Matt and his friend, Kev, recently walked the 111 mile Cleveland Way in 4 days.  A lot of miles to cover in a short amount of time and Matt's feet didn't fare that well!  I asked Kev to write something to share with others who might be thinking of doing something similar.  So thank you, Kev, for keeping Matt company and writing the below for me...... 

These were the thoughts I had when speaking to my friend Matt, who, along with his wife Sian, owns these two beautiful historic holiday cottages.

My family and I had booked a few days’ stay in Sherwood House, and so, Matt and I devised a plan to spend four days walking the Cleveland Way before meeting my family in Robin Hood’s Bay.

The Cleveland Way is a 111-mile National Trail starting at the beautiful market town of Helmsley and finishing in the popular coastal town of Filey. 

It is fully waymarked with the traditional acorn National Trail symbol and traverses the North Yorks Moors before joining the east coast at Saltburn-by-the-Sea and turning south along the coast path through pretty coastal villages and towns including Whitby, Robin Hood’s Bay, and Scarborough.

Day 1 - Helmsley to Lordstones (28 miles).

The walk starts with a flat or gently undulating path through pretty wooded areas and along quiet roads, passing through the villages of Cold Kirby and Hambleton before reaching Sutton Bank, where there is the option to add an out-and-back section to White Horse. 

The visitor centre at Cleave Dyke is the perfect lunch stop. Here you can find a café and public toilets, and just a little way past you'll find "The finest view in England", although we'd argue there are finer views on the Cleveland Way.

A few miles further on, we made our way onto the more remote moorland where we were rewarded with views of the rolling hills clothed in different shades of purple heather. The village of Osmotherley offers the opportunity to top up on snacks at the village store or quench your thirst at one of the excellent pubs.

A short distance beyond Osmotherley, in Arncliffe Wood, the Cleveland Way meets the Coast to Coast National Trail. The trail then passes through the village of Hollin Green before climbing over Round Hill, Gold Hill, and the high point on Carlton Moor before descending to the remote but inviting Lordstones campsite, where you'll find a café and shop, as well as toilet and shower facilities.

Day 2 - Lordstones to Saltburn-by-the-Sea (31 miles).

This is the most remote section of the whole Cleveland Way, with minimal opportunities to top up water and food supplies. Make sure to leave Lordstones with plenty of both.

Whilst remote, this is also the most picturesque section of the trail, which affords views for miles on a clear day from each of the many hilltops. We were fortunate to have a dry, sunny day to enjoy the stunning beauty of the moors. Just remember not to be too distracted by the views and miss the sharp left turn at Bloworth Crossing, where the Cleveland Way separates from the Coast to Coast path. We didn't make this mistake, honest!

The small village of Kildale provides well-maintained public toilets at the unstaffed railway station, an opportunity to top up water bottles before heading uphill to Captain Cook's Monument on Easby Moor.

A little further up at Highcliffe Nab, we looked down over the sprawling town of Guisborough. The clear sky also rewarded us with our first view of the sea on the horizon.

Pubs at Slapewath and Skelton Green provide opportunities for well-earned food and refreshments, whilst Skelton and Saltburn have several supermarkets and takeaway options depending on the time of your arrival. There are also plenty of B&Bs to choose from.

Alternatively, like us, you could choose to wild camp on the coast path. Just remember, arrive late, depart early, and leave no trace!

Day 3 - Saltburn-by-the-Sea to Robin Hood’s Bay (27 miles).

The coastal section of the Cleveland Way traverses the clifftops between villages and towns, where the path drops to sea level before rising steeply back up again.

The village of Skinningrove has a lovely sandy beach and a coffee van, perfect for a mid-morning stop. Next, you’ll pass through the village of Boulby, home of a mine producing half of the UK's potash output.

The picturesque fishing village of Staithes is a place to stop for a while and enjoy the relaxed vibe. Be sure to visit the Sea Drift Café on Church Street and treat yourself to a portion, or two, of Coble Cake, the oldest family dessert in Yorkshire.

The villages of Runswick Bay and Sandsend have sandy beaches, popular with visitors from near and far. Here we enjoyed a cold glass of Coca-Cola overlooking the bay.

A couple of miles beyond Sandsend is the busy harbour town of Whitby. Stopping for fish & chips and ice cream is optional but strongly advised. You'll need it to fuel you up the 199 steps to the Abbey and back onto the clifftop path for the final 6.5 miles to Robin Hood’s Bay.

On arrival at Robin Hood’s Bay, I checked into Sherwood House for a long bath and a great night's sleep in a king size bed.

Day 4 - Robin Hood’s Bay to Filey (25 miles).

After a comfortable night's sleep, you'll be fully refreshed to walk the final 25 miles of the Cleveland Way to Filey.

Boggle Hole YHA and Ravenscar National Trust cafés provide opportunities to rest and refuel, whilst at the small bay at Hayburn Wyke we found a peaceful place to sit and listen to the waves lapping onto the shore.

The busy town of Scarborough, with its plethora of cafés, pubs, and takeaways, is a perfect lunch stop before the final 8 miles to Filey.

The Cleveland Way officially ends at Filey Rigg, where the coast path becomes the Yorkshire Wolds Way. Here we took a moment to soak up the view and reflect on our journey before the mile-long walk into town.

From Filey, it's an easy journey back to Robin Hood’s Bay via train from Filey to Scarborough, and the X93 bus from Scarborough to Robin Hood’s Bay. A celebratory pint in the Victoria Hotel is optional before the walk down the hill to Sherwood House.

A massive well done to both of them.  If you have any questions on the walk please get in touch.  Matt will be more than happy to answer them.

Matt's next challenge next year - The Coast to Coast.

Thank you again Kev for your words.