The Old Hall in North End was bought by Lady Juliana Walmsley in 1665, for the use of Franciscan Friars. They were forced to leave in 1832, but returned in 1969. The top floor is now a lovely Catholic Church, entered through the garden. The friars served pilgrims visiting the Chapel of the Lady of Mount Grace, which stands on the hilltop outside the village. It was built by Carthusian monks from Mount Grace Priory early in the 16th century, on the site of an earlier shrine and rebuilt in 1960. The large well preserved ruins of the priory, which was founded in 1398, are at the bottom of the hill to the west of this walk route.

As you head north out of Osmotherley you gain height on the walk along Ruebury Lane. At Ruebury Hill there are tremendous views to the west, looking across the pan flat expanse of the Vale of Mowbray. Beyond the vale are the easternmost hills of the Yorkshire Dales. A little further on, you pass a microwave radio station, 982 feet above sea level, which receives and transmits television and telecommunication signals.

The next stretch of the walk crosses open moorland. Red grouse, wheatears and curlews may be spotted here; while adders and common lizards, though not often seen, live among the heather, bilberry and bracken. Hares are a common sight as you cross the open hillside. Soon you turn right and drop down the hillside to arrive at the north end of Cod Beck Reservoir.

Cod Beck Reservoir was created for the Yorkshire Water Board in 1953. A stone quarry was submerged along with a group of cottages at Wild Goose Nest, where there was once an illicit still. You head across open moor on to an old straight track through a conifer plantation. Green Lane, bordered by honeysuckle, rowan, dog roses, hawthorn and gorse descends gently out of the trees.

Once clear of the trees and onto open ground there are good views of Osmotherley opening out to your right. Around this point, the route turns off to follow the Cleveland Way. This, Britain's second longest long distance path, is a well way marked route that runs 93 miles around the moors from Helmsley to Filey Brigg on the Yorkshire coast. You cross Cod Beck and continue through woodland to the arrive back in Osmotherley.

Osmotherley has connections with John Wesley, first invited here in 1745 by Peter Adams, a former Franciscan Friar. The Methodist Chapel in Chapel Passage, built in 1754, is one of the earliest non conformist chapels in England, and is still in use today. Wesley often preached there, standing on a stool to make up for his short stature. The stool can still be seen in the chapel.