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Trail Facts

Total distance: 110 miles (176 km)
Duration: 7 nights, 6 days running
Minimum daily distance: 12 miles (19 km)
Maximum daily distance: 22.5 miles (36 km)
Code: R-CLEVW3

Grade: Moderate
Season: 24th March - 31st October
Start of holiday: Helmsley
End of holiday: Filey


Day 1: Travel to Helmsley where your first nights accommodation has been booked

Day 2: Helmsley to Osmotherley. 21.5 miles (34.5km)

Day 3: Osmotherley to Captain Cook's Monument(T). 22.5 miles (36km)

Day 4: Captain Cook's Monument(T) to Saltburn-by-the-Sea. 12.5 miles (20km)

Day 5: Saltburn-by-the-Sea to Whitby. 20.5 miles (33km)

Day 6: Whitby to Scarborough. 21 miles (34km)

Day 7: Scarborough to Filey. 12 miles (19km)

Day 8: Depart from Filey after breakfast

The itinerary above shows our preferred overnight stops, but if accommodation is not available at any one of these locations, we may alter the itinerary slightly.

Extra nights / rest days

If you would like to add an extra night into your holiday to explore the locations along the Cleveland Way, or to take a break from running for a day, then there are plenty of interesting locations to choose from along the trail.

The thriving village of Osmotherley, with its neat stone cottages huddled around its green, ancient market cross and stone table where John Wesley preached during one of his sermon tours, is a popular choice for an extra night?s stay. Not only are there a number of shops and pubs to enjoy, but a short walk from here visits the Lady Chapel and Mount Grace Priory, an attractive 14th century Carthusian monastery.

The Cleveland Way also visits the characterful town of Whitby, with plenty of attractions to occupy you during a rest day. Not only is there an attractive harbour to visit, several fascinating museums to explore and the infamous ruined abbey atop a hill in which Dracula was said to have resided, but there is a variety of shops and some of the most famous restaurants and fish and chip shops in the UK. There are also plenty of sports shops, leisure centres and swimming pools in Whitby, as well as a couple of sports massage clinics if you?re beginning to feel a bit sore from your run.

If you fancy somewhere livelier however, you could consider the bustling seaside resort of Scarborough, where you can soak your feet in the sea, go rock-pooling or even try your hand at surfing, with many sports shops and leisure centres dotted around the town. There is a wide range of attractions to suit everyone; whether you want to relax on the beach, challenge your friends to a game of miniature golf, enjoy delicious locally-produced food or explore the surrounding trails on foot or by bike hire, Scarborough promises to keep you entertained throughout your stay.

What's included?

  • 7 nights accommodation in en-suite rooms with private bathrooms (where available) in selected hotels, inns and guesthouses along the trail.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night, town plans, information about facilities and places of interest along the trail and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.
  • Emergency assistance.

Travel Information


The most convenient international airports are Leeds-Bradford Airport and Durham Tees Valley Airport.


The nearest rail link to Helmsley is Malton. There is a railway station at the end of the trail (Filey).

For London - There is a frequent train service from London Kings Cross to Malton.


For advice on driving to the start of the trail, please visit which has a very useful route planner.

Returning to the start

The easiest way to return to the start is to catch a train from Filey to Malton. Then take a taxi to Helmsley.

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