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Walk The Cleveland Way On Your Next Visit To North Yorkshire

The Cleveland Way is a great way to explore North Yorkshire. Here’s our handy guide to walking the Cleveland Way.

One of our favourite things to do in the North York Moors is to simply walk! The Cleveland Way National Trail is a 109 mile (175 km) walking route that officially opened on 24th May 1969 it was the second recognised National Trail in England and Wales. The Cleveland Way is a route brimming with colour, life and sea views.

Cleveland Way

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Its abundance of heather moorland changes with the season, combine this with dramatic cliffs and views out across the North Sea. Amongst its many highlights are the ruins of Rievaulx Abbey and the Whitby Abbey that has looked down from above since the 13th Century. It is worth taking plenty of time walking the route because there is a great deal to see. 

Where does the Cleveland Way start?

The Cleveland Way starts from the attractive market town of Helmsley, most people walk the route in a clockwise direction from Helmsley to Filey as you are likely to have the wind behind you. But there is no right or wrong way and plenty of people enjoy walking the route in the opposite direction.

Cleveland Way Sign Post

The Cleveland Way heads across the inspirational, and breathtaking heather moorland of the North York Moors National Park, before reaching the coast at Saltburn-by-the-Sea. From here it’s a visual feast along the North Yorkshire coastline to Filey, passing old fishing villages and lively coastal towns. The National Trail runs through the famous smuggler’s village of Robin Hood’s Bay and the popular seaside resorts of Scarborough and Whitby.

Who can walk the Cleveland Way?

Cleveland Way Wall

Anyone who is reasonably fit can walk the Cleveland Way, however, the route is challenging in places so make sure you plan a route suitable for you. The Cleveland Hills and some of the coastal sections can be very challenging but this adds to the overall experience. Whilst the route is well-signed throughout, an up-to-date map or GPS mapping is essential. Comfortable footwear is essential and a pair of binoculars will certainly help you to see wildlife as you walk.

When is the best time of year to walk the Cleveland Way?

Cleveland Way Heather

You can walk the Cleveland Way at any time of year but if you want to see the moorland heather in bloom, the best time to visit is late August and early September. The best thing we find is that you don’t need to do the whole of the Cleveland Way in a single holiday. You can enjoy different sections at different times of the year.

Here are a few Cleveland Way walking routes…


Helmsley to Sutton Bank – 10 miles (16 Km)

For those visiting the area for a weekend or a few days, this section of the Cleveland Way is a perfect starting point and introduction to the trail. The walk is not too difficult, it climbs out of the Rye Valley to reach the Hambleton Hills escarpment at Sutton Bank. Starting at the market town of Helmsley you pass the ruins of Rievaulx Abbey, the managed woods and past the ponds at Nettledale, Hambleton Down racecourse and the enormous figure of the White Horse of Kilburn on this route. Finally, you can complete this trail with a visit to the Sutton Bank Visitor Centre where there is lots of information as well as guides, refreshments and toilet facilities.

Find more information and the full route here.


Osmotherley to Clay Bank – 11 miles (18 Km)

This walk boasts views of the Cleveland Hills, as well as north landscape across to Teesside and south and east into the moors and dales of the Park. Starting north out of Osmotherley this route takes you within half a mile of Mount Grace Priorynorth. Today this is managed by English Heritage and the National Trust and is totally worth a visit! On this route you will cross over 5 moors, Scarth Wood Moor, Live Moor, Cringle Moor, Cold Moor and Hasty Bank, try to spot signs of alum, jet and ironstone mining too. For refreshments, you can stop at Lord Stones Cafe at Carlton Bank before continuing on to admire the sandstone blocks which form the Wainstones. Continue along the route to Hasty Bank with its stunning views into the North York Moors National Park.

Find more information and the full route here.


Saltburn to Sandsend – 17.5 miles (28 Km)

For those who fancy going further, this route is a fantastic introduction to walking the North Yorkshire coastline as it falls within the designations of both National Park and Heritage Coast. Starting at Saltburn. On this route, you will climb up to Boulby Cliff. This is the highest cliff on the eastern coast of England at 203 metres (666 feet) and here you will see the Boulby Potash mine which is the deepest mine in Europe. You will pass through Staithes, which is stunning and there are plenty of places to stop here for a drink or bite to eat before you continue on to Sandsend. Wander along the beach at Runswick Bay before climbing the cliffs again. Your journey continues through to Sandsend where there is plenty of tea shops and pubs to enjoy.

Find more information and the full route here.


Sandsend to Robin Hood’s Bay – 10 miles (16.3 Km)

If you fancy a large dose of sea air and stunning coastal views this is a perfect walk for you. This section of the Cleveland Way takes you along some seriously impressive coastal scenery and you also visit the popular seaside resorts, Whitby and Robin Hoods Bay. Starting at Sandsend you quickly reach Whitby, you will pass Whitby Abbey then follow the clifftop walk to reach Robin Hoods Bay. In Robin Hood’s Bay, there are plenty of pubs, cafes, B&Bs and toilet facilities available so that you can stop and enjoy the charm of this village.

Find more information and the full route here.

Robin Hoods Bay

Robin Hoods Bay to Scarborough – 12 miles (19.3 Km)

This is a classic part of the Cleveland Way trail which heads towards Ravenscar and features the most incredible landscape and sea views. On this route, you will pass Hayburn Wyke and its beach, before spotting the view of Scarborough in the distance. Continuing on you will pass Boggle Hole and Stoupe Beck and as you approach Ravenscar you pass through the site of former Alum works, considered one of the first sites of the Worlds first chemical industry. You finish your route at Scarborough where you can enjoy Scarborough Castle and this wonderful seaside town.

Find more information and the full route here.

Historic Walking Guides Whitby, Robin Hood’s Bay, Runswick Bay & Staithes

Love walking? Love Whitby?

The Whitby Historic Walking Guide takes you on a tour of the town’s best, historic locations. Perfect for those who love to walk, explore, and learn about history. The guide is accessible for all reading abilities when it comes to history so don’t worry about getting a little lost in the jargon. This guide is so interesting, informative, and not difficult to read. You can buy it here. 

Ever walked any of these suggested routes along the Cleveland Way? Let us know in the comments.

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