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Trail Facts

Total distance: 110 miles (176 km)
Duration: 8 nights, 7 days running
Minimum daily distance: 11 miles (17.5 km)
Maximum daily distance: 21.5 miles (34.5 km)
Code: R-CLEVW4

Grade: Moderate
Season: 14th 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 Clay Bank Top(T). 11 miles (17.5km)

Day 4: Clay Bank Top(T) to Captain Cook's Monument(T). 11.5 miles (18.5km)

Day 5: Captain Cook's Monument(T) to Staithes. 21 miles (34km)

Day 6: Staithes to Robin Hood's Bay. 18.5 miles (29.5km)

Day 7: Robin Hood's Bay to Scarborough. 14.5 miles (23km)

Day 8: Scarborough to Filey. 12 miles (19km)

Day 9: 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

The charming 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. A lovely short walk/run from here visits the Lady Chapel and Mount Grace Priory, an attractive 14th century Carthusian monastery.

Staithes is an attractive little fishing village with an interesting exhibition on Captain Cook while another popular choice for an extra night is Robin Hood's Bay, which is within easy reach of Whitby. Here, there is an attractive harbour, atmospheric ruined abbey, Captain Cook Museum, Lifeboat Museum, Whitby Museum and St Mary's Church. The interior of this intriguing church was altered in 1612 to resemble the lower deck of a wooden sailing ship.

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?

  • 8 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 major city and international airports are Leeds-Bradford, Manchester and Durham Tees Valley.


The nearest rail stations to Helmsley are either Malton (about 16.5 miles away) or York (about 25 miles away). There is a rail station at the end of the trail (Filey).

Trains run from London Kings Cross station to Malton. From there a bus/taxi will be required to Helmsley.


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 of the trail, is to take a train from Filey to Malton. From there a bus/taxi will be required to Helmsley.

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