I did it as last years big trip. I did an MBR route- St Bees to Robin Hoods Bay, 10 miles shorter than the Woodcock route its based on, but takes a more direct route over.
I carried all my own food and gear and rode it solo just under 3 days.
Very fond memories of that trip. I'll post some pics when I get 5.
I did it 2 summers ago and it was great fun. We were lucky with the weather and did it in the last week of a 6 week dry spell.
It took us 4.5 days self supported, staying in Youth hostels, and just carrying a few extra clothes for an evening, while the riding kit dryed out/got washed.
We followed Woodcocks route, although some of his bridalways are a bit optamistic.
Day 1 was catching the train up to St Bees, riding down to the beach and then setting off. The first 20 odd miles are easy and flat along an old railway line and along side Ennderdale Water. Then theres the push over Black Sail. I dont remember it being too bad, but thats maybe rose tinted glasses.
Its mostly rideable down the other side, and theres a pub waiting for you at the bottom. We stopped for a quick pint and then headed over to the YHA in Eskdale for the night.
Day 2 started off with another ride/push over the top of the next hill and across the first bog of the trip, through the forest and down to the stepping stones. Then its up and over Walner Scar. The decent has been resufaced but friends say its breaking up nicely again. Just give it another winter.
A few back roads and then you get to do the Loughrigg Terrace decent, which is fantastic if you get a clear run without any walkers. Over to the YHA in Troutbeck for the night.
Day 3 was up and over Garburn Pass, and then up and over Mossdale. Luckly for us the bogs had mainly dried out, but you'll get many more tails of when it wasnt. You'll also go right by the Bothy ifyou want to stop for a brew or strech out the first 2 days. First part of the journey where i felt like i was in the middle of nowhere as well. After that its over the M6 and a few country lanes into Kirkby Stephen. We stayed at the YHA there which is 'interesting'.
Day 4 A few more country lanes onto one of the non existing bridalways up to Tan Hill pub, and then down to Reeth. After this point accomodation becomes a bit sparce, and pretty much non-existant over the Moors, so we endened up staying at Stuarts at the Dales MTB Centre for some of of his great cake and for me to fix a broken spoke.
Day 5. Bit of a monster. Because accomodation is sparse we decided just to go for it and do the 90 miles across to Robin Hoods Bay. The bit between Reeth and Osmotherly is a bit tedious, through the flat lands of Yorkshire buy you just need to crank those 30 miles out. Up onto the Moors and the usual 4 seasons in an hour. Roasting one minute freezing cold the next.
Over to Goathland and one very steep climb back up to the top where you can see the sea over towards Whitby. Feels like you're almost there but you're not.
The end of the Woodcock Route takes somekind of longwinded route over to Robin Hoods Bay, but after 80 miles and a good 11 hours riding, we just found the shortest route over.
You then get a big fast road decent down into RHB, and you cant really see the sea until you're almost in it. The tide was also out, so a few more pedals to dip the wheels into the sea at the other side.
Plenty of bivi options but think you might struggle hammock wise.
The dales and moors don't have many forrests so your options would be limited, and there are a few long streaches where there would be no hammock options at all.