Yeah, the way I'd do it would be:
Ride through the night on Wednesday and into Thursday. Get train assistance from wherever that may be some time in the middle of Thursday to Barton-on-Humber (obvioulsy cycling over the bridge is essential) and stay there (or on the other side of bridge if time) Thursday night.
On Friday ride from Barton to Northallerton (or similar). Stay the night there.
Saturday a short hop to Tan Hill.
Probably way too sensible though