North Yorkshire

Cleveland Way – 9 Nights

Apr, May, June, July, Aug, Sept, Oct£1389 pp

Beat the Price Rise! Book by Sunday 30th June!£1349 pp

Book your adventure
Speak to an Expert

Or call us on

017683 71289


Dates may vary in price due to demand throughout the season and are subject to changes from time to time. We recommend booking your trip well in advance to secure the best pricing available for your preferred dates.

If you don't see a date suitable, please call on +44 (0)17683 71289 to organise a custom date.


Choose a different date

HOW MANY PEOPLE There are no more spaces available for this date


Cleveland Way – 9 Nights

No. of People: 1



TOTAL £999

Back to search
About this Adventure

A classic walking route, the Cleveland Way was the second recognised National Trail in England & Wales. In a beautiful and ever-changing landscape, you cross the rugged heather moorland of the North York Moors National Park until reaching the coast at Saltburn-by-the-Sea. From here, the trail runs south along the North Yorkshire coastline, taking in the renowned villages of Robin Hood’s Bay, Whitby and finishing in Filey.

A great mix of scenery and terrain awaits hikers on this trail, from moorland to coastal paths; this trail has it all!

Quick Facts

  • 9 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
  • Approx. 110 miles (177km) and 18250ft (5562m) of ascent
  • A spectacular blend of hills, coast and history

About & Details

The Cleveland Way was established in 1969 and was the second official National Trail of England (the first being Pennine Way).  The trail starts in the beautiful market town of Helmsley and follows a well-trodden trail through the heather-clad moorlands of the North York Moors National Park until you reach the coast.  From here, the trail runs down the dramatic North Yorkshire Coastline to Filey, taking in iconic villages such as Robin Hood’s Bay and Whitby (famously the home of Whitby Abbey, inspiration for Bram Stoker’s gothic tale ‘Dracula’).

The scenery experienced along the trail is split into two halves.  From Helmsley to Saltburn-by-the-Sea, you will explore the inland geography of North Yorkshire, surrounded by the dramatic moorland landscapes and wild vistas, then spending your evenings in quaint villages tucked away in the valleys. From Saltburn-by-the-Sea to Filey, the scenery shifts, and we begin to experience the rugged Jurassic coastline of North Yorkshire. You’ll walk along the cliffs, looking down to the sea and discovering secluded coves and bays. The atmosphere becomes more vibrant, with vivid seaside towns and perhaps an evening drink watching the sunset.

If you love it so much you’re wanting more, you can extend the route and make it a round trip back to Helmsley via the Tabular Hills Walk (please discuss with us when booking). Alternatively, you could embark on the Yorkshire Wolds Way between Hessle and Filey.

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 waterproof jacket and trousers, a small day sack and comfortable walking boots but you will receive a more detailed kit list upon booking. This trip is based on 2 people sharing, so if you are a solo traveller please contact us for further details and we will be happy to help.


  • 9 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 £90 per person per night (subject to availability)
  • Solo traveller supplement £90 per person per night
  • Odd group supplement £90 per group per night may apply if a single room is required
  • Extra night prior to start (single room) £180 per person
  • Extra night prior to the start (twin room, needs 2 people) £95 per person
  • Extra night at the end of the event (single room) £180 per person
  • Extra night at the end of the event (twin room, needs 2 people) £95 per person

Please select from Optional Extras at checkout.

Getting there and back

Getting There

By Road: Helmsley can be accessed by car via the A1(M). A19 and A170 – from either the North or the South.

By Public Transport: Train and Bus services are available from York, Northallerton or Newcastle. Check traveline.info for the latest public transport information.

By Air: The nearest airports are Leeds Bradford International Airport or Newcastle International Airport.

Getting Away

By Road: Filey can be accessed by car via the A64 / A170, then across onto the A1(M) to head North or South.

By Public Transport: There are frequent train services running from Filey to Sheffield which take approximately 2.5 hours, or up to Scarborough (15mins) from where you can go back to York.

