Clearly it has to be Whitby. Bank holiday sunday night out in Whitby is an institution.
re post #2 The Cinder Track former Whitby to Scarborough railway is unsurfaced. Gravel bike or similar wide-ish tyres needed.
from Leeds I'd approach via York , Pickering, Dalby forest, brave a short ride on A171, and pick up the Cinder track by Boggle Hole YHA, to take you thru RH Bay and into Whitby.