9 Days & 8 Nights

4.7

Cleveland Way: North York Moors & Coast | 9 Days

Walking through the untouched landscapes of Northern England.
Helmsley Castle and the remains of the Norman Rievaulx Abbey.
Clifftop walking along the east coast, with sea views.
Crossing open heather moorland skirting the North York Moors.
Whitby Abbey, the Captain Cook Monument and Robin Hoods Bay.

The Cleveland Way explores an untouched area of Northern England where dinosaurs once used to roam. On this trail of varying landscapes, from high cliff tops to peaceful moorland, you will continually skirt the North York Moors National Park. Here pilgrims found peace and settled on these moors creating important abbeys and churches, the remains of which can still be seen today. Wander through historic villages, explore picturesque old shops, and enjoy local hospitality. Revel in the impressive views over the Cleveland Hills and also pass Rock Cliff, the highest point in Eastern England. This journey also hugs the coastline and takes you through such charming seaside towns as Saltburn-on-Sea and Filey. Read Ben Lerwill's celebration of the Cleveland Way featured in The Sunday Times.

From £995.00

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Itinerary

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Day 1 Arrive Helmsley and overnight

Arrive in Helmsley and take time to wander around the historic village with its picturesque old shops clustered around the market square.

Overnight Helmsley

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

The Feathers Hotel | Hotel

The Feathers is a local landmark standing on the bustling market square in Helmsley. The Feathers offers a blend of historic charm and traditional Yorkshire hospitality. You can enjoy informal dining in the Feversham bar or a quiet drink by the fire in the Pickwick bar. Wherever possible they aim to use locally sourced, fresh ingredients.

The Black Swan | Inn

The site of The Black Swan dates back to the 15th century, the house itself comprising of a Tudor house, a Georgian house, and an Elizabethan house.

This accommodation offers a warm welcome with cosy rooms, an in-house bar and restaurant, and easy access to Rievaulx Abbey, Helmsley Castle and Helmsley Walled Garden.

Orchard Cottage | Bed and breakfast

This charming stone cottage is situated in the middle of picturesque Helmsley, close to the North York moors and nestling by the Hambleton and Howardian Hills.

Day 2 Helmsley to Osmotherley 20 miles / 31.5 km

The first highlight of today's walk, Rievaulx Abbey ruins are worth the half-a-mile detour off the path, set in the wooded valley of the river Rye. As you approach Sutton Bank the Kilburn White Horse - a limestone horse created by removing down turf can be seen. The views from Sutton bank are wonderful, with a few climbs as you follow the old Drovers road to Black Hambelton. The day ends in Osmotherley; a quaint village with old pubs, shops and cafes.

Ascent: 545m / Descent: 440m

Overnight Osmotherley

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

The Golden Lion | Country Inn

An 18th Century stone inn overlooking the market cross of Osmotherley. The bedrooms are fresh and modern with oak doors and skirting as well as handmade oak wardrobes.

Queen Catherine Hotel | Bed and breakfast

The Queen Catherine Hotel is a family-owned pub offering food and accommodation in the heart of the North Yorkshire Moors. The hotel has a small selection of comfortable and well-appointed bedrooms, all of which have just been highly refurbished.

Three Tuns | Inn

Family owned, with an increasing reputation for high quality, freshly prepared food. The atmosphere at the Three Tuns is always warm, friendly and relaxed and the Rennie Mackintosh inspired interior décor is a delight. The residents lounge is designed to make you feel as though it’s your own home.

Day 3 Osmotherley to Clay Bank Top 11.5 miles / 18 km

This is the most strenuous part of the walk, like a giant rollercoaster walking up and down the Cleveland Hills. After a fairly easy start, prepare for switchbacks and a succession of ascents and descents toward Clay Bank. The views are stunning across the heather-clad moorland and the deep valleys to the south.

Arriving at the Clay Bank Top junction you will get a transfer to your accommodation in the surrounding area.

Ascent: 700m / Descent: 600m

Overnight Clay Bank Top

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Wainstones Hotel | 3 Star | Hotel

Combining the service and facilities of a Silver Award Winning three-star hotel with the atmosphere of a Yorkshire country inn. The Wainstones provide a friendly and comfortable stay for walkers.

