On our last visit to England we hiked several sections of the Cleveland Way. The Cleveland Way is a 109 mile (175 km) long-distance hiking trail that takes in parts of the North Yorkshire Moors and the North Yorkshire Coast. It starts in Helmsley and ends in Filey. When it opened in 1969, the Cleveland Way was the second long-distance trail in England, after the Pennine Way.

Helmsley to Rievaux Abbey

We hiked from Helmsley to Rievaulx Abbey on a drizzly day. Helmsley is a stately market town.

Wisteria on the facade of a hotel.

The houses and buildings in Helmsley are made of honey-coloured stone.

On the outskirts of Helmsley is a sign that marks the start of the Cleveland Way.

This way.

A short distance up the trail there was a good viewpoint back towards Helmsley and Helmsley Castle.

Hiking towards Rievaulx Abbey.

The trail went across a ridge and then descended into a valley.

Bridge across the River Rye.

Farmhouse in the Rye Valley.

Approaching Rievaulx Abbey.

Rievaulx Abbey was founded in the 12th century by Cistercian monks, who farmed in this pretty valley for 400 years. Like many other abbeys and monasteries, it was a thriving place. Then king Henry the 8th came along, the Donald Trump of his day. Henry was courting Anne Boleyn and wanted a divorce from his first wife, Catharine of Aragon, who had failed to provide him with a male heir. However, the pope refused his request for divorce. Peeved at this, Henry broke with the Catholic Church and declared himself the supreme head of the Church of England. Then, he went after monasteries and abbeys with ties to the Catholic church, ousting the monks, seizing their wealth, and selling off what could be sold off. Like other abbeys and monasteries in England, Rievaulx fell into ruin. Many outbuildings are now rubble but the main church is still standing, minus the roof.

Rievaulx Abbey.

After touring the ruins, we had a cup of soup and a cheese scone at the info center, and then we hiked back the way we came.

Sutton Bank

A few miles to the southwest of Rievaulx Abbey is Sutton Bank, an escarpment overlooking a vast plain between the North York Moors and the Pennines. The escarpment is thought to have formed during the ice ages, when glaciers scraped away rocks on the plain, leaving a 140 m high cliff of Jurassic strata. The Cleveland Way follows the top of the escarpment, offering superb views of the plains below.

Viewed from above, the English countryside looks like a quilt, with hedgerows stitching together the green sheep pastures.

We followed the Cleveland Way to the north for a few kilometers, enjoying the views. We then walked back the way we came.

Whitby

After Sutton Bank, the Cleveland Way makes its way northeast across the North Yorkshire Moors, and emerges at the coast at Saltburn-by-the-Sea. From Saltburn, the Cleveland Way follows the coastal path south to Whitby, Scarborough, and then ends at Filey.

We spent a week hiking the Yorkshire Coast while based in Whitby. From Whitby we hiked north to Saltburn-by-the-Sea in three stages, each time taking a bus to the trailhead in the morning and then back again to Whitby in the afternoon. I’ll describe our trip in this direction (northbound) even though it is counter to the usual direction (southbound). But let’s begin in Whitby.

Whitby is situated at the mouth of the River Esk, which is in a 100m deep valley. Above the town, on a windy headland, stand the remains of Whitby Abbey, a Benedictine monastery that dates all the way back to the 7th century. Like Rievaulx Abbey, the stonework of the main church is still standing. In the next picture, you can see the abbey ruins at the top centre, behind the church.

Narrow cobblestone streets surround the harbour, with pubs and inns once teeming with smugglers. Nowadays these streets are a magnet for tourists.

This pub was serving up meat pies with mashed potatoes, peas, and thick gravy. Yum.

We explored Whitby on a rainy day.

In the 19th century, Whitby became a popular seaside resort, and the Victorians built stately rows of houses on the slopes above the old town. We had rented an apartment in one of these houses for a week.

Whitby’s fishing harbour.

Whitby harbour entrance.

Continue to part two of the Cleveland Way.

Logistics

Helmsley can be reached by bus from York. We had a rental car when we visited Sutton Bank, but there is bus service. In fact it is possible to hike from Helmsley via Rievaulx to Sutton Bank, and to catch a direct bus from Sutton Bank back to Helmsley. (17 km hike, 10.5 miles).

Whitby can be reaches by bus or train+bus from York, Via Scarborough or Pickering. From Whitby there is good bus service up and down the coast. Bus X4 serves northbound destinations. Bus X93 Max and X94 serve southbound destinations. I used Google Maps to get departure times and locations.

  • Helmsley to Rievaulx Abbey is about 2.5 miles one-way.
  • Saltburn-by-the-sea to Skinningrove (highway bus stop) is about 4.6 miles.
  • Skinningrove to Runswick Bay is about 8.6 miles.
  • Runswick Bay to Whitby is about 8.4 miles.
  • Whitby to Robin Hoods Bay is 7.1 miles.

Highlights of the Cleveland Way, North Yorkshire, England