Helmsley

Helmsley is the handsome one. A proper market square with a cross in the middle, a ruined castle standing over it on great banked earthworks, and a five acre walled garden tucked beneath the castle walls that dates from 1759. Add a run of independent shops and galleries that are actually worth browsing, and you have a town that carries a whole day rather than a quick stop. It also works as a base: Rievaulx is up the valley, Nunnington sits east, and the Cleveland Way National Trail starts here.

From Tea Time Cafe, take the A170 east out of Thirsk and up Sutton Bank. Stay on it through Sutton-under-Whitestonecliffe and past the Kilburn and Byland turnings, and the road brings you into Helmsley in about 25 minutes, roughly 14 miles. The long-stay car park on Cleveland Way is the sensible choice at around 6 for six hours, and it puts you next to the Walled Garden with the town a short walk uphill.

This is the one moors town with a direct summer bus. The seasonal Moorsbus M5 links Thirsk with Helmsley, which also makes it the interchange for Rievaulx on the M4. Its 2026 season ran on Saturdays, Sundays and bank holidays from 3 April to 27 September. Outside the season you need a car; check moorsbus.org for the next season's dates.

Do the castle first while your legs are fresh. The ruins sit on a huge set of banks and ditches, there is an interactive display on the site's history including its part in the Civil War, and the audio tour comes with the ticket. Then drop down to the Walled Garden, five acres of productive planting, orchard and glasshouses under the castle wall, which was used as a filming location for The Secret Garden. The Vine House Cafe sits inside the garden and is free to enter without a ticket. After that, the square and the side streets, where the shops and galleries are, and the start of the Cleveland Way if you fancy walking off lunch.

The Walled Garden is the one people underestimate and then stay in for two hours. It is a working garden rather than a display piece, it is fully wheelchair friendly, and picnics are welcome on the lawns. The castle earns its ticket on the earthworks alone, which are far more dramatic than the surviving stonework suggests from the road. And the town itself has kept its independents, which is rarer than it should be.

Wear sensible shoes for the castle, because it is a big site and the ground is uneven. If you are visiting the garden, the discount days are worth planning around: RHS members go free on Wednesdays, Gardeners' World members get two for one on Fridays, and CPRE members get two for one any day. Note the garden closes for winter on Sunday 20 December 2026, so the Christmas window is short. If it rains, this is one of the better bets in the area, since the glasshouses, the cafe and the town's shops all keep you dry. Combine it with Rievaulx in one loop and you have a full day; add Nunnington Hall instead and you have a gentler one. Fill up at ours first, because the drive over Sutton Bank is slower than it looks on the map.