I did it in a day a couple of years ago – long day but really worth it.
I was on a road bike and my riding partner was on a Salso HT with slicks. Weirdly, he was the only one to get punctures, just out of Whitehaven.
Everything was perfectly possible on the road bike – we took the road down from Whinlatter to Keswick (where second breakfast was taken) and (I) pushed up the Rookhope incline (after tea at the the Rookhope Inn).
We did have another friend join us for the final leg at the Rookhope Inn – that really helped inject a bit of pace, where I think we would have struggled. Well worth trying to get someone to volunter if possible – 40odd miles from there but one you are over the incline, you can see the sea…
There were a few "shady characters" hanging around the tracks as we were coming through Consett etc – no problems but did put me a little at unease!
Oh yes – the Hartside Café wasn't big on veggie stuff, I seem to rememeber…
Good Luck and enjoy!
Rachel