Cleveland Way Run

Cleveland Way Run

A trail running holiday through the North York Moors and along the Cleveland Heritage Coast, from Helmsley to Filey.

3 to 8 nights
42-111 miles
Easy / Moderate to Strenuous

From £400 per person

Find your holiday

About the trail

High open moorland and breezy coastal running await on the Cleveland Way, a trail running holiday of two distinct halves. From Helmsley, delve through the North York Moors National Park. Here the route hikes to its highest point at Roseberry Topping, but it’s suitably apologetic with smooth, pleasant trails and great views over purple moorland. Soon you’ll take on the North Yorkshire and Cleveland Heritage Coast, where you’ll spy sandy beaches from hilly cliff-top trails. Top up your reserves with a seaside fish and chips and press on to the route’s end in Filey. It’s a scenic, refreshing run with some challenging gradients.

Choose your route

  • This route includes dog friendly tour options Cleveland Way Run
  • This route includes dog friendly tour options Cleveland Way Short Running Break

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

Walking tours available

We also organise walking holidays along this route. Find out more.

About this route

4 to 8 nights
111 miles
Easy / Moderate to Strenuous
2nd January to 24th December
Includes Dog-Friendly Tours

From £580 per person

Cleveland Way Run

Mixing high, open moorland with the breezy joys of coastal running, the Cleveland Way is a journey of two halves.

First, inviting trails guide you around the North York Moors National Park, visiting woodland, green dales, and moorland that turns deep purple in late summer. The route lifts you to its highest point, with huge views to match, at Roseberry Topping.

The second half rewards with classic coastal terrain: the full expanse of the North Yorkshire and Cleveland Heritage Coast. An undulating route carries you across cliff tops, around wide, sandy bays and clandestine coves, and through the narrow streets of small resorts.

With far-reaching views, castles, ancient stone crosses, fishing villages and much more, the Cleveland Way is a rewarding journey from moor to coast.

Available tours

Code Tour Duration Difficulty Price per person
R-CLEVW1 From Helmsley to Filey 4 nights, 3 days running Strenuous £580
R-CLEVW2 From Helmsley to Filey 5 nights, 4 days running Demanding £670
R-CLEVW3 From Helmsley to Filey 7 nights, 6 days running Moderate £900
R-CLEVW4 From Helmsley to Filey 8 nights, 7 days running Easy / Moderate £1005

Cleveland Way Trail Run 4 nights, 3 days running

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather
  • Holiday Highlights

Important information

This tour is available to book all year, however out of season from the end of October to March, there may be a supplement for luggage moves, which will be moved by taxi rather than the usual luggage courier.


Travel to Helmsley where your first night's accommodation will be booked

Day 1

Helmsley to Clay Bank Top(T). 34 miles (54km) / 4941 ft (1506 m) ascent

Day 2

Clay Bank Top(T) to Runswick Bay(L). 36 miles (58km) / 4715 ft (1437 m) ascent

Day 3

Runswick Bay(L) to Filey. 41 miles (65.5km) / 4905 ft (1495 m) ascent


Depart from Filey after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£70.00 per person / per night
Single Supplement
£55.00 per person / per night

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
© Contours Walking Holidays Cleveland Way Run map
111 miles (178 km)
2nd January to 24th December

Holiday highlights

Visiting locations rich in history and heritage, from Rievaulx Abbey, Scarborough Castle and Mount Grace Priory to the inspiration for Dracula in Whitby.

Spotting the variety of wildlife, from grouse in the heather moors to the sea birds along the coastline.

Being rewarded by dramatic coastal views as you reach the North Yorkshire coastline on the approach to Filey.

What's included?

  • 4 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

If you would like to add an extra night into your holiday to explore the locations along the Cleveland Way, or to take a break from running for a day, then there are plenty of interesting locations to choose from along the trail.

Runswick Bay is a pretty village by the seaside that makes for a perfect relaxation stop, with its red-roofed cottages, golden beaches and tiny Methodist chapel built in the early 1800s. Just a few miles down the road from here is the fishing village of Staithes, famed for its community of well-known artists and their highly popular Arts Festival during the autumn. Here, you can visit the art galleries and learn more about the village?s history, before enjoying lunch or afternoon tea in one of their many pleasant cafes.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night

Tour Facts

Total distance: 111 miles (177.5 km)
Duration: 4 nights, 3 days running
Minimum daily distance: 34 miles (54 km)
Maximum daily distance: 41 miles (65.5 km)
Code: R-CLEVW1 Grade: Strenuous
Season: 2nd January - 24th December
Start of holiday: Helmsley
End of holiday: Filey

Route Profile

Cleveland Way Trail Run Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are Leeds-Bradford, Manchester and Teesside International Airports.

By Rail - The nearest rail stations to Helmsley are either Malton (about 16.5 miles away) or York (about 25 miles away). There is a rail station at the end of the trail (Filey).

By Bus - There are no direct bus journeys from Malton to Helmsley, so a taxi would be required. There is a rather infrequent bus service from York to Helmsley, Monday to Saturday only, but a taxi would be a much quicker option, and essential on Sundays/in between buses. Various bus services run from Filey.

From London - Trains run from London Kings Cross station to Malton and York. A bus/taxi will be required to Helmsley.

Return To The Start - The easiest way to return to the start of the trail is to take a train from Filey to Malton. From there, a taxi will be required to Helmsley.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.
"Along the Trail" by Sam Cockerham (2021) "Along the Trail" by Sam Cockerham (2021)
"At the finish line" by Sam Cockerham (2021) "At the finish line" by Sam Cockerham (2021)