The Buck Inn | Inn

The Buck Inn is located in South Chop Gate. The owners extend a warm, friendly welcome at the Buck Inn. Set amidst the rugged splendour of Bilsdale, the Buck Inn offers all the traditions of an English country tavern. The inn provides comfortable accommodation, all guest rooms are situated on the ground floor with private access to the large car park to the rear of the building.

Day 4 Clay Bank Top to Roseberry Topping 15 miles / 23.5 km

A transfer will take you back to Clay Bank Top, where a steep climb awaits, leading you to Round Hill and the summit of Urra Moor which is the highest point on the walk. Walking across the moors provides for fantastic walking although watch underfoot as some of the paths can be boggy. The path slowly descends to Kildale passing many burial mounds and boundary stones from the past. From Kildale climb up Easby Moor to Captain Cooks Monument. You are then allowed to climb the eroded sandstone stump of Roseberry Topping before heading downhill to overnight in Newton-under-Roseberry just off the path.

Ascent: 540m / Descent: 700m

Overnight Newton-Under-Roseberry

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Kings Head Inn | Hotel

A quintessential country pub with rooms in picture-postcard Newton under Roseberry, The King’s Head Inn is your gateway to Captain Cook Country. Beneath iconic Roseberry Topping, the inn has a is surrounded by peaceful countryside and forests

The Treebridge Hotel | 4 Star | Hotel

This family-owned hotel has an enviable reputation spanning over 20 years and is highly-regarded in the region for providing an extensive menu of locally-sourced food.

Day 5 Roseberry Topping to Saltburn-by-the-Sea 12 miles / 19 km

The walk continues through farmland, woodland and a riverside path that leads you to the coastal town of Saltburn-by-Sea where you leave the moors behind and prepare for cliff-top walking along the coastal section.

Ascent: 450m / Descent: 545m

Overnight Saltburn-by-the-Sea

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

The Spa Hotel | Hotel

The family-run Spa Hotel is an imposing sight, boasting unrivalled panoramic views of Huntcliff, the North Sea and beautiful surrounding countryside.

Ensure you book a table at their recently refurbished restaurant. We recommend timing it with the sunset!

Victorian Guest House | Guest House

Welcome to the Victorian guesthouse in the heart of Saltburn and only a five-minute walk from the beach. Features of the rooms include polished floorboards, original water colours, Victorian brass beds, and an open fireplace.

Day 6 Saltburn-by-the-Sea to Whitby 20 miles / 32 km

From Saltburn, the walk now hugs the coastline to Filey. You climb up Hunt Cliff and walk along dramatic sections, passing Rock Cliff (the highest point in the east of England). The path then descends to the pretty village of Staithes with its fleet of Cobles (flat-hulled fishing boats from Viking origin). More dramatic coastal paths take you to Whitby with its picturesque harbour and town steeped in history. High above the town are the remains of Whitby Abbey.

Ascent: 595m / Descent: 600m

Overnight Whitby

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Corra Lynn B&B | Bed and breakfast

The Corra Lynn B&B is a family-run B&B, located on the West Cliffs of Whitby. Each room comprises TV with free view, tea and coffee facilities, mini fridge, luxury soft towels and free WiFi.

Duke of York B&B | Bed and breakfast

The Duke of York is a charming inn that offers a comfortable Bed & Breakfast, and is located in the hart of Whitby at the bottom of the 199 steps. The B&B offers a warm and welcoming pub, which offers traditoonal pub food. There are 8 en-suite rooms in the Inn, that are dog friendlt. All of the rooms offer en-suites with showers, towels, bathmats, shower gel and handwash, and the rooms offer tea and coffee making facilities, a TV, hairdryer and suitcase rack.

Bagdale Hall | Hotel

Bagdale Hall is situated in the heart of Whitby. This atmospheric Tudor Manor House, which was built in 1516, offers guests the opportunity to relax in a historic house with a long and fascinating history whilst enjoying a high level of service and comfort.

