From the starting point at the Gribdale Gate car park the walk soon reaches Captain Cook's Monument on Easby Moor. From this viewpoint the panorama includes the village of Marton, where Cook was born. The site of his birthplace is set in a park, and an excellent museum is nearby. Two miles to the north west is the large village of Great Ayton. Across the plain to the south west are the Cleveland Hills, rising to 450 metres above sea level. From right to left the individual hills are Carlton Bank, Cringle Moor, Cold Moor and Hasty Bank, with Urra Moor, the highest point of the North York Moors to the south. To the north is the peak of Rosemary Topping, which we will come to later, and Great Ayton Moor.

Cook was educated, probably until he was 12, at the Michael Postgate School. It is likely that he learned to read at a dame school at Marton, where he added writing and arithmetic to the skills which he put to good use in later life. An outside staircase at the back leads to the upper story where there is the small but interesting Captain Cook Schoolroom Museum.

Airy Holme Farm became the Cook family home in 1735. Sheep and cattle would have grazed the steeper pastures while crops would have been grown in the more level fields that could be ploughed. In 1755 James Cook senior built a cottage in Great Ayton. The custom in this area is for the owners to incorporate their initials in the stones above the doorway. The cottage carries the inscription 'JG' with 'C' above, for James and Grace Cook.

The site of the cottage is now marked by an obelisk. The cottage itself was moved to Fitzroy Gardens in Melbourne, Australia, and re-erected in 1934 as part of the state's centenary celebrations. It was taken down brick by brick, each one numbered, and placed in 253 packing cases. Even the creeper growing along the sides of the house was shipped to Melbourne. The cottage is now one of Australia's top tourist attractions.

Unveiled on 12 May 1997 on High Green is a statue depicting James Cook at the age of 16 looking towards Staithes where, according to tradition, he first felt the lure of the sea. This was commissioned by Hambleton District Council and is the work of sculptor Nicholas Dimbleby.

Great Ayton's name derives from Old English Ea-tun, meaning 'river farm'. The watercourse flowing through Great Ayton is the River Leven, a tributary of the River Tees. A later addition of the word 'great' differentiates the village from nearby Little Ayton. Which is the small habitation visited and explored before arriving in Great Ayton on this walk.

The climb to the summit of Roseberry Topping can be avoided on this walk but that would be a shame; the viewpoint from the top of the 'Middlesbrough Matterhorn', as Roseberry Topping is affectionately known to the local population, is remarkable. Especially the view looking north across the sprawling expanse of Teeside's great town itself.

In 1736, when Cook's family moved to Airey Holme Farm and when he had time off from working on the farm with his father, young James took himself off up Roseberry Topping, which gave him his first taste for adventure and exploration, which was to stay with him for life.

The distinctive sugar loaf summit of Roseberry Topping can be seen from many miles away and was long used by sailors and farmers as a fixed navigational point. From Roseberry Topping it is a short walk along a stretch of the Cleveland Way National Trail back to the starting point of the walk.