Sorry, yes. By Dukes Road, I mean the BW that runs west from Smallfield over Hobson Moss. From there, it’s heads SW towards Back Tor.
I recognise the second picture. My dog and I had a splendid time on that walk. Path from just south of Back Tor via Green Stiches and down to Walkers Clough if I’m not mistaken.
I was considering turning left at the point where Dukes Road is no longer a BW. On the 1:25k OS map, it’s says ‘High Peak’ and then heading generally west passed Cartledge Bents and Howden Dean.
Google Earth certainly makes it look like there’s a bit of a drop to the side in places and also backs up the quad bike thing. The bottom ~half looks like a fairly wide track. Big day out, old school XC is never a bad thing.
Probably best considered on a weekday but I’ve had some fairly good walks at the weekend by starting early so who knows