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image for Walking Event item typeThe Castle to Abbey Coastal Challenge at Cleveland Way - Filey

  • Welcome To Yorkshire Member

Walking Event, Sat 14 Sep 2019, £35

The Castle to Abbey Coastal Challenge

The Castle to Abbey Coastal Challenge


Next year is the 50thanniversary of the North York Moors National Park’s flagship long distance Cleveland Way National Trail.

To mark the milestone of the 109-mile trail, one of our favourites, we’re introducing 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 14th September 2019
Saturday 25th April 2020
Saturday 30th May 2020
Saturday 18th July 2020
Saturday 26th September 2020

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.

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.

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.

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.

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!

Good to know:
Registration is in Whitby and opens at 7am.

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 Travelers: This trip is perfect for solo travelers 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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Picnic site

Children welcome

Event details

Dates Times
Sat 14 Sep 2019

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North York Moors National Park Authority


Cliff Top,
North Yorkshire,
YO14 9HG



See location of Cleveland Way - Filey on Google mapsSee location on Google maps

Map reference: TA 119808  Lat: 54.21073 Long: -0.28567

From Filey follow signs to Country Park

Parking: with charge


  • Picnic sitePicnic site
  • Children welcomeChildren welcome