Helmsley Tours and Trips

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We offer 2+ tours in Helmsley having in total many customer reviews. Tour durations range from 12 to 12 days. Our Helmsley tours are offered by qualified and hand-picked tour operators and each Helmsley trip comes with a best price guarantee and no added booking fees.

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Discover our highly acclaimed tours in Helmsley, based on reviews and times booked.

The Cleveland Way

5.0(1 review)

The Cleveland Way walking trip is a 12-day journey through the varied landscapes of northern England, tailored for experienced and senior walkers seeking moderate adventure. Starting in Helmsley and ending in Filey, the trail combines rolling moorlands with the dramatic Yorkshire Heritage Coast. Explore historic sites like Rievaulx Abbey, the Captain Cook Monument, and Whitby Bay, famous for its fish and chips. The route, established as a National Trail in 1969, features a mix of tranquil farmland, forested patches, and charming fishing villages. The tour’s standout aspect is its seamless blend of coastal and moorland walking, offering both scenic beauty and a taste of local history.

12 days

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The Cleveland Way

A mixture of coastal and moorland walking The Cleveland Way. Walkers familiar with Wainwright’s Coast to Coast path will already be well acquainted with a couple of spots along the rolling Cleveland Way such as The Wainstones, Urra Moor and Robin Hood Bay. In fact it shares about 10 miles of routing with the ‘C to C’. Maybe they will be intrigued enough by their flirtation with the trail to don their boots once again and take up the challenge of the 110 mile Cleveland Way route from Helmsley to Filey in its entirety. What stands out is the experience of half a walk over hill and scarp edges and half along the hilly coastline of the Yorkshire seaside. There is much to enjoy for those interested in history, those ‘collecting’ National Trails and for aficionados who wish to enjoy arguably the best Fish ‘n’ Chips in England at Whitby Bay! This is the second of the ‘National Trails’, dating from 1969 and is rooted in the North York Moors National Park / Yorkshire Heritage Coast. Along its length there are contrasts in walking between field - quilted farmlands, forest patches, dramatic sandstone rock scarps, bleak moorlands and the highly eroded coastline, punctuated by beautiful little fishing villages, clinging to the cliffs. It is an area that has been threatened by the expansion of the Tyne – Tees Conurbation on the one side and by the encroaching North Sea on the other. However apart from busy coastal towns such as Scarborough, it remains a tranquil area, bolstered and protected by the presence of the National Park of which about 80% of the walk occupies. Highlights of the Cleveland Way include, the remains of the Norman Rievaulx Abbey, and 13th century Whitby Abbey (but dating from the 7th century!), the Captain Cook Monument and Robin Hoods Bay with it's cliff-hanging cottages. Most of the route follows well sign-posted footpaths, which generally have good surfaces and are easy to follow. The exception to this is along the coastal path, which, in some places, is overgrown and uneven underfoot. The amount of daily ascent and descent is moderate, with much of the walk being on level or gently sloping ground. There are a number of steep ascents along the section from Osmotherley to Urra Moor and at some places along the coast, but these are generally of no more than one or two hundred metres at a time.

12 days

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