Cleveland Way Map and Itinerary

Arrive Helmsely— You can reach Helmsley easily by public transport.  Trains go via York to Malton and then you can take a bus to Helmsley from here.  See the travel section for more detailed information.

Stage 1: Helmsley to Osmotherley

Take time to wander around the historic village of Helmsley with its  picturesque old shops clustered around the market square.  The first highlight, Rievaulx Abbey ruins are worth the half a mile detour off the path, set in the wooded valley of the river Rye.  As you approach Sutton Bank the Kilburn White Horse—a limestone horse created by removing down turf can be seen.  The views from Sutton bank are wonderful and the walking easy with a few climbs as you follow the old drovers road to Black Hambelton.  The Days walking ends in Osmotherley, a quaint village with old pubs, shops and cafes. 

Stage 2: Osmotherley to Kildale

This is the most strenuous part of the walk,  like a giant rollercoaster walking up and down the Cleveland Hills.  The views are stunning across the heather clad moorland  and deep valleys to the south.  After Clay Bank Top a steep climb leads you to Round Hill and the summit of Urra Moor which is the highest point on the walk.  Walking across the moors provides for fantastic walking although watch underfoot as some of the paths can be boggy.  The path slowly descends to Kildale passing many burial mounds and boundary stones from the past.

Stage 3: Kildale to Saltburn-by-the Sea

The first part of the walk is dominated by the climb up Easby Moor to Captain Cooks Monument.  You are then given the opportunity to climb the eroded sand stone stump of Roseberry Topping.  The walk continues through farmland, woodland and a riverside path leads you to the coastal town of Saltburn-by-Sea where you leave the moors behind and prepare for cliff-top walking along the coastal section.

Stage 4: Saltburn-by-the Sea to Robin Hood’s Bay

From Saltburn the walk now hugs the coastline all the way to Filey.  You climb up Hunt Cliff and walk along dramatic sections, passing Rock Cliff (the highest point in the east of England).  The path then descends to the pretty village of Staithes with its fleet of Cobles (flat hulled fishing boats from Viking origin).  More dramatic coastal paths take you to Whitby with its picturesque harbour and town steeped in history.  High above the town are the remains of Whitby Abbey.  Following on past some small beaches and rock wave cut platforms takes you to picturesque Robin Hoods Bay.

Stage 5: Robin Hood’s Bay to Filey

The final stage of the walk heads through the seaside town of Scarborough,  where you pass busy beaches with traditional seaside entertainment, very different from the untouched villages you will have passed until now.  As you head down to Filey,  the final stage of the walk, look back at the vibrant colours from South Cliff and reflect on your walking adventure.  Filey is a busy little fishing village which has a good range of services for walkers.

Onward Travel—There are frequent trains from Filey via York to the rest of the UK.  If you need to retrieve your car form Helmsley then you can catch the bus from Filey or via Scarborough on the Moors bus.

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