One of the most beautiful regions of Yorkshire is the North York Moors, known for its purple heather moorlands and the exquisite towns like Hutton-le-Hole and Thornton-le-Hole that are scattered throughout the countryside.
The first section of the Cleveland Way winds through this mesmerising rural landscape, taking you past ancient buildings, over stepping stones, and through twisted woodlands - and it begins in the charming town of Helmsley.
This route covers 7 miles and takes around 3 hours to conquer, although that will vary depending on the weather and how much time you spend taking in the beautiful surroundings, of course!
Section 1 - Rievaulx Bridge
This walk starts right next to Helmsley’s magnificent castle ruins and walled gardens, a must-visit for anyone staying in the area so ensure you stop by before you head off to Sutton Bank.
Begin at the Helmsley Castle Car Park where a sculpture with the iconic Cleveland Way acorn marks the very start of this 109-mile-long route. This guide only covers the first 7 miles but feel free to conquer the other 102 miles at your leisure!
Follow the lane out of town and, as the ground steadily rises, you’ll soon find you have wonderful views of Helmsley and the gardens to look back on.
At the end of the lane, turn left through a swing gate towards Blackdale Howl Wood. It’s an easy-to-follow track that takes you towards Whinney Bank, then down through Quarry Bank Wood before you meet the road that leads to Rievaulx Abbey.
If you have time, turn right just before Rievaulx Bridge to visit the magnificent Rievaulx Abbey. It was built back in the 13th century and thrived until the monastery there was suppressed in 1538. The spectacular ruins became a popular subject for Romantic artists in the 18th and 19th centuries and, today, is an iconic Yorkshire destination that draws visitors all year.
Section 2 - Kilburn White Horse and Sutton Bank
If you decide not to visit the abbey, you can continue straight across the Rievaulx Bridge to stay on the Cleveland Way.
Keep an eye out for cars as you follow along this narrow lane. Just after the road twists left, turn right off the road and onto a wide track that is signposted Cleveland Way / Cold Kirby 2mls.
You’ll come to a ford with stepping stones to cross. The water here is generally shallow, however, this is weather dependent.
After you’ve crossed the stream, continue through Flassen Dale and you’ll eventually come to a track on the right named Low Field Lane. This will lead you up a slope and into the charming village of Cold Kirby.
Pass the village church on your right and continue straight through the heart of the village until you get to Cote Moor Road, a track that will lead you over to the neighbouring hamlet of Hambleton.
You’re close to Sutton Bank! Cross the A170 and continue down the left-hand Cleveland Way trail until you reach the Sutton Bank National Park Centre.
If you want to take a detour and get up close to the spectacular Kilburn White Horse, cross the A170 at a minor junction and continue down High Town Bank Road. Turn right onto Low Town Bank Road, pass by the gliding club, and you’ll soon reach the beautiful Kilburn White Horse – however, we’d highly recommend seeing it at a distance for the full impact of this work of art.
Stay with us in the North York Moors
This stylish holiday home filled with pops of colour, clean lines, and simple white walls, is a wonderful place in the centre of charming Helmsley – perfect for a family of four and their canine companion too! Take the dog along on your travels and use this contemporary bolthole as your base while you traverse the beautiful North York Moors. Kids will love the bunk beds, and the wood burner and heated flooring ensure it’s a warm and welcoming space to return to after long walks.
Stay in Coco
This country cottage offers up a pretty place to lay your head during your travels. Welcoming up to six guests across two doubles and one twin, this could be just the place for a group of walkers to stay while conquering the first section of the Cleveland Way. Rest tired feet around the wood burner or enjoy al fresco dinner and a nightcap in the courtyard garden at the end of a long day.
Retreat to Rose Cottage
Stay in this superbly unique accommodation in Yorkshire for a one-of-a-kind holiday. A converted church and extension complete with fantastic original features (they have to be seen to be believed!) and comfortingly modern additions, four people can enjoy a wonderful getaway to this charming escape. There are two doubles so it’s ideal for a family or a group of adults looking for a retreat in Helmsley, two dogs are also welcome to stay with you so they can join you on a dog walk through Yorkshire.
Stay in a church
Discover more charming holiday cottages in Helmsley by searching through our collection - you’ll soon discover the perfect walkers' retreat!