Cleveland Way - 10 Days & 9 Nights

From $1,590.00
10 Days & 9 Nights
Read 33 reviews

Cleveland Way - 10 Days & 9 Nights

  • 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.


Day 1 Arrive Helmsley Day 2 Helmsley to Osmotherley 22 miles / 35.2 km Day 3 Osmotherley to Clay Bank Top 12 miles / 19.2 km Day 4 Clay Bank Top to Roseberry Topping 13.75 miles / 22 km Day 5 Roseberry Topping to Saltburn-by-the-Sea 10.25 miles / 16.4 km Day 6 Saltburn-by-the-Sea to Whitby 20 miles / 32 km Day 7 Whitby to Robin Hood's Bay 7 miles / 11.2 km Day 8 Robin Hood's Bay to Scarborough 13 miles / 20.8 km Day 9 Scarborough to Filey 10 miles / 16 km Day 10 Onward Travel

Other Information

Is it for me? Accommodation & Meals Navigation What's Included When to go Travel & Transfers Info & FAQ

Why Macs

Reasons to believe in Macs Adventure:
The biggest choice

The biggest choice

Self-guided hiking & biking is all we do - we have over 500 tried & tested trips.
Our Heritage

Around since 2003

We’re still founder led & the world’s number one self-guided operator with mountains of experience.

18,000+ customer reviews

Plus, with a Feefo Platinum Service Award & a British Travel Award, you know you're in good hands.
Positive Impact

Positive impact

We use independent suppliers to support communities along our routes, as well as work with organizations to help maintain & restore paths.
The Macs Way

At Macs, we don’t do tour buses, groups, or guides. Instead, we give you the freedom and confidence to have your own self-guided hiking or biking adventure

It's active travel, led by you.

Travel on your terms

You choose your departure date and who you travel with, we do the rest.

The people behind your journey

We sort accommodation and luggage transfers and provide your route in an easy-to-use app.

Here when you need us

We give you everything you need to travel independently but we're here 24/7 if you need us.

Achieve something

Getting from A to B under your own steam is intensely rewarding. With Macs, you'll see the world, and yourself, differently.

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