Brewster”, the name of a local spring. By 1935, the store was described as ‘a veritable mini Harrods’.

In 1943 with no son to take over it was left to Miss Grace Thompson to run the shop until a fall in 2004 forced her to retire. With no one to take over, the shop and all its fittings and contents were sold by auction in 2013. However Miss Thompson placed a restrictive covenant on the new owner that it has to be run as a shop and not converted into a house or cafe. This has the support of the town council and the National Park.

A note on the window says that refurbishment is planned. All the original shop fittings have been photographed and are in storage. A lot of work needs to be done.




Oakdale lies a mile or so south of Osmotherley. The long distance footpath, The Cleveland Way, goes down this path in the foreground and to the right of the reservoir in the distance. But if you last walked this route more than two years ago you may not recognise it for the reservoir has been substantially reduced in size. Yorkshire Water have spent £1.3m decommissioning it by removing the dam wall and landscaping leaving a small pond that will be managed for wildlife.

There were originally two reservoirs in Oakdale. The lower one was built in the late 19th century to supply water to Northallerton and district. Its water level was reduced in the 1990s and is now too a wildlife pond. The upper reservoir must have been built much later in the 1950s as it’s not shown on the OS Six-inch map published 1952. The photo was taken just above a spring known as Jenny Brewster’s Spring but who Jenny Brewster was I have no idea.

Fallen Boundary Stone, Scarth Wood Moor

Scarth Wood Moor, a National Trust property between Swainby and Osmotherley.