Cleveland Way Walking Holidays Baggage Transfer and Accommodation Booking

Let us do all the hard work - just choose where you want to stay. We'll make all the reservations, pick up your bags every morning and drop them at your destination the same afternoon

Cleveland Way Walking Holidays Baggage Transfer

Arrange all the accommodation yourself - just tell us where you'll be staying each night. We'll collect your bags every day and they'll be waiting for you when you arrive at your next stop

Cleveland Way Maps and Guide Books

To assist you in the planning of your walk and to accompany you along the way, we have selected the best maps and guidebooks you can comfortably carry in a rucksack pocket or walking jacket.

Cleveland Way

Cleveland Way Map for Walkers

Cleveland Way Walking Holidays

  • Distance of walk
  • Distance of walk
  • 110 miles
  • Walking Season Dates
  • Season
  • 23rd March - 19th October
  • Starting point
  • Starting point
  • Helmsley
  • End of walk
  • End of walk
  • Filey
Recommended for Extra Nights Recommended for Extra nights: Most towns are recommended on this route, particularly along the coast.
Cumbria Way Walking Holidays Trail Planner Download

Each trail planner contains details of travel, overnight stops, points of interest, suggested routes, relative distances and the services we can provide. Trail planners cost £5, but for each planner you download, we will take 5 off the cost of your booking on that trail

Cleveland Way Trail Planner

The Cleveland way was opened in May 1969 as one of the national trails of Britain (it was the second one established after the Pennine Way). It stretches for approx. 106 miles along the edge of the North York Moors and the North Yorkshire Coast, there are a couple of extra deviations that you could take which will put the distance up to about 110 miles. The scenery encompasses farming landscapes and forests, some unchanged for many years, dramatic rolling country with abrupt scarps and sandstone edges some with limestone capping, bleak moorlands, dramatic cliff and beach seaside scenery. All this is punctuated at intervals with interesting market and fishing towns steeped in history and literary association. The walk must not be underestimated there is a lot of ascent and descent, traverses over high moorland and some steep climbing.

Highlights of the Cleveland Way include, the remains of the Norman Rievalaulx Abbey, and Whitby Abbey, the Captain Cook Monument, and Robin Hoods Bay with it's cliff-hanging cottages. 


Typical Itinerary
Stage 1: Helmsley to Sutton Bank (10.2 miles).
After your arrival in Helmsley, if you have not overnighted here it is certainly worth a look round and additional information on the walk and the North York Moors National Park can be obtained from the Nat. Park HQ , The Old Vicarage, Bondgate, Helmsley (T: 0439 70657). Today is fairly easy so you could start at lunchtime from Helmsley's Market Square and include a look at Rievaulx Abbey which is about a half mile detour and you could also walk another detour to visit The White Horse of Kilburn, a limestone horse created by removing turf from down land. The "Big Peak" of the day is the climb up to Hambleton Hill, about 700 feet of ascent from Nettledale. There are several hamlets where you could stay for your first night at around ten miles at Sutton Bank, Cold Kirby, Hambleton or Kilburn. 

Stage 2: Sutton Bank to Osmotherley (12 miles).
Today is a walk at around and over 1000 feet along the Hambleton Hills from Sutton Bank / Kilburn, If you have stayed the night in Kilburn you will have a steep climb up to regain the height you lost. You travel today along the western edge of the national park itself on drove roads steeped in history. You will pass by many tumulus and over moorland, climbing up to Hambledon End at 1309 feet, the high point of the day. There are great views from the ridge , but little scope for refreshment until you drop down to Osmotherley with its quaint shops, cafes and three old pubs. So remember to take a packed lunch with you! Osmotherley itself is a fine old market town which grew as a green village at a road junction. There is a Youth hostel and altogether it is a fine place to stop.

Stage 3: Osmotherley To Clay Bank Top (11.5 miles).
The section today is said to be the most strenuous of the tour, a roller coaster of a walk up and down the Cleveland Hills, including the best walking within the park. You should have some excellent views once again to the agricultural plains to the north west and the moors to the south east. You should bring all your own rations today, as there are few stops en-route. Much of the accommodation is off route and you may want to ask if you can have a lift back to where you can regain the route. 

Stage 4: Clay Bank Top to Kildale/Great Ayton (9.2 miles).
A shortish day today, but you still have to climb up to the summit of Urra Moor and Round hill which at 1489 feet is the high point of this journey. The moors can be pretty windswept and bitter on occasion, but there are wide sandy paths worn into the hillsides between the grousey fields of heather to make good progress on. These can be boggy in places despite the sand and there have been some counter erosion remedies in place such as flagstones that can be hard on the feet at times. From Tidy Brown Hill you descend into the village of Kildale where you can find accommodation either there or a couple of miles away.

Stage 5: Kildale/Great Ayton to Saltburn (14.7 miles).
An interesting day's walk as you head down to the coast at Saltburn and the walk begins to take on a different character to the woody scarps and open moors that you have been used to up to now. Firstly the route climbs up Easby Moor to visit Captain Cook's memorial (he was born nearby), gives you the opportunity to detour by about a mile to climb the eroded sand stone stump of Roseberry Topping then skirts around the town of Guisborough and through the farming settlements of Slapewath and Skelton before meandering down with the Skelton Beck to the sandy seaside town of Saltburn -By- The -Sea, and the prospects of a good ice cream and fish and chips. It is quite a pretty place thoroughly re-organised by the Victorians, but you can still sense the old days of smuggling and crime rackets. If you are only doing half the walk, there are rail connections here to Middlesborough.

