I have just added this to the map of places to fly your drone at Drone Scene:
Land owner permission requirements unknown.
The Monument is served by Gribdale car park near Great Ayton Best time to visit I would say evenings as it can be popular for walkers etc especially at weekends.
The bonus for this location is that you can reach Roseberry topping from the same car park.
The originator declared that this location was not inside a Flight Restriction Zone at the time of being flown on 19/05/2022. It remains the responsibility of any pilot to check for any changes before flying at the same location.