Cleveland Way

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A challenging walk from Scarborough Castle to Whitby Abbey...

Book your experience
Available dates:
  • Duration

    Single Day Event
  • Accommodation

    Not required
  • Food

    None provided
  • Difficulty Level

    3 Three

To celebrate the 50thanniversary of the North York Moors National Park’s flagship long distance Cleveland Way National Trail, we launched a 24-mile walking challenge along a stunning coastal stretch of the Cleveland Way.

Setting off from Scarborough Castle our challengers will follow the trail northwards passing some of the most iconic sights of North Yorkshire’s coast and accompanied by stunning seascapes all the way until the finish at Whitby Abbey.

This is the perfect new challenge for those of you looking to take part in a sponsored walk or indeed just for a personal challenge.

In a nutshell:

  • Feel elated after completing a new challenge that is the coastal equivalent of Yorkshire’s Three Peaks.
  • Soak up the superb scenery and enjoy the company of fellow challengers
  • Raise a glass in honour of completing the challenge with a free pint of beer given to all finishers by Whitby Abbey.

Castle to Abbey Challenge Dates:

  • Saturday 25th April 2020
  • Saturday 30th May 2020
  • Saturday 18th July 2020
  • Saturday 26th September 2020

Walking the Cleveland Way

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Itinerary – route description

NB: This challenge is self-guided but we’ll be supporting you by providing transport between the start and finish and having vehicles at important junctions along the way.

We will also have first aid trained guides along the route and bringing up the rear.

At 7am registration opens at Whitby Abbey. Once everybody has registered we hop on the coach and drive to the start.

Walking the Cleveland Way

Route description

What better way to start a march than at Scarborough Castle, a prominent 12thcentury fortress where you can imagine Henry ll’s troops being given their marching orders.

From the Castle entrance you pick up the Cleveland Way heading north alongside the beach front before leaving the spa resort of Scarborough behind.

The undulating route winds its way up onto the cliff tops with open fields to one side and enticing seascapes to the other before entering National Trust woodland at Hayburn Wyke.

Walking the Cleveland Way

The name derives from the Anglo Saxon word Hayburn which means hunting enclosure by a stream and the Norse word Vik which means sea inlet. Wandering through the woodland all that makes perfect sense especially once you reach the star of the show, the waterfall that tumbles directly onto a pebble beach.

It’s worth having a breather here but with more great views up ahead don’t linger too long. Instead press onwards and upwards through the woodland to emerge into the open cliff tops once more.

Walking the Cleveland Way

A few more miles along you come to ‘the town that never was’ or Ravenscar, a hamlet which is hard to believe was once destined to be a rival spa town to Scarborough in Victorian times if the developers hadn’t gone bust. Today you’ll notice a few of the streets that were constructed and the old railway line as you pass the conveniently-located tearoom.

Further along another slice of Ravenscar’s history is discovered as you pass through the remains of the alum works, which were considered to be the World’s first chemical industry making an agent that fixed dyes in cloth making.

From here the path begins to descend gradually to Stoupe Beck and then the delightfully-named Boggle Hole, so-called because goblins were said to inhabit one of the caves near the sandy cove. Here the YHA’s Quarterdeck café with its view out to sea provides an enticing prospect for re-fuelling.

You then leave Boggle Hole through a woodland path and back onto the headland where you’re rewarded with fine views particularly when the village of Robin Hood’s Bay comes into sight.

Walking the Cleveland Way

As you reach the village the Cleveland Way weaves its way through the cobbled alleyways and tiny snickets between the cottages where you can easily imagine what life was like in the heyday of smuggling.

There’s plenty to hold you here but press onwards knowing you’re on the final leg of the journey. Pass above Saltwick Bay and you’ll see the remains of the shipwrecked fishing trawler the Admiral Von Tromp near the rocks.

Once past Saltwick Bay and with the outline of Whitby Abbey acting as a beacon, all that remains is a 20-minute stride out to reach the finish.

Here Whitby Brewery which is conveniently located alongside the Abbey will welcome you into its tap room where a celebratory pint will be poured in your honour and those thoughts of ‘I so need a drink’ can become reality!

Walking the Cleveland Way

Good to know:


Registration is in Whitby and opens at 7am.

Whitby Brewery
East Cliff
YO22 4JR

What’s Included:

  • Full pre-event support from training advice to kit lists.
  • Supported challenge with checkpoints and support vehicle.
  • First aid trained guides along the route to help and assist when needed.
  • Coach travel from registration to the start in Scarborough.
  • Celebratory drink at Whitby Brewery.

The Basics:

Age Limit:  You must be over 14 to take part in this challenge, anyone under 18 must be accompanied by an adult. There is no upper age limit.

Dogs:  I am afraid dogs are not allowed on this trip, unless they are registered assistance dogs.

Solo Travellers:  This trip is perfect for solo travellers and although couples and small groups of friends are always welcome the majority of people do attend on their own.

Useful Links:

Kit lists – You can view our kit lists here…

For important information on what’s included with our standard trips, such as what food we supply, arrival times and answer to our most commonly asked questions please visit out our FAQ’s page

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Whitby Brewery
East Cliff
YO22 4JR
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What our members have to say...

  • “I didn’t really know what to expect on my first ever walking holiday and wasn’t very prepared if truth be known – lesson to all read the essential kit list especially waterproofs! It was great fun and what a lovely group of supportive and encouraging people, especially Gareth who did a great job looking after us all. I must admit at times I found it a bit challenging but what a great sense of achievement when we reached the top of the mountains (hills) I will definitely do this again.
    Member Since 2016
  • My first Large Outdoors and (Ulster & the Giant's Causeway Walking Weekend) Irish experience was absolutely fantastic. Everything was organised perfectly and Gareth is a joy to be around. I loved every minute and will definitely book myself onto another trip. #toldallmyfriendstheyhavetocome
    Member Since 2018
  • Well, for a non-walker it was certainly challenging but my word was it exhilarating! The feeling of achievement after every day, was just fabulous. The group we went with were all strangers on day one, but firm friends by the end of the week. The comradery on some of the tougher walks, helped me to the top…..and wow what views. Anyone thinking of doing it - don’t worry….just go for it!
    Member Since 2016
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