Cleveland Way Short Break
Sample the Cleveland Way on a short self-guided walking holiday: the perfect weekend getaway. Accommodation, luggage transfer and custom holiday pack included.
Cleveland Way Short Break
https://www.contours.co.uk/cleveland-way-short-break
A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.
From £390 per person
Take a self-guided walking holiday along the Cleveland Way, a walk of stunning contrasts. Beginning in the old market town of Helmsley, the Cleveland Way traverses the western escarpment of the North York Moors to the coast at Saltburn-by-the-Sea, before following the Cleveland Heritage Coast to the Victorian town of Filey.
While walking through the Moors, the trail traverses woodland, green dales and heather moorland. This section is packed with historic interest, including the iconic White Horse of Kilburn. The coastal section then follows high cliffs, sandy bays and wooded wykes. Picturesque fishing villages pepper the trail, as well as the famous port of Whitby. Overall, the Cleveland Way is an incredible walking trail filled with intrigue and beauty.
Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.
We also organise trail running holidays along this route. Find out more.
From £390 per person
This short break takes in the first stretch of the Cleveland Way along the southwestern edge of the North York Moors. Beginning at the market town of Helmsley, the trail traverses a mixture of wooded dales, open fields and cliff edges, visiting such interesting landmarks as the ruins of Rievaulx Abbey and Roulston Scar, where the head of the Kilburn White Horse can be reached.
After passing through Sutton Bank, the trail follows more clifftops and high moorlands filled with heather, before reaching the stone village of Osmotherley and admiring views over the Gormire Lake below.
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £390 |
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £390 |
Travel to Helmsley where your first night's accommodation will be booked
Helmsley to Sutton Bank(T). 10.5 miles (17km) / 1421 ft (433 m) ascent
Sutton Bank(T) to Osmotherley. 12 miles (19km) / 1004 ft (306 m) ascent
Depart from Osmotherley after breakfast
This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.
Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.
The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.
Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.
Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:
You can add rest days at any of the overnight stops:
Following the western edge of the North York Moors and enjoying spectacular views stretching out towards the distant Pennines.
Spotting gliders from the vantage point at Sutton Bank, with outstanding views over the Vale of York.
Strolling peacefully around the quiet village of Osmotherley at the end of your holiday.
You can add rest days at any of the overnight stops:
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Dog friendly