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Views through a gate in a stone wall over the rolling green hills of Yorkshire, with its famous peaks in the far distance.

Walking Holidays in Yorkshire

Yorkshire is the ideal place for a walking holday, with a wide range of trails to choose from. This varied region boasts lush riversides, rolling fields, fascinating rock formations and plenty of welcoming towns and villages.

Find Your Holiday:

National TrailsThrough the Yorkshire DalesFewer MovesCircular ToursJust Passing ThroughBring Your Dog

Yorkshire’s National Trails

A ragged white underline

England’s National Trails are particularly well-waymarked and supported, with plenty of cultural relevance. Yorkshire boasts two!

Discover the Trails

Art in the Contours Holidays colours of a carved stone bench with a central upright, dedicated to the Yorkshire Wolds Way walking holiday in Yorkshire.

Yorkshire Wolds Way

  • 9-13 nights
  • 133 miles
  • Moderate to Demanding/Strenuous

Chalk fields greet you on the Yorkshire Wolds Way, a quiet and relatively unbusy National Trail that explores tranquil fields full of wildflowers and butterflies as it heads south to north along the Yorkshire Wolds.

Art in the Contours Holidays colours of a giant metal charm bracelet statue that can be found on the Cleveland Way walking holiday in Yorkshire.

Cleveland Way

  • 3-11 nights
  • 23-111 miles
  • Moderate to Strenuous

Take in the dramatic contrasts of the North York Moors and the Cleveland Heritage Coast on the Cleveland Way. This winding trail tours heather moorland, leafy woodland, windswept headlands and fishing villages sheltered in rocky coves.

Through the Yorkshire Dales

A ragged white underline.

The Yorkshire Dales National Park spans a huge area in Yorkshire, full of rolling hills, beautiful riverscapes and unusual limestone features. Tour these stunning landscapes on foot along these great walking routes.

Discover the Trails

Art in the Contours Holidays colours of Bolton Abbey, a large, fairly complete ruin with arched windows and framing towers that can be found on the Dales Way walking holiday in Yorkshire.

Dales Way

  • 7–10 nights
  • 79 miles
  • Easy/Moderate to Demanding

This stunning riverside walk winds through the lush greenery you might expect from the Yorkshire Dales, partitioned by drystone walls and softened by stands of deciduous trees. The Dales Way visits such sites as Bolton Abbey and Barden Tower, not to mention a host of characterful Yorkshire villages, and culminates in the southern Lake District.

Art in the Contours Holidays colours of a steam train crossing the Nidderdale Viaduct, an enormous brick structure that can be found on the Dales High Way walking holiday in Yorkshire.

Dales High Way

  • 6–10 nights
  • 90 miles
  • Moderate to Demanding/Strenuous

The Dales High Way climbs into the most dramatic stretches of the Yorkshire Dales National Park. It explores windswept moors and the intense limestone landscape at Malham, clambers Ingleborough and skirts Whernside, and finds a gentler conclusion in the Eden Valley.

Art in the Contours Holidays colours of a swan, commonly found on the lakes and ornamental ponds in the manor and castle grounds you'll explore on Lady Anne's Way walking holiday in Yorkshire.

Lady Anne’s Way

  • 6–11 nights
  • 100 miles
  • Moderate to Demanding/Strenuous

Try Lady Anne’s Way for the ideal mix of history and countryside in the Yorkshire Dales. The trail heads through market towns and historic villages along Lady Anne’s Highway, visiting a host of castles that starts with Skipton Castle and ends at Brougham.

Settle in with Fewer Moves

Ragged white underline

Make yourself comfortable and explore from just one or two overnight accommodations on these single- and twin-centre walking holidays.

Discover the Trails

Art in the Contours Holidays colours of sign for the Yorkshire Dales National Park mounted on a stone wall on the Yorkshire Dales Twin-Centre walking holiday in Yorkshire.