By Air: The nearest airports are Leeds Bradford International Airport or Newcastle International Airport

Evening meals and lunches

You can purchase evening meals either at the accommodation or nearby. When our event planners send you the schedule with itinerary you could prearrange directly with the accommodation or during the walk.

For lunches we would suggest bringing some of your own favourite snack bars and then asking the accommodation for a packed lunch for the following day and also supplementing that at stops en-route.


Accommodation is generally at B&B, guest houses and small hotels. Once booked in, your event planner will send you a list of your booked accommodation. It is possible to adjust according to preference at this stage so please mention it if you wish to change.


If you would like to bring your four legged friend, then we will do our best to source dog friendly accommodation. It is usually possible but if it were not, then we would suggest a change of date to enable it or offer a refund. There may be a small surcharge for the overnight stays. Therefore, once booked in, please alert your event planner that you would like to bring your dog and we can proceed from there.

Need a guide?

If you would prefer to have a guide for your walk, even just for one day, then we are happy to help. We can provide a qualified leader (also first aid qualified) to lead your trek or on just one of the sections. Just ask us.
A guide can not only take the stress out of navigation, but you will also find them a great asset in terms of providing an insight into all things environment and nature.

Dates and prices

For available dates please see the ‘build your trip’ option on the left hand side on desktops or at the bottom on mobiles. You can reserve your space via this route.

After you book

After placing your booking with us, you will in the first instance receive an automated email from our system confirming receipt of your reservation. If you don’t receive it, it is worth checking your spam/clutter folder.

In the process of placing your booking, you will generally set up an access password to our online gateway where you can review the details of the booking.

Your personal event planner will then be in touch with you to start to confirm the details. This contact will usually be taken up in the working day after receipt of your booking, but may, in busy times, take a little longer. The event planner will then liaise with you regarding the details of the course. If you have any specific requirements, please do mention it at this stage.

At the end of your trip

Unfortunately, all good things come to an end at some point and when you arrive at the end of the trail, you have one of several options. If you have not booked an additional night’s stay then we can transfer your luggage to a location of your choice. From there you may have onward travel arranged as per the ‘Getting There and Back’ tab above.

Some people like to treat themselves to a night’s stay at the end. And why not? You’ve earned it. You can arrange this as an optional add on with your event planner.

Book your adventure


  • Day 1 - Arrive in Helmsley

    Arrive at your accommodation in Helmsley.

  • Day 2 - Helmsley to Boltby

    Your first day starts with a comfortable climb out of the Rye Valley to Rievaulx, where a short detour can be made to see the imposing remains of Rievaulx Abbey.  From here, the route climbs further to Sutton Bank, where a second short detour can be made to see the White Horse of Kilburn (included in today’s mileage) – an impressive hill figure cut into the hillside by locals in 1857. Your route then tracks back along to Sutton Bank and through woodland where you leave the trail at Little Moor and head down into the village of Boltby.

    Approx. distance 14 miles (23km) and 550m (1800ft) of ascent.

  • Day 3 - Boltby to Osmotherley

    From Boltby, return to the trail at Sneck Yate Bank. Today, you walk along the historic Hambleton Drove Road, an ancient route used by Scottish cattlemen to move their livestock down to market towns in England. The scenery begins to take a wild turn, with the road giving a great outlook of the hills and moorland around you. Your day ends in the village of Osmotherley; be sure to re-stock supplies here as future opportunities can be sparse.

    Approx. distance 10 miles (16km) and 400m (1500ft) of ascent.

  • Day 4 - Osmotherley to Great Broughton

    Rejoin the trail and prepare yourself for a remote and undulating day – it is both very scenic and very enjoyable, however the exposure in poor weather could make it challenging. You will experience the heart of the moors, with your efforts being rewarded with the panoramas that highlight the vastness of the hills around you. Your day ends at Clay Bank, where you will be transferred to your evening’s accommodation.

    Approx. distance 11 miles (18km) and 820m (2700ft) of ascent.

