Walking the Cleveland Way?

Let Sherpa guide you...

Before your Walking Holiday Sherpa helps you plan your itinerary and books all of your accommodation

We help you plan your itinerary and book all of your accommodation

During your Walking Holiday Sherpa collects your bags every morning and drops them off at your next stop the same day

We collect your bags every morning and drop them at your next stop the same day

The baggage transfer and accommodation booking service for the Cleveland Way

Whitby on the Cleveland Way The Cleveland Way is one of twelve designated National Trails. Starting at the historic market town of Helmsley the 110 mile walk skirts the upland ridge on the edge of the North York Moors National Park before reaching the coast to end at Filey. It is often described as two walks in one: The first of beautiful heather moorland and the second of outstanding coastland.

The purpose of Cleveland Way is to provide you with a means to plan your own itinerary, book your accommodation and/or take advantage of services offered along the route. A factsheet is provided to help you plan your itinerary whilst a chat bulletin board will allow you to ask your unanswered questions and draw upon the advice of those who have previously undertaken the walk. You might also like to read our FAQ, especially if you're a novice walker.

Happy walking.

Choose either...

Baggage transfer and accommodation booking for Cleveland Way walking holidays in Britain

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

Baggage transfer and for Cleveland Way walking holidays in Britain

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 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 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.