Day 7 Whitby to Scarborough 21 miles / 33.6 km

Leaving Whitby pass some small beaches and rock wave cut platforms before arriving picturesque old fishing village Robin Hoods Bay. Perhaps stop to enjoy some lunch in one of the many pubs before continuing to Scarborough.

Ascent: 595m / Descent: 615m

Overnight Scarborough

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

The Cordelia | Bed and breakfast

The property has been beautifully restored and retains many original features. All 7 rooms are individually designed, decorated to a high standard and benefit from ensuites. With all the modern comforts you would expect to make your stay special such as top of range beds, luxury Egyptian cotton linen, thick fluffy towels, free high-speed WiFi, flatscreen UHD Smart TVs (with Netflix and other on-demand services) and stocked with Noble Isle toiletries.

The Waves | Bed and breakfast

There is no such thing as a standard room at The Waves. Each of their 7 rooms are unique – individually decorated and furnished to reflect the elegance of the late victorian building, with the added benefit of state-of-the-art Smart TVs and luxury beds.

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Bike and Boot Hotel | Bed and breakfast

A bright, modern hotel in the heart of Scarborough with all the facilities walkers could wish for including a boot washing station and drying area! Add to that comfortable and spacious rooms and a warm welcome and you'll be sure of a lovely stay in Scarborough!

Day 8 Scarborough to Filey. Transfer to Scarborough 8.5 miles / 13.5 km

Your destination today is Filey Brigg, the end of the Cleveland Way. Head out from Scarborough along more cliffside grassy tracks with a few ascents and descents. Be sure to savour this final stretch, looking back at the vibrant colours from South Cliff and reflecting on your completing the wonderful walking adventure!

Due to a lack of suitable accommodations in Filey, you will be transferred back to your accommodation in Scarborough.

Ascent: 165m / Descent: 165m

Overnight Filey

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

All Seasons | Bed and breakfast

All Seasons Guest House is a family-run bed and breakfast which has recently been refurbished to a high standard. This boutique guest house combines contemporary elegance and modern convenience with traditional warmth and hospitality. All Seasons is a 5 Star Gold awarded guest house.

Rutland West | Guest House

Rutland West is a restored Edwardian family run B&B ideally located between the beach and the town center.

Day 9 Onward Travel

THIS TRIP'S CARBON SCORE

This trip has a carbon score of 8kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 8kg is equivalent to 12 pints of local beer at the bar. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information on how we've carbon counted our trips.

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Other Information

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Is it for me? Accommodation & Meals Navigation What's Included

Included

Accommodation in carefully selected B&Bs, Guest Houses and Country Inns.
Breakfast each morning.
Door to door baggage transfer.
A detailed pre-departure information pack and access to the Macs Adventure Smartphone App
Emergency telephone support from our office in the event of a problem.

Excluded

Travel to the start or from the finish of the walk.
Lunches, dinners, snacks and drinks.
Lunches, dinners, snacks and drinks.
Personal Equipment.

Extras

Extra nights

When to go Travel & Transfers

Getting to the Start

By Air—The closest airport to the start of the walk is Leeds Bradford International, from here you can catch a train to Malton (55 mins) which is 16 miles from Helmsley, then either a bus or taxi to Helmsley.

By Train—Helmsley doesn't have its own train station and the closest station is 16 miles away at Malton. From the south, trains go via York to Malton, and again you take a taxi or bus to Helmsley. For National Rail timetables, see http://www.thetrainline.com/

By Car—If you plan on driving there is a car park on the north side of town and you can buy weekly parking tickets from the Tourist Information in the market square.

Getting from the End

There are frequent trains from Scarborough to York, from where there are good connections throughout the UK. If you need to head back to Helmsley, then you can catch the train to Malton, and then take a bus/taxi to Helmsley. For the moors and coastal section of the walk, there are frequent trains from the south to Saltburn, and you can catch a bus or a train back to Helmsley from Scarborough.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation.

At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase. Your booking includes transfer of 1 bag per person. It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.

Info & FAQ

Equipment

You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves, etc.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers for the activity and emergency evacuation and hospital care.