Stage 6: Saltburn-By-The-Sea to Staithes (8.8 miles).
Today is quite an easy walk along the coast to Staithes (Pronounced Stairs locally), there are nevertheless a couple of stiff climbs up to Hunt Cliff and to Micklow Hill and you will be climbing up around 1000 feet! Your second cliff at Boulby, is the highest on the East coast of England. In between the hills you drop down once again to sea level losing all the height you have gained but at least there is the chance of an ice cream stop. Walkers should beware of the cliff edges where the path largely runs: it maybe undercut in places and is prone in the long term to erosion, also beware of the cliff edge in strong winds. There is a lot of accommodation enroute today and some folk might prefer to walk on to Ravenscar to stay the night, but we do recommend that you spend a substantial amount of time (if not overnight) in the beautiful and largely untouched fishing village of Staithes, and discover the old coastal Yorkshire with its fleet of fishing Cobles (flat hulled, sharp prowed fishing boats, said to have come from viking design) in the harbour.

Stage 7: Staithes to Whitby Bay (11.5 miles).
A second fine day of coastal walking along the cliff tops over to Runswick Bay and then Sandsend, past more historical mineral workings, until you reach the long sandy Upgang beach which stretches over 3 miles to Whitby Sands and probably the most special town along the route: Whitby Bay. Once again this is a popular tourist destination and boasts having the best fish and chips in the British Isles and who is going to argue with them, they used to catch whales as well! The town has some fine buildings and there is a variety of accommodations including a Youth Hostel up by the Abbey, itself having been a scene from dracula.

Stage 8: Whitby Bay To Robin Hood's Bay (6.5 miles).
A shorter day is recommended here today because there is so much to see and enjoy in these two famous towns. They are both steeped in history, not just the fishing and the smuggling, but in Whitby you have a religious background and at R.H.B. you have a slightly obscure historical legend concerning a particular man who the town is named after! In between the towns there is walking over the brooding hill cliffs of Whitestone point, with some rock wave cut platforms, little beaches and even some small waterfalls approaching RHB. For the last part of the walk you may meet up with some coast to coast walkers, and can compare the two walks. The towns are very busy during the holiday season, but there is quite a bit of accommodation about. 

Stage 9: Robin Hood's Bay to Scarborough (15 miles).
To make up for the shortish last couple of days today is real hike into the major Yorkshire resort and fleshpot of Scarborough. You may feel a little different to others there walking along the promenade with your boots and rucksacks on! Like it or not all the fun -fair and ice cream kitsch is an important part of British holiday life and has been exported all over the World in various guises. The walking involves a coastal roller coaster of sea cliff path hills, staying very close to the edge for much of the time. Altogether there is about 1300 feet of total ascent over the 15 miles. There are limited refreshments enroute, and some interesting coastal feature names, such as Dab Dumps, Boggle Hole, Beast Cliff and Sailor's Grave. Today's is a brooding, lonely, lovely walk.

Stage 10: Scarborough To Filey (10 miles).
Final stage with only a total of 500 odd feet of ascent to go, a warming down walk if you will! Out of the bustle of Scarborough the way takes you out along the esplanade and the golf course to Cayton Bay. You should have time to visit the old castle and the Spa complex. The walk then hugs the cliff quite closely before reaching its official end at a style at milepost 103. Most people carry onto Filey and end at the North Cliff Country Park, Filey Brigg . . . . . Congratulations! 


General Information
Arriving and departing by train
Helmsley at the start of the route has no railway station, there is Malton 16 miles away which is the most convenient because it links with a reasonable bus service to Helmsley. There is also Thirsk Railway station 17 miles away and a limited bus service. At the end of the tour you can leave from either Filey Railway station or from Scarborough which has good connections via York. For details of timings and connections, please contact National Rail Enquiries on Tel: 08457 48 49 50 (24 hour service, local rate call) Or you can try to phone Malton Station directly on 01653 642155.
Arriving by Bus
Bus services run to Helmsley from Malton via Pickering, Middlesborough, Thirsk and York (Limited Days only). There are also services back from Filey to Scarborough. For timetables relevant for when you travel you can contact the East Yorkshire Travel Office Tel: Scarborough 01723 375463. United Autos, Tel: Darlington 01325 468771, York City Buses Tel: York 01904 624161. 
Arriving by car
Helmsley is close to York on the A170 and is well sign posted from York's Large ring road. At Helmsley there is a car park on the north side of the town at the start of the Cleveland Way and a weekly parking ticket is available from Helmsley Tourist Information Centre in the market place. You will be able to return to your car in Helmsley using the bus from Filey via Scarborough. If you are leaving the car for more than a week, then contact Helmsley Police Station on 01439 70310 if you cannot get through then please contact the larger Malton constabulary on 01653 692424. They will need your vehicle's particular details, so that they are aware of it. 
Most convenient international airport
A) Leeds - Bradford B ) Teeside - Newcastle, then rail connections to York and onwards. But if you are coming up from a London airport, an Intercity Train to York is pretty efficient and from there you can take a bus to Helmsley. 
From The Cleveland Way Project, North York Moors National Park, The Old Vicarage, Helmsley, Yorkshire, YO6 5BP, You can obtain the free booklets useful for the walk 
1) Moors Connections: Provides up to date timetables for all bus and rail services operating in The North York Moors National Park and marks stops suitable for joining the Cleveland Way.
2) Cleveland Way Accommodation and Information Guide. If you are searching for your own accommodation instead of using this booking service , then this booklet lists accommodation, banks, shops and refreshment stops along the route.

For the latest UK train information call 08457 48 49 50, or visit www.nationalrail.co.uk
For UK local bus timetable and information visit www.ukbus.co.uk