This is another one of my favourite walks, it’s only just up the road and has a bit of everything, it even has one of the best tea rooms at the half way point, which not only does excellent scones and toasties but some great bottles of beer too.
It works out at about 11 Miles depending which options you take along the route. Even if you don’t use this route you will see that there are loads of paths that you can take so use your imagination to explore some fantastic moorland.
If you’ve parked just outside of the town, head along the roadside passing the pub on your left, when you get to the wide track sign posted Roseberry Topping turn left and follow it, gradually climbing up to the woodland.
Once you reach the woodland you have a couple of choices as to which way to climb the hill, I like to either go straight up until I hit the paved path then turn right, following the path until it climbs up reaching the summit or to turn right and follow the path that leads up to the folly on the right hand side of Roseberry Topping.
Either way the aim is to reach the summit, once you have done so and enjoyed the views, head down the paved path at the back, which I think is the Cleveland Way, across Roseberry Common and up onto Newton Moor, once through the gate at the top, turn right and follow the path keeping the wall to your right.
Follow this path along Great Ayton Moor, until you reach the descent to Gribdale Gate, descent the hill and cross over the road, passing through the gate and follow the wide track gently up hill until you reach Captain Cook’s Monument.
Once you reach the monument turn left and follow the Cleveland Way through the woods until you reach the road at Pale End Plantation. Turn right and follow the road as it bends down hill through the farm, follow the road all the way under the railway bridge until you reach the cafe in Kildale, Glebe Cottage. It’s definitely worth stopping for refreshments.
On leaving the cafe you can either head back up to Pale End but go straight on to Lonsdale Farm then up to Nab end before reaching the track and turning left to head back towards Roseberry. Or you can go my preferred route and head along the road passing Kildale Hall on your left and the cricket club on your right.
Take the first road on the left and cross over the railway line, follow the path up quarry hill, past new row, a lovely little row of houses, go through the gate into the woods and follow the track until you reach the track at Percy Cross Rigg, turn left along here following it to the Edge of the wood at Hutton Moor, once you get to the wood, follow the path left to bring you back to the gate you will recognise earlier.
Now head down the hill, when you reach the bottom either skirt round to the left or right of Roseberry Topping unless you are feeling energetic and want to go back up it again. Either way you need to work your way back to the opposite side of the hill and to where you started your walk.