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North of England

The Cleveland Way

April, May, June, July, Aug, Sept, Oct £999 pp

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The Cleveland Way National Trail is a 110 miles (177 km) walking route through beautiful and ever-changing landscapes and scenery. Officially opened on 24th May 1969, it was the second recognised National Trail in England and Wales.



Quick Facts

  • 10 nights’ accommodation
  • 9 days’ walking
  • Luggage transfers each walking day
  • Map and guide book plus detailed directions to your accommodation from the trail
  • Expert local knowledge and 24 hour emergency assistance during your trip
  • 110 miles (177 km)

About & Details

The trail begins from the market town of Helmsley then heads across the breathtaking heather moorland of the North York Moors National Park, before reaching the coast at Saltburn-by-the-Sea. From here you will follow the North Yorkshire coastline to Filey, passing old fishing villages and coastal towns.

The route will take you through Robin Hood’s Bay, the famous smuggler’s village, also the seaside resorts of Scarborough and Whitby – home to Whitby Abbey, the inspiration for Bram Stoker’s Dracula.

The Cleveland Hills and some of the coastal sections can be quite challenging but anyone with a reasonable level of fitness will find it manageable.

We take the stress out of your trip with expert local knowledge, hand-picked accommodation, luggage transfers and detailed support to help you find your way. You will need full walking kit including a waterproof jacket and trousers, a comfortable day sack and comfortable walking boots. You will receive a more detailed kit list upon booking. This trip is based on 2 people sharing, if you are a solo traveler please contact us for further details and we will be happy to help.


  • 10 nights’ accommodation in a good quality B&B or hotel with ensuite or private bathroom and breakfast
  • Luggage transfers each walking day
  • Map and guide book plus detailed directions to your accommodation from the trail
  • Expert local knowledge and 24 hour emergency assistance during your trip
  • Professional event organisation
  • Travel to the start and finish points of the trip
  • Lunches and evening meals
  • Personal insurance (for cancellation, accident, health, emergency evacuation and loss, theft of or damage to baggage and personal effects)
  • Guiding (please contact us if you would like this trip to be guided)

Optional Extras

  • Single room supplement £55 per person per night (subject to availability)
  • Solo traveller supplement £45 per person per night
  • Odd group supplement £35 per group per night
  • Extra night prior to start (single room) £95 per person
  • Extra night prior to the start (twin room, needs 2 people) £75 per person
  • Extra night at the end of the event (single room) £95 per person
  • Extra night at the end of the event (twin room, needs 2 people) £75 per person

Please select from Optional Extras at checkout.

Getting There and Back

Getting There

By road:

By public transport:

By air:

Getting Away

By road:

By public transport:

By air:


  • Day 1 - arrival in Helmsley

    Arrive at your accommodation in Helmsley.

  • Day 2

    Helmsley to Sutton Bank – 10.5 miles (17 Km)

    Your first walking day is a good introduction to the Cleveland Way. The walking is not too strenuous as it climbs out of the Rye Valley to reach the Hambleton Hills escarpment at Sutton Bank

  • Day 3

    Sutton Bank to Osmotherley – 11.75 miles (19 Km)

    Today you make your way along the limestone Hambleton Hills of the North York Moors National Park. You will be following in part an ancient route followed by drovers and travellers for centuries.

  • Day 4

    Osmotherley to Clay Bank – 11 miles (17.5 Km)

    This length of the Cleveland Way takes in the magnificent Cleveland Hills. The northern escarpment of the North York Moors National Park offers outstanding views both north across to Teesside and south and east into the moors and dales of the Park.

  • Day 5

    Clay Bank to Kildale – 9.5 miles (15 Km)

    This section continues the upland moorland theme – with a chance to visit the highest point on the North York Moors. Signs of old industry are never far away as part of the route joins the old railway line near Blowarth Crossing.


  • Day 6

    Kildale to Saltburn – 15 miles (24 Km)

    Today you enter Captain Cook Country and will come across several reminders of the famous explorer who grew up in Great Ayton. Heading north out of Kildale you will cross the Esk Valley rail line. This is one of the few surviving “country” lines.

  • Day 7

    Saltburn to Sandsend – 17 miles (27.5 Km)

    Today walk is a great introduction to the North Yorkshire coastline. You will soon understand why most of it falls within the designations of both National Park and Heritage Coast.

  • Day 8

    Sandsend to Robin Hood’s Bay – 10.25 miles (16.5 Km)

    leaving Sandsend you will be rewarded with some outstanding coastal scenery as well as visiting popular seaside resorts such as Whitby and Robin Hood’s Bay.

  • Day 9

    Robin Hoods Bay to Scarborough – 13.75 miles (22Km)

    This classic stretch of the trail heads up towards the distinctive heights of Ravenscar, so affording outstanding views across the landscape and sea.  You will encounter the hidden delights of Hayburn Wyke and its beach before the historic seaside town of Scarborough comes into view.

  • Day 10

    Scarborough to Filey – 11 miles (18 Km)

    This final length has some stunning cliff and coastal scenery to appreciate as you saunter through to the lovely old Victorian resort of Filey.


Please note: This itinerary is a guide only. It can be subject to change dependent upon viability, course members’ fitness, weather conditions, accommodation availability, or for any other reason that may be deemed necessary. Any timings are approximate and for guidance purpose only.

Why book with us

We know you have a choice of companies providing trips for your next adventures. Here are some of the reasons you should choose to travel with Maximum Adventure:

  • We are an established adventure travel business
  • We have been trading since 2002
  • We are financially protected in accordance with the 1992 travel regulation
  • Knowledgeable and available office staff
  • Qualified leaders and guides with ascents ranging from Ben Nevis to Mount Everest
  • All activities are risk assessed
  • We will provide you with the best service available
  • We are aware this is your holiday/your challenge and will do our best to make it an enjoyable and rewarding experience
  • We have many repeat clients stretching back over a number of years
20+ years adventure organisation experience
Full liability & financial protection
Leading provider of high quality adventure challenges
Great team of staff to support you

Payment Terms

  • Deposit £299 - at point of booking

  • Balance due 10-weeks before departure