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Written by
Heleen Bosch
Heleen Bosch

Frequently Asked Questions about the Cleveland Way

There are some considerations when walking the Cleveland Way and our team of experts have come up with the questions they are most frequently asked. Have a read so that you are armed with all the information you need before setting off along this national trail of variety.

How fit do I need to be?

Depending on the chosen itinerary, the grade of this trip is either easy to moderate (11 Days), moderate (10 Days) or moderate to strenuous (9 Days). We have an itinerary for everyone's ability and are able to add extra nights where necessary to allow you to walk at your own pace. The path takes you from Helmsley in the heart of North York Moors National Park along rugged clifftop paths to Filey, on the coast. There are some uphill sections in the moors, where Urra Moor (1490ft above sea level) and Roseberry Topping (1050ft above sea level) are your highest points. The trail along the coast also has a few steep sections, especially near Robin Hood's Bay. This trip is perfect for the regular walker and no expert navigation skills are needed as the trip is very well waymarked from start to end. 

How do the baggage transfers work? 

Enjoy the ease of having your luggage transferred daily, allowing you to walk with just a light daypack and your packed lunch. Your bags will be transferred from your accommodation as per your itinerary and moved on to your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Please ensure that you do not bring more than one bag of 20kg, as if this occurs, the luggage transfer company will ask you to pay an additional fee (approx. £8.50 per day, per bag). This additional payment, should it be necessary, needs to be made locally to the driver and in cash.

When is the best time of year?

The route is shaped like a horseshoe, starting in the heart of North York Moors National Park before winding its way to the Heritage Coast. We offer the Cleveland Way from April to October as we believe that the trail is best enjoyed between spring and autumn. Traditionally, April and May have been the most popular time of the year to walk the route, as the theory goes that the weather is better. If you would like to see the moorland heather in bloom it is best to go during the months of August or September. The winter months bring windy and more unpredictable weather around the moors, this makes progressing along this route more difficult.

How do I get to Helmsley? 

The Cleveland Way is an accessible national trail with Manchester, Leeds and Newcastle being the nearest airports. The closest airport would be Leeds Bradford International from here you can catch a train to Malton (1hr) which is just 16 miles from Helmsley in a bus or taxi. Helmsley doesn't have its own train station, but Malton, York, Scarborough and Filey are the nearest ones. From the south, trains go via York to Malton, and again you take a taxi or bus to Helmsley. For National Rail timetables, see the Trainline website.

What personal equipment do I need? 

You will need good walking shoes (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack as well as sunscreen, a hat, and sunglasses. The trail can become muddy during or after rainfall, especially near the coast, so it is best to be prepared with the right footwear. This route involves a few climbs where you may find it useful to have your walking poles. As this route primarily follows the coast towards the end, we recommend windproof clothing to make it easier to progress.

If you would like to ask our team of specialists any questions about this fantastic national trail, please don't hesitate to contact one of our Destination Specialists, who will be more than happy to help and share their walking experiences!

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