The Headland Way is a stunning walk along chalk cliffs with a beach walk at either end. The route connects the seaside towns of Bridlington and Filey and passes close to the villages of Sewerby, Flamborough, Bempton, Buckton and Speeton.
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The first part of the Cleveland Way starts in Helmsley and after ten and a half miles, finishes at the visitor centre in Sutton Bank. The route climbs gradually out the wooded valley of the River Rye to reach the escarpment of the Hambleton Hills at Sutton Bank.
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This is the last section of the walk, finishing on Filey Brigg. It’s an easy walk of just under 4 miles. The route crosses farmland and then through holiday parks on the outskirts of Filey.
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The Centenary Way was opened in 1989 and was devised to celebrate the 100th anniversary of North Yorkshire County Council. The walk goes from York to the seaside town of Filey. The route crosses the Howardian Hills via Castle Howard and the Yorkshire Wolds via Wharram Percy. It links the Foss Walk in York with the Yorkshire Wolds Way and joins up with the Cleveland Way at Filey. It follows two rivers, the Derwent and Foss. The Wolds Way shares a lengthy section of the walk between Malton and Filey.
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Leaving Huskitt Hill, this 5.9 mile section of the Centenary Way goes through the Howardian Hills, an Area of Outstanding Natural Beauty (AONB). Most of the walk is through arable fields and woodland.
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Leaving Coneysthorpe this section of the Centenary Way heads towards the hamlet of Firby via Castle Howard. It is a stunning walk through parts of the Castle Howard Estate, the Howardian Hills AONB, arable farmland and wild woodland.
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This section of the Centenary Way crosses farmland at the foot of the Wolds escarpment before climbing back up to the Wolds at Staxton. The total distance walked is 5.7 miles.
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This section of the Centenary Way to Hunmanby covers 4.3 miles and takes you across typical Wolds farmland. The route offers some great views of Raven Dale and Camp Dale.
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This short section of the Centenary Way (3 miles) passes RAF Staxton Wold and then crosses typical Wolds farmland to arrive at Sharpe Howe, where you get a first glimpse of the sea and cliffs at Bempton.
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The route follows a clifftop path all the way to Filey Brigg. It’s possible to divert down to Cornelian Bay and Cayton Bay if you fancy some time on the beach. For much of the route, the path is very close to the edge of the cliffs. This the final (or first) section of the Cleveland Way and is a relatively easy walk with some beautiful coastal scenery.
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