The Cleveland Way: In a long weekend

Cleveland Way

Exploring the Yorkshire Coast via the Cleveland Way

Cleveland Way

The Cleveland Way is a 175 km National Trail running from Filey to Helmsley in Yorkshire, England. It is a truly specular way to explore both the Yorkshire Coast and the North York Moors National Park. The full trail will take you around 9 days complete, however, if you are short on time, the dramatic coastal section between Filey and Whitby can be completed on a long weekend. You will cover just over 55km on this weekend. Just between you and I, this is the most spectacular part of the path (in my opinion)

Route taken on the Cleveland Way National Trails
Coastal Route taken on Cleveland Way between Filey and Whitby

Day 1 / Filey to Scarborough

The shortest section of weekend allowing time to explore one of England’s most iconic and lively sea side towns. Although, the actual start of the Cleveland Way is a little difficult to find initially – once you starting spotting the National Trail Acorns its a doddle (Google maps will lead the way).

This section will give you taste walking along the cliff tops, the lofty path soon drops down in ancient forest that feels like its been there since the dawn of time, and finally taking you through outer villages into Scarborough.

Coastline following the Cleveland Way

Once you have arrived in Scarborough. Pop into the Grand Hotel for a pint on the viewing deck out the back. The Grand hotel is not as pretty as once was, the view from the terrace is the best in town. Watch out for the seagulls from above though, their aim is oddly very good. ha!

Pint with a view. At the Grand Hotel, Scarborough

Scarborough is the quintessential British seaside town. There is plenty to do here. If the weather is warm, take a dip in the North Sea. Wander along the seafront, and sample some of the freshest seafood in this part of the UK. There are classic arcades with penny drops and a small fairground. Pop up the hill to Scarborough castle with excellent views in all directions. In the evening, catch a show at the open-air theatre. There is certainly plenty to keep you busy for the rest of your day here.

Crab Post, Scarborough, Cleveland Way

Day 2 / Scarborough to Robin Hood’s Bay

Bathing boxes at North Bay beach, Scarborough

This 9-ish mile section is the most beautiful, but be warned it is also the most physically taxing. You will be cursing every set of stairs you see for at least a week. Setting off from Scarborough, you round the base of Scarborough castle and past the colourful bathing boxes at North Bay beach. At the end of the beach, (and past SEAlife) the climb to the clifftops commences. Once you reach the top you’ll be rewarded with views back to Scarborough. From here, you’ll pass miles of canola fields (they are in full bloom during April / May) on your left, to the right you’ll have uninterrupted views of the North Sea.

As the goes: ‘what goes up must go down’ and then up again and then down again. You’ll be led down into secret coves, and then up again past the ruins old military lookouts. There are multiple times during this leg, that will leave you speechless.

After a couple of hours, you’ll arrive at Ravenscar glimpsing Robin Hood’s Bay in the distance. Grab a cup of tea or my personal fave hiking treat – A solero!

Onwards! The scenery is this section is truly special and encompasses exactly what you’d expect the Yorkshire Coast to be.

My fave treat on a sunny day – the might Solero!

Shortly, you’ll arrive in Boggle Hole (possibly the best named place in Northern England). Stop here for a late lunch, at the Boggle Hole YHA (Its pirate-themed by the way) for a hearty meal and a cold pint.

Boggle Hole, best place name in all of the UK?

Departing Boggle Hole, you’ll back up to the cliff tops and onwards to Robin Hoods Bay, at this point your legs will be arguing with you but carry on its worth it.

Robin Hood’s Bay

Shortly, you’ll arrive at Robin Hood’s Bay, this charming historic villages is full of small winding alley ways that you can easily visualise fisherman and smugglers lurking about here hundreds of years ago. There are plenty of cafes, pubs, restaurants to refuel after this arduous leg – so rest your weary bones overnight here.

Day 3 / Robin Hood’s Bay to Whitby

Departing Robin Hood’s Bay

Depart Robin’s Hood Bay early – and you’ll be treated with beautiful and (people free) views and you walk out of town, The morning light just adds a little something special to the scene.

This section is much shorter than the previous days and definitely not as strenuous either.

Whitby Abbey / Fish and Chips /

On approach to Whitby, You’ll see Whitby Abbey in the distance, well before you see the town itself. One of the most iconic ruins in the region, once a monastery it was home to (at different times) both for Christian and Benedictine monks. Did you know: it was actually the inspiration for Bram Stoker’s ‘Dracula’

Whitby Abbey

Whitby Abbey, is well worth a visit if you have the time. Entry to the Abbey is around £9 or if you are member of English Heritage, entry is free.

Leaving the Abbey and heading into town, you’ll spySt Mary’s Church on the right. Famously, access to the church is via 199 steps from the town. However, you find yourself going down these instead of up 🙂

199 stairs to St Mary’s Church, Whitby. Travelling in the right direction – Down.

Now you have arrived in Whitby town itself – take some time to wander around this truly historic place. It should be Lunchtime when you arrive, so its definitely time to sample the Fish and Chips, Whitby is so famous for

Scampi and Chips, the perfect way to end a walk. Don’t forget the pickled onion!

Your arrival in Whitby brings you to the end of this short section of the Cleveland Way. It’s a fantastic introduction to the Yorkshire Coast, and hopefully, it will leave you wanting to return to explore the region further.

When to go

Spring, early Summer, and early Autumn. The weather is a lot of kinder but avoid bank/school holidays. Also, do check the weather before setting off, you will be walking on cliff tops and so the less wind, the more pleasant and safer experience you will have.

Accommodation on the Cleveland Way

The Yorkshire Coast and the towns and villages along the Cleveland way have a variety of accommodation options from charming bed and breakfasts to hotels there is something to suit all tastes and bugets. Click on the links below to check ou the options available to you.


Robin Hood’s Bay


Transport – Getting to and around the Cleveland Way

To get to Filey, jump on any train heading to Scarborough from York, Leeds, or Hull

The X93 bus from Scarborough to Whitby, also services Robin Hood’s bay. The most current timetable can be found here. If you intend to travel in either direction on a Sunday do check the timetable carefully as services are very few and far between.

Top Tips for the Cleveland Way

  • Bring a sunscreen and a hat (Although northern England is not the warmest of places you will get sunburnt) so slip, slop, slap.
  • Wear proper hiking boots: Trainers will simply not do for the terrain you will be covering, so ensure you have good ankle supporting boots.
  • Book you accommodation in advance. This part of Yorkshire is very popular during both summer and bank holiday weekends, most (reasonably priced) places will be sold out weeks in advance.
  • Check the weather. If the wind is up this will make for a very unpleasant experience indeed.

For more information on the Cleveland Way check out the National Trails Website

If you enjoyed this post – please take a look at my 3 part Hadrian’s Wall Adventure