The Cleveland Way National Trail is a 109 mile (175 km) walking route through beautiful and ever-changing landscapes and scenery. It starts at Helmsley and ends on Filey Brigg. The Trail offers the best of both worlds in the region, heather moorland, and stunning coastal scenery. This short break offers three circular walks from the start of the route in Helmsley with options to visit attractions such as Rievaulx Abbey, Duncombe Park, and Helmsley Castle. 

2 - 4 nights Available on request Helmsley, England

Getting to Helmsley

By Rail: Thirsk is the nearest mainline station to Helmsley, with regular trains running from London, covering the journey in around 3 hours. Fast through-trains run from most other parts of Britain.  Thirsk to Helmsley is a short taxi ride. 

By Car: The area is served by excellent roads. The A1/A1(M) motorway provides fast, easy access. From the North take the A68 cross-country 'holiday route' through Northumberland and Border Country. From the West, the A66 provides a scenic cross-Pennine route from the Lake District and M6 motorway. 


Hotel Category

B&Bs, Hotels and Inns (3*)

Grade (Difficulty)

This grade of this tour is easy to moderate.

Start Location

  • Helmsley

End Location

  • Helmsley

Daily Distance Range

  • Walking–Minimum: 6.5 miles / 10.5 km Maximum: 8.5 miles / 13.8 km

Duration (Nights)

This tour has a variety of durations from 2  nights to 4 nights. 


This tour is available from January until December.

What we'll give. What we won't

What is included in the tour

  • Bed & Breakfast Accommodation
  • Fully comprehensive tour pack with colour coded routes on local maps
  • Emergency Telephone Assistance
  • Smart Phone GPS App with Routes

What is NOT included in the tour

  • Meals Except Breakfast
  • Transport to and from Helmsley
  • Tips

Arrive Helmsley and stay overnight.  

Helmsley is the only market town in the North York Moors National Park, and is the perfect base for enjoying the wider area. There’s plenty to do in the town, from fascinating attractions including the National Centre for Birds of Prey, Helmsley Castle, Helmsley Arts Centre and the Walled Gardens, to award-winning eateries and the town’s very own Brewery. 

A: Circular route from Helmsley via Rievaulx Abbey (7 miles / 11.2 km) 

There cannot be a finer start to a National Trail than the delightful market town of Helmsley, centred around a historic market square. Helmsley Castle is clearly visible as you start to climb out of the town. 

The route from the market town of Helmsley to Rievaulx Abbey is a well-trodden one, but it never loses its capacity to delight and inspire. This 7-mile circular route climbs gently for sweeping views of town and castle before dropping down through charming bluebell woods to reach the peaceful village and tranquil ruins of Rievaulx Abbey. From Rievaulx Abbey, return the same way back to Helmsley. 

Stay overnight in Helmsley.  

BCircular route from Helmsley via Beck Dale (6.5 miles / 10.3 km) 

A circular walk from the market town of Helmsley in Ryedale. The route heads north through the beautiful woodland belt of Beck Dale, following an idyllic babbling brook, before crossing a few fields and returning via another woodland belt, Ash Dale. 

Stay overnight in Helmsley.  

CCircular route from Helmsley (8 miles / 13 km) 

A circular walk from the market town of Helmsley in Ryedale. The route heads out across sheep pastures and open fields to explore the woodland ravine of Riccal Dale, in the company of the beautiful River Riccal. 

Stay overnight in Helmsley.  

Depart Helmsley after breakfast the following morning. 

Places of interest 

There are a variety of places to visit along the route.  We have picked out the highlights and can arrange entry / tickets for customers as required. 

Rievaulx Abbey 

Discover the impressive ruins of one of England's most powerful Cistercian monasteries. Uncover the fascinating past and the lives of the monks who called Rievaulx Abbey their home. Explore our elegant museum displaying previously unseen artefacts which tell the story of the rise and dramatic fall of the first Cistercian abbey in the North of England. 

Helmsley Castle 

Unlock 900 years of life at Helmsley Castle, a must-see for any visitor to the picturesque market town of Helmsley in the North York Moors National Park. 

Discover how the castle evolved over the centuries, from a mighty medieval fortress to a luxurious Tudor mansion, to a Civil War stronghold and a romantic Victorian ruin. 

Helmsley Walled Garden 

This historic 5-acre walled garden has vibrant displays of flowers, fruit and vegetables growing throughout the season. Enjoy coffee and cakes in a restored Victorian vine house and shop for gifts and plants. 

Helmsley Brewing Co. 

This brewery combines the best ingredients with traditional techniques to produce a range grown-up craft beers. Visit the brewery to find out what we do, see us brew and enjoy the beers. From organised tours to informal banter at the bar, we are sure that a visit to our brewery will make your visit to Helmsley even more enjoyable. 


The routing will be as follows using the Route letters above:

The 5 day, 4 night holiday will be routed A B & C

The 4 day, 3 night holiday will be routed around 2 routes of your choice of A, B or C 

The 3 day, 2 night holiday will be routed around 1 route of your choice of A, B or C 



Important Information


The correct clothes are important to ensure comfort during each walk. We suggest avoid anything with seams and buttons in sensitive areas. Clothing should take moisture from the body to the outside. Sweatshirts, thin pullovers and breathable jackets are ideal companions during the cooler days. Take light, waterproof jackets and trousers in case there is rain. On hot days we suggest a cap or hat and sunglasses to protect from the sun.

What makes this tour special
  • North York Moors National Park
  • National Centre for Birds of Prey at Helmsley
  • Helmsley Arts Centre and Walled Gardens
  • Helmsley Brewery
  • Rievaulx Abbey

Please note, not all of these will be visited on the shorter tours. If you particularly want to see something on the list please inform us at the time of booking.

Pickup point
Helmsley, York YO62, UK View on Map