From Milburn, go south east to Knock, then turn north eastwards, and follow the road past the "Christian Centre", all the way up the road to the top of Great Dun Fell. Before you get to the golf ball, turn off on the right, to follow the track down Trout Beck, across the Tees, and over the watershed to Tynehead. Follow the track/road all the way down to Garrigill. On the edge of town, double back onto the bridleway for the long climb up to Gregs Hut, then head down the other side into Kirkland. The track is quite vague and boggy in places to start with, but improves as you get further down.
If you really want to punish yourself/stretch the ride, you can cut out the climb to the golf ball, and go straight along to Dufton, and follow the Pennine Way up through High Cup Nick (well worth it for the views), all the way to Cow Green Reservoir. From there, take the footpath (yes, I know, but it's basically a road), north west around Herdship Fell. You can either go all the way along to the road, and down into Garrigill from there, or cut across the moors for about a mile, (not easy, but worth it to avoid the road), and then follow the tyne head track down.
If you're going exploring, check with the MOD before heading onto the tracks above Hilton, as you'll become an artillery target if you go at the wrong time…
