The magnificent Cleveland Way takes you on an unforgettable moorland and coastal journey.
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As fellow walkers we understand the pain, and pleasure, that comes from long distance walking.  Almost a dozen long distance trails pass near our doorstep so we’re weary traveller, and muddy boot, friendly.  We’ve also a small, but perfectly formed, drying room in case you get unexpectedly caught in a shower.

Why not fill your boots on one of these spectacular trails starting, finishing, or heading through the heart of Helmsley.

The magnificent Cleveland Way takes you on an unforgettable moorland and coastal journey.

The Cleveland Way (109 miles)

Famously described as one of the UK’s most famous National Trails, the Cleveland Way,  takes you on an unforgettable journey through the heart of ancient Cleveland.  Running 109 miles between Helmsley and Filey Brigg the route skirts the North York Moors National Park.  Here you’re rewarded with a dramatic coastline and colourful heather moorland in one fabulous walking journey.  You’ll also be treated to fabulous castles, ancient stone crosses, fishing villages and some of the most breath-taking views in the country.

Captain Cook's monument on the Cleveland Way
Saltburn's iconic pier at sunset on the Cleveland Way

The Lyke Wake Walk (40 miles)

This famous moorland challenge was set up by Bill Cowley in 1955.  Cowley was a North Yorkshire farmer who suggested walking across England’s largest expanse of heather moorland within 24 hours.  Since first walked by Bill in October 1955, over 160,000 people have taken on the Lyke Wake Walk challenge.  The route traditionally starts from Sheepwash near Osmotherley (SE467992) and ends at Ravenscar (NZ981017).  If completed within 24 hours you qualify for the iconic coffin badge. Highlights include crossing a Roman Road, stepping stones over Wheeldale Beck, and if you’re really lucky you may spot a steam train on the North York Moors Railway

The walls of ancient Ebor (York) on the Ebor Way
The walls of ancient Ebor (York) on the Ebor Way

The Ebor Way (70 miles)

This relatively gentle long-distance walk stretches all the way from Ilkley right to the heart of Helmsley (or vice versa).   The trail takes its name from Eboracum, the Roman name for York, as you pass through the city whilst snaking through the charming low-lying vale of York.   Undulating paths take you over the Howardian Hills and if you link together the Ebor Way, Cleveland Way and Yorkshire Dales Way, you can walk non-stop for a whopping 310 miles.  Highlights of the trail include the rivers Foss and Ouse, the medieval walls of York, the charming Wharfe valley and the stunning stately home of Harewood House.  You’ll also climb up to the famed Cow and Calf Rocks on the edge of Ilkley Moor and discover lovely Wharfedale.

Filey beach where the Yorkshire Wolds Way meets the Cleveland Way

The Tabular Hills (48 miles)

We just love this wonderful introduction to long distance walking and from Scalby, just outside Scarborough, to Helmsley where the Cleveland Way begins.  The Tabular Hills Walk can be completed in just 4 days or provides a perfect add-on to the Cleveland Way.Highlights along the way include Hutton-Le-Hole, Keldy Castle and the spectacular Hole of Horcum, one of the most spectacular features in the National Park.  This huge natural amphitheatre is 120m deep and more than half a mile across.  The Hole of Horcum was created by spring-sapping where water wells water up and eats the rocks.  Once a narrow valley the landscape has now deepened into a spectacular cauldron.

The beautiful Ebor Way

Yorkshire Wolds Way (79 miles)

Takes you through an amazing chalk landscape all the way from the banks of the mighty Humber estuary to the dramatic headland of Filey.  If you’re looking for peace and tranquillity, lush green valleys, and forever skies, then this is for you.  You’ll find the start at the world-famous Humber Bridge, located just outside the city of Hull and, once the longest single suspension bridge in the world.  Almost 80 miles later you’ll arrive at the finish, in the coastal town of Filey, where you can join the Cleveland Way.  Along the trail and worth a visit is Kilnwick Percy Hall.   This historic place is a stunning Grade 2 listed building set within 42 acres of grounds with woodland walks, parkland and a lake. The Hall has been home to Madhyamaka Kadampa Meditation Centre for over 25 years and is a wonderful place with a World Peace Cafe serving lovely food in a relaxing location.  The centre is open to all and well worth a visit for lunch or cake

The Inn Way to the North York Moors (89 miles)

This is one of Mark Reid’s inn journeys which takes you on an 89-mile circular tour of the North York Moors from Helmsley. You’ll pass a number of inns along the trail which includes the heather-clad ridges of the central moors, lush valleys and picture-postcard villages. The walk is cut into six stages and based around the overnight stops of Helmsley, Hutton le Hole, Levisham, Egton Bridge, Rosedale Abbey and Hawnby before heading back to Helmsley.   This is a great walking journey if you prefer more self-navigation and less waymarking.

The Abbey Trail (116 miles)

This superb pilgrimage starts in Leeds and links seven stunning buildings – Kirkstall, Fountains, Byland, Rievaulx, Lastingham, Rosedale and Whitby.  This is one of the longest trails through Yorkshire and combines gently sloping hills, lush valleys, amazing views and some of England’s greatest abbeys.  You officially start at Kirkstall Abbey in Leeds and 116 miles later will arrive at Whitby’s atmospheric cliff-top abbey. Highlights along the way include Pateley Bridge, Ripon, Kilburn white horse, Helmsley, Hutton-Le-Hole and Grosmont.

Whitby Abbey on the Abbey Trail and Cleveland Way
Whitby Abbey on the Abbey Trail and Cleveland Way
Fluffy Herdwicks along the Cumbria way

The Cumbria Way (73 miles)

OK it’s not officially in Yorkshire but, as the lake district was once our home, we’ve included it here.  This wonderful walking journey takes you through the heart of the Lake District National Park.  You’ll follow tracks and paths along valleys and head over passes whilst surrounded by spectacular Lakeland scenery.  The trail links the two Cumbrian towns of Ulverston and Carlisle and highlights along the way include Coniston, Langdale, Borrowdale, Derwent Water, Keswick and the pretty village of Caldbeck. The trail is mainly low-level but does contain the stunning peak of High Pike. The magnificent Stake Pass takes you from one valley to another as you leave Langdale and head over into Borrowdale.  From Keswick the way continues to Caldbeck via Dash Falls or High Pike, and then follows the Caldew valley all the way to Carlisle.