  • Day 5 – Great Broughton to Great Ayton

    The remote nature of the landscape stays with you today, as you head through the highest point of the North York Moors on Round Hill (454m).  This section is exceptionally impressive in summer when the heather is blooming and the weather favourable. There is no easy access to facilities today, so make sure you’re well equipped for your day in the moorland wilderness!  Your day ends with an ascent onto Easby Moor, where you will find Captain Cook’s Monument overlooking Marton, the suburb of Middlesbrough where Captain Cook was born in 1728.  From here, it’s a simple walk down into the village of Great Ayton where you will find your accommodation for the evening.

    Approx. distance 13miles (21km) and 425m  (1400ft) of ascent.

  • Day 6 –Great Ayton to Saltburn-by-the-Sea

    Your day starts with an ascent onto Great Ayton Moor, where you decide whether to summit the striking Roseberry Topping (mileage includes the diversion) or to continue on your day’s hike. You then stroll through Guisborough Woods, where you can opt to divert from the trail to see Gisborough Priory if you have time. You spend your final inland miles hiking through quiet countryside until you reach Skelton, where the scene starts to become much more populated.  After the sparseness of the moors, you will be glad of the opportunity to restock your supplies and rest overnight in Saltburn-by-the-Sea.

    Approx. distance 15miles (24km) and 790m (2600ft) of ascent.

  • Day 7 – Saltburn-by-the-Sea to Runswick Bay

    You rejoin the trail for your first full day following the coastline! Your route takes you over Hunt Cliff and through to Skinningrove, from here you will traverse Boulby Cliff (the highest cliff on the east coast of England) and then take in the vibrant harbour village of Staithes, which is a great spot for a rest overlooking the North Sea. From here you continue along the cliffs to the lovely little village of Runswick Bay, where you will stay for the evening.

    Approx. distance 12miles (20km) and 550m (1800ft) of ascent.

  • Day 8 – Runswick Bay to Robin Hood’s Bay

    After a steep push uphill out of Runswick Bay, a short but undulating day of hiking awaits you, allowing you to take in fine clifftop views and spot coastal wildlife. From Sandsend, the hiking is relatively easy through to Whitby, so you should arrive in plenty of time to be able to explore this bustling harbour town – steeped in the history of Captain Cook & St Hilda, and in the legend of Dracula. You end your day by following a well-trodden route from Whitby down to Robin Hood’s Bay, a charming village with an interesting smuggling history.

    Approx. distance 15 miles (24km) and 610m (2000ft) of ascent.

  • Day 9 – Robin Hood’s Bay to Scarborough

    Continue on your hike along the clifftops to Ravenscar – enjoy the views back along yesterday’s route. For today, it’s mostly short, sharp undulations on the trail, until you reach the outskirts of Scarborough, where the trail becomes much flatter as you arrive in the seaside resort town.  Points of interest today include Hayburn Wyke, an attractive boulder beach where a small waterfall tumbles into the pebbles, and the remains of Scarborough Castle.

    Approx. distance 15 miles (24km) and 640m (2100ft) of ascent.

  • Day 10 – Scarborough to Filey

    Leaving the hustle and bustle of the seaside town of Scarborough, you will soon see the former location of the Holbeck Hall Hotel which slipped into the sea in 1993. Your route then follows the coastline and headlands; take time to savour the coastal scenery on your final walking day! As you reach Filey Brigg, your hike is nearly complete, and you will join The Yorkshire Wolds Way into Filey – time to celebrate the completion of the Cleveland Way trail!

    Approx. distance 11 miles (18km) and 350m (1150ft) of ascent.


Please note: This itinerary is a guide only. Timings and mileages are approximate.

We will always endeavour to accommodate you in the locations detailed in the above itinerary. Due to very high demand, some accommodation providers may occasionally have limited availability and so we may need to accommodate you in an alternative location, nearby. In this case, we will arrange a taxi transfer for you to take you from the trail to your accommodation and back again the following morning. An additional charge may be payable. We will notify you of this when confirming your booking

The Route

Find some of the reviews our wonderful customers have left for us below, or read them all here!

