Anything involving the Lion Inn is usually good
A north-south or vice versa walk in the NYM is perfect for a night in the Lion actually, I did that a couple of years ago from Guisborough to Kirkby Moorside. Highly recommend it.
Despite being brought up right there, i have never actually walked the Cleveland Way completely. The North east coast is a favourite though...can be brutal this time of year however...
Any good walking ideas around Dalby/Cropton forest way?