Helmsley Short Break: Laidback Exploring in the North York Moors

For a few days walking in the North York Moors National Park, you couldn’t ask for a better base than Helmsley. This winsome market town has a bit of everything: a medieval castle, a pretty walled garden, an arts centre, tempting delis, good pubs, even its own brewery. It’s also ideally placed for healing out on foot. Both the Cleveland Way and Ebor Way begin here, and there are plenty of other paths wriggling into the surrounding hills.

This laidback short break offers three super circular walks from Helmsley itself – no transfers required – which take in peaceful dales, magical woodlands and the mighty ruins of Rievaulx Abbey. There are also options to visit nearby attractions such as Helmsley Castle and the National Centre for Birds of Prey, where you can get up-close to the resident raptors. Every night, you’ll return to a comfy inn and a warm North Yorkshire welcome.

Tour Overview

The icons below highlight the distance, difficulty and theme of this itinerary.




Walks from 10.5km to 13km




High Hills & Moorland / Rolling Countryside


History / Food & Drink

Activities & Experiences

Walking / Heritage

Helmsley Short Break: Laidback Exploring in the North York Moors

Here’s everything you need to help you plan your very own walking and exploring break in the North York Moors National Park. Click on the blue arrow tabs below for more information. To save this itinerary to view later, use the Save to My Rucksack button at the top of the page.

Tour details

This itinerary is being operated by Compass Holidays, who specialise in walking, cycling and activity short breaks and holidays in a variety of UK, European and worldwide destinations.

With more than 30 years’ experience, Compass Holidays allow you to get under the skin of the history, culture and natural beauty of some of the world’s most iconic and spectacular locations.

Compass will arrange your whole tour: you just need to arrange transport to your first location.

  • Accommodation at the stated category with breakfast.
  • Luggage transfers.
  • Full tour pack with colour-coded routes on local maps.
  • Smartphone app with GPS routes.
  • 24-hour emergency helpline.

NOT INCLUDED: Lunch, dinner and drinks; entrance to attractions; buses and/or ferries unless otherwise stated; tourist taxes where applicable.


Spend a few days walking around Helmsley, the only market town in the North York Moors National Park. This flexible itinerary allows you to stride out into the surrounding countryside right from the door of your comfy accommodation, on a succession of circular routes; choose to stay for two, three or four nights – the itinerary below is a suggestion.

The handsome town of Helmsley, the start-point of the Cleveland Way, is the ideal base for exploring the wider area. Not only is there great walking on the doorstep, there’s a host of other things to do, from meeting the raptors at the National Centre for Birds of Prey to visiting the 900-year-old castle, taking tea in the Walled Gardens and sampling the wares of the town’s craft brewery.

Overnight in Helmsley.

Today, follow the Cleveland Way from Helmsley’s fine old market square, past the castle ruins, to head up into the hills. The route to Rievaulx Abbey is a delight, climbing gently before dropping down through bluebell woods to reach the peaceful village and ruins of 12th-century Rievaulx, the first Cistercian abbey in the North of England. From here, return to Helmsley the same way, enjoying the sweeping views from a different angle.

Walk: 11km. Overnight in Helmsley.

Today, head north from Helmsley through the woodland belt of Beck Dale, following an idyllic babbling brook. Stroll across lush-green fields, breathing in the fresh country air, and return via another magical woodland, Ash Dale. You’ll be back in Helmsley in good time to explore some of its other attractions.

Walk: 10.5km. Overnight in Helmsley.

Another lovely loop from Helmsley heads out across sheep pastures and wide-open fields flecked with wildflowers to enter the woodland ravine of Riccal Dale, where the River Riccal gurgles away.


Walk: 13km. Overnight in Helmsley. Depart after breakfast the following morning.


This itinerary uses three-star B&Bs, hotels or inns in Helmsley.

Food & Drink

The North York Moors has eating options for all tastes and budgets, from Michelin-starred restaurants to pretty cafes. Helmsley has plenty of eating and drinking options, including its very own brewery, where Striding the Riding – the official beer of the Cleveland Way – is produced.


The grade of this tour is moderate. Walks involve some climbs and the ground may be muddy in places.


  • Circular route from Helmsley, via Rievaulx Abbey, 11km
  • Circular route from Helmsley, via Beck Dale 10.5km
  • Circular route from Helmsley, via Riccal Dale, 13km


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

  • Rievaulx Abbey – Discover the impressive ruins of one of England’s most powerful Cistercian monasteries and visit the museum, where previously unseen artefacts tell the story of the abbey’s rise and dramatic fall.
  • Helmsley Castle – Unlock 900 years of history: discover how the castle evolved over the centuries, from a mighty medieval fortress to a luxurious Tudor mansion, to a Civil War stronghold to a romantic Victorian ruin.
  • Helmsley Walled Garden – This historic five-acre garden has vibrant displays of flowers, fruit and vegetables growing throughout the seasons. Coffee and cakes are served in a restored Victorian vine house.
  • Helmsley Brewing Company – This brewery combines the best ingredients with traditional techniques to produce a range of craft beers. Take a tour and taste beers in the tap room.
  • National Centre for Birds of Prey, Helmsley – Visit raptor aviaries, watch flying displays or book hands-on bird experiences.


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

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.


The grade of this tour is moderate, with walks of between 10.5km and 13km per day. This tour is available from April until September.

The correct clothes are important to ensure comfort during each walk. We suggest avoiding 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 on 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.

We advise that you check opening times and booking restrictions before travelling.

Please check out these links for latest advice when in the countryside:

Countryside Code

COVID-19 Guidance

Interactive Map

Please see the interactive map for more details.

Maps, Guidebooks & Merchandise

The official guidebook and map for the Trail are available from the National Trails Shop along with a wide range of gifts and other merchandise.