Cleveland Way – 11 nights / 10 days walking

About this trail

Your Cleveland Way walk combines the spectacular beauty of some of England’s finest moorland scenery with enchanting coastal views.

You start your holiday from the attractive market town of Helmsley, before heading across the rugged heather moorland of the North York Moors National Park. You first reach the coast at Saltburn-by-the-Sea before continuing along the breathtaking North Yorkshire coastline to Filey, passing quaint fishing villages and lively coastal towns.

The Cleveland Way runs through the famous smuggler’s village of Robin Hood’s Bay and the seaside resorts of Scarborough and Whitby. The latter is a charming coastal town and home to Whitby Abbey, the inspiration for Bram Stoker’s Dracula.

Officially opened on 24th May 1969, the Cleveland Way was the second recognised National Trail in England and Wales.

Terrain and navigation

The Cleveland Way is well signposted and follows well-trodden paths along its route. There are occasional sections that involve some steep inclines, not least the ups and downs along the coastal section, but anyone who is reasonably fit can walk the route. Its highest point is on Urra Moor which features prehistoric remains.

Route elevation

Highest point: 454 metres
Total ascent / descent: 4388 metres / 4433 metres

Included as standard in the price

The price quoted is per person and is based on two people sharing a room. It includes:

• Carefully selected, en-suite bed and breakfast accommodation*
• Daily luggage transfers to your accommodation**
• All the necessary maps and guidebooks for your walk
• Route notes and maps detailing how to find your B&B at the end of each day
• The cost of any transfers that are required from the route to your accommodation if we are unable to book you into a B&B within easy walking distance of the trail
• Information about any special facilities offered by your hosts (eg hot tub or licensed bar)
• Suggestions and contact details for places for an evening meal each day
• Telephone support if required
• Advice from our team on travel to and from the start and end of the trail.

*En-suite is always chosen unless all options are booked out, in which case private bathrooms are sought. Customers are always consulted about non-en-suite options before details are finalised.

**Standard package includes one piece of baggage per walker, up to a maximum weight of 20kg. Additional bags can be transferred but incur an additional cost. Please enquire if you need this service.

Packed lunches and evening meals

The cost of these is not included in our standard package. All the accommodation providers we use offer packed lunches to keep you well fed during your walk. Payment is made directly to your hosts. Similarly, if you have an evening meal either at your accommodation or another local establishment, you pay them directly for it.

Optional extras that can be provided by Discovery Travel

Discovery Travel specialises in providing completely tailor-made services to our clients. This means that if our standard published itineraries do not suit our customers’ needs, we are always happy to discuss ways in which we can adjust accommodation, shorten or lengthen itineraries and distances to make for the perfect trip.

We also offer the following services to make for a seamless holiday:

• Transport to and from the start and finish of a trail
• Airport transfers
• Minibus and driver service, in particular for large groups where multiple accommodations are required each night and transfers are frequently required at the end of the day’s walk

If you are interested in any of the above or have any particular requirements, please do contact us to discuss your needs.

Make more of your break

If you would like to pause during your walk and explore one of the overnight locations for longer, you are free to select and add extra days to your holiday at any of your overnight stops. Prices for extra days are quoted above and will be added to the total cost of the holiday. If the itineraries on our website do not quite meet your requirements please do get in touch to arrange a bespoke trip.

Below are some suggestions for good places to spend an extra day or so.

Whitby

Whitby is an ancient and enchanting port town steeped in history. There are many visitor attractions that are connected to the town’s fascinating past, such as the Captain Cook Memorial Museum, where you can learn about the famous explorer’s life in the port town. Climb the 199 steps to Whitby Abbey, counting as you go, and explore the beautiful ruins which tower over the town and provided the backdrop for many of the scenes in Dracula. A keen shopper will find much of interest in Whitby’s boutique shops and quirky streets, home of the unique Whitby jet jewellery and other fascinating items.

Scarborough

As well as its two iconic beaches, the traditional seaside resort of Scarborough is home to the Rotunda Museum – one of the world’s first purpose-built museums. Find out more about the geology and fossils of the local coastline and come face to face with specially commissioned reconstructions of what marine life was like millions of years ago. If you prefer to be outdoors then you can climb Oliver’s Mount, a large wooded hill rising to 500 feet above sea level that provides a wonderful view of Scarborough, after taking a trip on one of Scarborough’s two cliff lifts that date from the late 1800s.

When to go

The weather in the UK and on its moors and coast can vary hugely so be prepared for all weathers whatever time of the year. April, May and June are when everything comes to life so it is very green, wild flowers are abundant and blossom abounds. July and August tend to be the warmest months and the time when the Heather is at its best. September tends to be one of the most pleasant times in the countryside and is quieter as most people with children have finished their holidays. By October the days are getting shorter and the weather can be much more changeable.

Getting to and from the trail

By Air: The most convenient airports are Leeds-Bradford Airport and Teesside Airport.

By Rail: There is a regular train service from London Kings Cross to York, from where you can catch a local train to Malton and travel onwards by bus to Helmsley. Filey  has a train station. For train times visit National Rail Enquiries.

By Bus: Buses stop in Helmsley. You can find details on getting to Helmsley using Google Maps. Click on “directions” in the left hand tab and enter your starting point.

Got a question about travel? If you need any help with travel to and from your walk please get in touch with Discovery Travel.