The Cleveland Way 

The 109-mile Cleveland Way National Trail takes you through the breath-taking heather moorland of the North York Moors National Park and along one of the North East’s finest coastlines as it makes its way from Helmsley to Filey.

It officially opened back in May 1969 and was the second recognised National Trail in England and Wales. 

The well-signed route can be done from either direction – whichever way you decide to put your best foot forward, you will be rewarded with stunning views, beautiful towns and villages, and wonderful company from fellow walkers along the way. 

Don’t be put off by the scale of the Cleveland Way, you don’t have to tackle it in one go. Think of it as a feast for the senses that you can dine on at your leisure.

Check out the full route and take your pick by breaking it up into bite-size pieces so you can enjoy a weekend walk to blow away the cobwebs. Just pack a flask, decide on your sandwich, lace up your boots and you’re ready to go. 

Whitby to Robin Hood’s Bay

The seaside resort of Whitby is the starting point for a seven-mile walk along the Cleveland Way to the old fishing village of Robin Hood’s Bay.

Ahead of the walk, there's plenty to see and do in Whitby. Of course, you could treat yourself to a portion of fish and chips from one of the many restaurants and takeaways before hitting the road.

If you want to have a quick warm-up before your walk, take the famous 199 steps up to St Mary’s Churchyard and soak up the views of Whitby Abbey, the inspiration for Bram Stoker’s Dracula. The monastic ruins of the Abbey stand proud on the headland and offer panoramic vistas across Whitby. 

Here the walk to Robin Hood’s Bay is well signposted and you can get going. Meander along the clifftop route with the sea to your left. As you make your way, after a couple of miles you can pause and take a look at Whitby high lighthouse and foghorn station.

Today, the lighthouse offers holiday accommodation and the foghorn is privately owned. Back in the day, when the fog rolled in, the foghorn would have sounded loudly to warn of rocky coastlines or to caution boats of the presence of other nearby vessels.  

The beauty of walking a route such as the Cleveland Way is that, even if you are taking a solo trip, you can enjoy the camaraderie of others who have chosen to do the same.

Cheery hellos from passing walkers are standard, along with shared snippets of wildlife spotted or helpful heads up for muddy bits ahead! 

Here, daydreamers and dawdlers walk alongside roamers and ramblers who are all equally at home. No pressure to get anywhere fast, just the anticipation of the reward of a well-earned cuppa or pint in one of the cafes and pubs in Robin Hood’s Bay when you reach your destination.

Much of the path is relatively easy underfoot but, depending on the time of year, it can be muddy and slippy in places.

Parts of the route involve steepish ups and downs with a couple of stepping stone stream crosses along the way. Just take your time, watch your feet in places and enjoy. 

The ever-changing seascape means you never tire of the view and you can get more than a daily dose of vitamin sea on your walk. Take your binoculars as it's not too uncommon to spot whales and dolphins along the way. Closer to the path, you can enjoy the seasonal flowers and shrubs as well as all the birdlife that it attracts. 

The walk down into Robin Hood’s Bay takes you to the village which is a hugely popular tourist destination within the North Yorks Moors National Park.

Its small sandy beach and rock pools aplenty are a real draw all year round for young and old alike. Wander through the narrow, cobbled streets with hidden alleys and be transported back hundreds of years when it was a smugglers hideout and press gangs roamed the streets.

Don’t worry, there's no need to dodge pirates anymore. These days the village offers cafes, traditional pubs and restaurants where you can enjoy everything from fresh fish and ice creams to tea and cake in picturesque surroundings.

Soak up the history and heritage of the village at the Robin Hood’s Bay and Fylingdales Museum, situated in the old Coroner’s Room and Mortuary.

Entry is free and the small, perfectly formed museum is crammed full of displays, maps and artefacts showing what village life was like over the centuries.

Learn all about what was smuggled and what contraband may have been found hidden about the person of an old fisherwife. The museum is run by volunteers and it's always best to check ahead for opening times. 

Once you have rested and enjoyed all this small but historic village has to offer, you can decide your next move.

As the walk is linear, you can just retrace your steps back along the coast towards Whitby. However, if you want to enjoy more of the area’s scenery, there is the Cinder Track route back to Whitby.

Just follow the signs from Robin Hood’s Bay and off you go. Part of the Cinder Track is a disused railway and relics from bygone days can be spotted along the route.

If you have done enough walking for one day and decide it’s time to give your feet a rest, then hop on a bus back to Whitby. There's a regular service but it’s always best to check ahead for changes in seasonal timetables.

Walking the Whitby to Robin Hood’s Bay will whet your appetite to see more of the Cleveland Way. Just look at the route on a map, choose another section and plan your next day out walking.

Enjoy being in nature, whatever the weather, whatever the season. You won’t be disappointed. Happy walking!