The small market town of Helmsley is located near the River Rye on the southern edge of the North York Moors. Attractive stone buildings surround the Market Place and close by is the castle, making it a popular location with visitors. However, the Ebor Way turns its back on the Moors and instead heads south into the Howardian Hills, a relatively little known Area of Outstanding Natural Beauty that is a peaceful mix of gently rolling wooded hills, pasture, fields and parkland. The route passes close to Ampleforth Abbey and Castle Howard, a glorious 18th-century palace with landscaped grounds and gardens to match. This opening stage of the walk ends amid the attractive estate cottages of Hovingham, with its impressive Hall and church.

From the Market Place in the centre of Helmsley walk down Bridge Street and just before the bridge turn left along Ryegate, then right into Sawmill Lane. At the end the track turns right and at the next junction turn right and then left, on a broad track that becomes a riverside path. Eventually it reaches a gate, passing some yellow flag irises in a bog. Go through and bear left beside the meandering river. Cross a stone footbridge and continue on the riverside route.

On the far side of the field go through two gates for a track past a fish farm. Cross the river for a steady climb past Low Parks Farm. Join the farm access road, which crosses a wooded valley to a track just east of Sproxton.

The Ebor Way now turns sharp back left towards Throstle Nest. Pass through a wood and then turn right to follow the edges of the fields. Cross a footbridge, climb to a tarmac farm road and keep straight on uphill. Climb towards Oswaldkirk Bank Top, with a wide view opening up behind across Rye Dale.

At the road turn left for 0.5 miles (800m) and at Birch Farm turn right. Nearby there was once a village at Laysthorpe, but it had diminished in size even by the time of the Norman Conquest. Follow a farm track downhill, then cross the valley to the Cawton–Gilling East road on the far side.

Turn left, pass through Cawton, a hamlet of stone-built farms and cottages, and carry on along the track to Spa Villar, a large stone house set amongst trees. The spa was commercialized in the 19th century. Continue along the track into the village of Hovingham. Cross the second bridge over a stream and turn right past the church and the entrance to Hovingham Hall.