Heather Parr
3 months ago

Maximum Adventure exceeded expectations, planning a trip for me last minute and off season through the glorious Lake District. The hotels were top rate, as was the food and my daily gluten free sandwich. Nathalie got the route guide sent to me in a couple of days and the baggage service was impeccable. It was the only tour guide company that responded immediately to my last minute request. Looking forward to more adventures with your company!!!

Chris Evans
3 months ago

David and I walked the Speyside Way in September 2023 and very much enjoyed the adventure. Maximum Adventure Ltd organised our nightly accommodation and uplifting of our luggage in a seamless manner, which made the whole trip so easy with no stress. This is the second time that I have personally used Maximum Adventures Ltd and I would recommend them to others as they offer a friendly and efficient service.

Göte Fredriksson
4 months ago

We realy appreciated the tour we did on Hadrians Wall path in May.Beautiful scenery, decent weather, god arrangements including lodging, transport, bagagehandling etc. We came well prepared . In this preparation Maximum adventures gave us great support, as we are coming from abroad with no knowledge of conditions on the path. We had great BnBs and could concentrate on de daily walks that gave us great pleasure.Thank you England and Hadrians Wall path for your friendly reception and well mantained walking path.Thank you Maximum Adventures for your good service.We would love to come back in the future.

Jerry Kashinski
4 months ago

Maximum Adventure did a great job for us. With less than a month's notice, it set up an itinerary, lodging and luggage porterage for a walk from Carlisle to Newcastle, England along Hadrian's Wall. The lodging was fantastic, as was the itinerary and support during the walk. We'd definitely use Maximum Adventure again and would recommend them without reservation!

Fiona Reilly
5 months ago

I was part of a climb on 23/09, didn't think I would make ut, but I did. The descent was a different story.. I got jelly legs and lost my confidence. If it wasn't for James, my Sherpa would never have made it. Can't thank him enough, Will, met you briefly.Both of them were very knowledgeable, we had the most amazing views at the summit...the pain is still worth it and

Tom Graham
5 months ago

I walked the West Highland Way with my dad and brother. The organisation was excellent by Samantha. Itinerary and instructions were clear and all the bookings and luggage transfers went smoothly. As a result we were able to ensure the fantastic walk and not worry about anything. I would happily recommend Maximum Adventure to others.

Sarah Bracken
5 months ago

Absolutely brilliant guide - knowledgeable, interesting and humorous in addition to looking after our safety so well - making sure we ate and suggesting when to layer up! Would highly recommend!

Diana Straub
6 months ago

We just got home from our 8-days Hadrian's Wall hike and we just loved it!Everything was perfectly organized!We had great B&Bs and hotels with very friendly, welcoming and helpful staff. Our favorite was the Dacre House with Clare. But then again, all were great!The luggage was always at the day's destination, no matter how early we got to the accommodation.The description of how to get to the accommodations were clear and precise.The road map and the guide book were waiting for us as we got to the first B&B and were very helpful and interestingThanks, Maximum Adventure!

Kristin Hentschel
6 months ago

Praise for the West Highland Hike and the Maximum Adventure planners, esp. our planner Samantha. Great experience in every regard.

Simon Bradish
6 months ago

Booked for the 3 UK Peaks adventure, it was organised perfectly and everything when to plan. Accommodation was good, transport excellent, our guide (Patrick) brilliant, so cannot fault the trip and adventure. I personally expected too much from myself and was unable to fully summit as this adventure is not for beginners, I climbed Kilimanjaro in 2003 when I was 42 and twenty years later, although relatively fit, my endurance didn't last. So I did a half summit for Ben Nevis & Scafell, thanks to Patrick for letting go back down on my own, it was brilliant. With Snowdon, a half summit is tricky as you can't descend the way you go up, so I decided to do some hiking in the area while the rest of the group did the climb. I took a chance and went to the ticket office and managed to get a single return ticket up to the summit of Snowdon at 9am which returned down by 11.30am. I was hoping to see my group on top and spring a surprise but the weather was terrible. I highly recommend the trip but make sure you are fit enough otherwise as there is an emphasis on time, so a slow walk up is going to slow everyone down and really delay the trip. Have Fun, Simon Bradish

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

You may also like...