4 Yorkshire walking challenges to try

Simon Edward • December 13, 2024

Hikers, assemble! Discover 4 Yorkshire walks that are challenging, varied and exceptionally beautiful.

In early 2024, Winning Moves UK released a new edition of Monopoly. Instead of taking your cheese around the districts of London, players now bought properties and landmarks in the Yorkshire Dales.

Look at the Yorkshire Dales Monopoly box and one thing jumps out at you straight away. Most of the pictures are from the great outdoors: cottages, hills and waterfalls. It's a far cry from the hotels of Mayfair and Park Lane.

The Yorkshire Dales, you see, is prime hiking country. With its unforgettable and varied scenery, it's the natural destination for hikers year on year.

And it's not just the Dales that have this pull. From north to south, from east to west, Yorkshire is perfect for a stroll.

It's also perfect for something a bit more strenuous. Whether you're raising money for charity or smashing a personal goal, walking challenges can be fun, healthy and, well, challenging.

In this article, we run through (walk through?) four of the best walking challenges in Yorkshire. So, grab your boots and pack your sandwiches – it's time to get walking.

1. The Yorkshire Three Peaks

The Yorkshire Three Peaks comprises a trio of well-known hills within the Yorkshire Dales National Park. Each year, thousands of hardy hikers come to tackle one, two or all three of the summits.

There's Pen-Y-Ghent, with its gentle incline turning into a semi-scramble. There's Whernside, with its view of Ribblehead Viaduct. And there's Ingleborough with its Iron Age remains.

Each peak has its distinctive character – but all have one thing in common. They all afford spectacular views of the Dales.

The three peaks can be combined in different ways. If you're in search of a challenge, you could try the 24-mile circular walk that takes in all three. But even a more leisurely walk limited to one or two of the peaks should be a satisfying challenge for most.

Picture of one of the Yorkshire Three Peaks.

As with all mountain hikes, safety is an important consideration. Springtime through to early autumn is the best time for walking to make the most of the daylight hours. Make sure you dress for the weather – and plan wherever possible so you get to enjoy those magnificent views.

2. The Lyke Wake Walk

"This ae nighte, this ae nights, / Every nighte and alle, / Fire and fleet and candle-lighte, / And Christe receive thy saule."

These words come from the traditional English folk song known as the "Lyke-Wake Dirge". The song describes the soul's journey from Earth to Purgatory and the hazards it encounters along the way.

By these standards, the Lyke Wake Walk is a doddle. But by earthly standards, it's a challenge and no mistake.

It was created by Bill Cowley in 1955. Cowley was a former Indian civil servant, North Yorkshire farmer, local historian, journalist and broadcaster. He set himself and his fellow walkers a challenge: to cross the North York Moors on foot from West to East within 24 hours.

The walk takes its name from the old coffin routes and ancient burial mounds in this area of Yorkshire. But despite these macabre overtones, it's a beautiful stretch of heather moorland – the largest in England, in fact.

A popular choice of walk in the 1970s and 1980s, today it's less well-known. But if you've got the stamina, it can be an unforgettable experience.

There's no official route, but templates exist. Make sure you follow them to avoid disappointment.

The sheer length of the walk means that training is essential – as are good-quality walking shoes and socks. Don't let blisters or sheer fatigue ruin the experience for you. Ouch!

3. Castle to Abbey: Yorkshire Coast Challenge

This 22-mile guided trudge undulates its way from Scarborough Castle to Whitby Abbey.

It's a gently dramatic walk, taking in gorgeous beaches, wooded glades, rugged cliffs and seaside towns. Popular with fundraisers and committed hikers alike, it gives you some of the most striking scenery in the region.

It's also a popular walk for wildlife spotters. Get lucky and you could see a dolphin fin, the flash of seal in the bays or sea birds in the air.

The walk is strenuous and suitable for adults only. No dogs are allowed except for assistance dogs.

4. Coast to Coast

No history of hiking would be complete without a mention of Alfred Wainwright, the legendary fellwalker whose guidebooks and illustrations are beloved to this day.

Much of his oeuvre focuses on the Lake District. However, he also devised a 182-mile coast-to-coast walk from St Bees in Cumbria to Robin Hood's Bay. Along the way, coast-to-coast walkers pass through three national parks: the Lake District, the Yorkshire Dales and the North York Moors.

For most of its history, the route has been largely unsignposted. In 2022, however, plans were unveiled to make it a National Trail. When completed in 2025, this could see a renewed interest in this legendary route.

Whether you do it as one unbroken journey or in sections, you'll soon see why it's rated as one of the world's great walks. Expect fells, valleys and villages in abundance.

Tradition has it that you should pick up a pebble and dip your booted toe in the Irish Sea. At the other end, you should do the same in the North Sea at Robin Hood's Bay.

Final thoughts

So, there you have it: four walking challenges you won't forget in a hurry. Each one is a testament to the many moods and landscapes of this gorgeous corner of England.

If you're hiking in the Grassington area, why not pay Stump Cross Caverns a visit? Our themed cafe is the perfect spot for a breather with its commanding views of the Dales. And whatever time of year you come, the caves themselves are a fascinating slice of prehistory. We look forward to meeting you!

Can't get enough of the stunning Yorkshire scenery? Check out our hand-picked list of walks near Grassington in North Yorkshire.

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