Helmsley

Three miles north-west, signed off the B1257 down a steep hill into the Rye valley. English Heritage, around £12 adult, with a strong museum and a café. The soaring presbytery is the reason to come. Arrive after 3.30pm when the tour groups have moved on, or walk in from Helmsley on the Cleveland Way.

The castle is a two-minute walk from the square via Castlegate, with a dramatic split keep and deep earthworks, around £9. Directly below it, the five-acre Helmsley Walled Garden is a separately run charity with orchards, glasshouses and a good café — a further £8 or so, and the better of the two on a fine day.

Fifteen minutes west on the A170, at the top of a one-in-four bank that caravans are banned from. The National Park visitor centre has parking, bike hire and a café; the clifftop path to the White Horse takes about forty minutes return. James Herriot called this the finest view in England and on a clear day he was not wrong.

Helmsley's market has run since the thirteenth century and still fills the Market Place every Friday from about 8am to 3pm — produce, cheese, plants, fish from the coast and a fair amount of tat. Combine it with Hunters of Helmsley on the same square, an award-winning deli that will build you a walking lunch for under £10.

The gates are at the top of the square by the war memorial. Several hundred acres of parkland, a grass terrace with two eighteenth-century temples above the Rye gorge, and veteran trees that support a national nature reserve. Opening for the house and gardens is seasonal and limited, so check ahead; the parkland walks are the real draw.

Five miles south-west through Oswaldkirk. A working Benedictine community with a huge abbey church you can walk into for free, plus an orchard of 40-odd apple varieties and a shop selling their own cider and beer. The tea room does a decent lunch. Quiet, odd, and the antidote to a busy Saturday in Helmsley.

There is no railway. The nearest useful stations are Thirsk, 14 miles west on the East Coast Main Line, and Malton, 17 miles south-east on the York to Scarborough line; a taxi from Thirsk runs around £30. By bus, the 31X operated by Reliance runs from York to Helmsley in about 70 minutes, several times a day but with a last departure back to York in the early evening. The 128 crosses the moor edge linking Scarborough, Pickering, Helmsley and Thirsk over Sutton Bank. Driving from York takes 45 minutes on the B1363 or A64 and A170. In town, park on Market Place or the Cleveland Way car park behind it — a few pounds for the day — and walk; everything central is within five minutes.

If you want good dinners, a spa and the best-looking market square in the Moors, yes. If you are here to walk and drive out each morning, Pickering or Thirsk gives you similar access for £30 to £50 less a night. Helmsley's premium buys atmosphere and food, not proximity — Rievaulx and Sutton Bank are equally reachable from either.

Yes, and it is the best thing to do here. The Cleveland Way route runs about 5.5 km each way from Market Place, climbing through woods before dropping into the Rye valley by the abbey. Allow around 80 minutes one way plus time in the ruins. Boots rather than trainers — the descent to Griff gets slippery after rain.

The 31X bus from York is the practical option, taking about 70 minutes with several departures a day, but the last bus back leaves in the early evening so you cannot day-trip for dinner. From the north or south, take a train to Thirsk and a taxi for roughly £30. Once here, the town is walkable but the surrounding sights largely are not.

Most kitchens on and around Market Place take last orders between 8.30pm and 9pm, and hotel restaurants slightly later. On winter weekdays a couple of places close entirely on Mondays and Tuesdays. Book ahead for Friday and Saturday evenings all year — the town has more beds than covers and walk-ins get turned away regularly.