The 6 places measured earlier aren't too far from achievable in a single ride - GMaps makes it about 110 miles (
http://goo.gl/maps/X019q - not refined in any way). Helmsley is a bit off the beaten track though.
For the amusement value though, I will volunteer to ride with inflated space-hoppers on the pannier rails - they're high enough up there that they shouldn't touch down in even the most enthusiastic cornering.