Yorkshire Dales Twin Centre

  • 6 nights
  • 52 miles
  • Moderate

Really settle into the Yorkshire Dales with this Contours Holidays exclusive format that involves a selection of great circular day walks from two overnight towns. Explore first from Settle and then from Malham to discover dramatic waterfalls and Yorkshire’s famous limestone pavement.

Art in the Contours Holidays colours of one of the top-heavy gritstone rock formations at Brinham Rocks, which can be found on the Nidderdale Way walking holiday in Yorkshire.

Nidderdale Way

  • 5 nights
  • 55 miles
  • Moderate/Demanding

Nidderdale lies just outside the Yorkshire Dales National Park but is just as beautiful, benefiting from the gritstone shapes of Brinham Rocks and the spectacular limestone ravine of How Stean Gorge. Drop into Ripley Castle to add a little extra culture to the trail, which functions as a single-centre tour with pre-paid transfers to and from the trail each day.

Circular Walks

A circular walking holiday is a great way to get much more familiar with a specific part of Yorkshire, linking local villages to the landscapes that support them.

Discover the Trails

Art in the Contours Holidays colours of Hardraw Force, a tall, thin, tumbling waterfall over a sheer rock face that can be found on the Herriot Way walking holiday in Yorkshire.

Herriot Way

  • 5–6 nights
  • 53 miles
  • Moderate/Demanding to Demanding

The Herriot Way is a circular walking holiday that explores the valleys of Wensleydale and Swaledale between some of Yorkshire’s most characterful villages, including Hawes, Keld and Reeth. It’s a brilliant introduction not only to Yorkshire but to long-distance walking as a whole.

Art in the Contours Holidays colours of Malham Cove, an enormous, ampitheatre-esque limestone formation found on the Three Dales Way walking holiday in Yorkshire.

Three Dales Way

  • 4 nights
  • 32 miles
  • Moderate

You’ll explore Wharfedale, Littondale and Malhamdale on this short yet dramatic circular holiday, perfect for a long weekend. Discover the limestone formations of Malham Cove and Conistone Pie alongside the rushing rivers Wharfe and Skirfare, not to mention Yorkshire’s famous welcome in Kettlewell and Malham.

Passing Through

These impressively long trails contrast Yorkshire with other counties along the way. Watch the British countryside transform from the rugged fells of the Lake District to the lush green expanses of Yorkshire’s countryside, or trek along the country’s spine through Yorkshire’s highest reaches as you strike north toward the Scottish border.

The Pennine Way

Art in the Contours company colours of a pointed monument up on the Pennine Way National Trail in Yorkshire.

On its long journey from Edale to Kirk Yetholm, the UK’s oldest National Trail cuts through the heart of the Yorkshire Dales National Park.

  • 15–22 nights
  • 21–265 miles
  • Moderate/Demanding to Strenuous

Coast to Coast Walk

Art in the Contours company colours of Wainwright's guidebook for the Coast to Coast Walk.

As it crosses England from St Bees to Robin Hood’s Bay, Wainwright’s famous trail delves through the Yorkshire Dales and North York Moors national parks.

  • 13–19 nights
  • 18–190 miles
  • Moderate to Demanding/Strenuous

Alternative C2C

Art in the Contours company colours of a train crossing the Ribbleshead Viaduct in Yorkshire.

The Alternative Coast to Coast Walk enjoys the Yorkshire Dales and North York Moors on its gentler ramble from Arnside to Saltburn-by-the-Sea.

  • 9–13 nights
  • 59–133 miles
  • Moderate to Demanding/Strenuous

Art in the Contours Holidays colours of three dogs - a beagle, a terrier and a sighthound - walking from right to left across the page.

Dog-Friendly Walking Holidays in Yorkshire

Several of our holidays in Yorkshire are available to walk with your dog, who’ll enjoy their own luggage transfers and pleasant overnight stays at your accommodation. Read more about how dog-friendly walking holidays work, or go ahead and choose from the following tours: