Hi jules -
Whitby is excellent and worthy of in depth investigation. If visiting the abbey, the church of St Mary’s nearby is worth a visit (as is the Whitby Tap pub also abbey adjacent). For a grand day out catch the bus to Robin Hoods Bay and after exploring the town walk back along the Cleveland Way to Whitby, if wet take the cinder path alternative route. Staithes and Robin Hoods Bay are similar places in my view, but if pushed to choose one over the other, I’d go with Robin Hoods Bay. Stuart is right though, Runswick Bay is a little known gem, but don’t tell everybody!
Speaking of the Cleveland Way, you can walk to Rievaulx Abbey from Helmsley along the Cleveland Way which is a short hike (I’m unsure of the public transport options back so you may have to make the return journey on foot as well) and the Abbey itself is fascinating. Helmsley is also worth a visit especially the castle, which I’ve visited twice recently.
If interested in monastic ruins, then Mount Grace Priory is worth a visit, it being a Carthusian monastery as opposed to the more usual Cistercian monasteries that thrived in this area (see also Byland Abbey, not far from Sutton Bank) and they had a rather different way of life to the Cistercians. Above Mount Grace and a short walk from Osmotherley, again along the Cleveland Way/Coast to Coast Walk is the lady chapel that was part of Mount Grace Priory. Its dedication to (unusually) Catherine of Aragon may have saved it from the ravages of the dissolution.
Something that needn’t detain you overlong is Sutton Bank, beyond the admittedly massive views over the Vale of York from the top. I recently stayed at the Fauconberg Arms in Coxwold not far from Sutton Bank. The village is charming and is notable for Shandy Hall where Lawrence Sterne (who was also the village cleric) wrote ‘Tristram Shandy’. Check opening times for the infrequent trips round Shandy Hall.
Similarly there isn’t much at Rosedale Abbey. It is the start of the ‘Hanging Stones’ walk, a six miles or so walk to a series of art installations by Andy Goldsworthy. However, prior booking is required - the thing gets booked up months ahead - as numbers are limited because the installations are in old farm buildings and each needs a key to unlock to gain access, they key being collected before setting off (route map/guide also supplied). Some of the hiking can be a little rugged, not to mention wet underfoot (not a problem lately!) but is well worth the effort. Beyond Rosedale are the industrial remains of the ironstone works and railway if that floats your boat, some accessed by the infamous Rosedale Chimney motor road climb. While in the area, don’t miss a chance to visit the Lion Inn at Blakey Topping, a pub sat in glorious isolation atop a moorland ridge.
Hopefully, if driving you can work out a driving route that will take you on a circuitous route to visit some a of these slightly off the beaten track places! If you need more information, please feel free to ask! Have a great trip!
Ian
