We did the Tim Woodcock route this summer, we being me (a mountain biker) and 5 others, 1 of which actually does anything similar.
We took 5 days and, in all honesty, it was too short. I think if I had been on my own, or with a few guys as fit/experienced, we could have just about done without 12 hour days in the saddle, but the reality was we had very long days, only just making it on a couple of nights.
If you’re going to do it, I’d recommend taking your time a bit, particularly through the lakes as the scenery is incredible and the going is hard. There are a couple of road days in the middle where you can make up substantial time though.
We broke the days up:
St Bee’s – Eskdale (good)
Eskdale – Shap (waaaaaaay too long)
Shap – Grinton Lodge/Reeth (don’t stay in the Black Bull)
Grinton – Chop Gate (easy morning, tough afternoon)
Chop Gate – Robin Hood’s Bay (took direct route as potential mutiny was afoot)
Being stuck on a moor at 22:30 with 2 mechanicals, a bonkee and no distinguishable path was not fun.
We carried everything ourselves, though the others packed a bit heavy and sent stuff home from Shap.
I’d can’t recommend the New Ing Lodge in Shap enough, btw. Wonderful food and really great hosts with nice dogs.
It was fun, and I’d do it again, but with some more experienced riders.