Places to visit along the Cleveland Way

Inhale lungfuls of fresh sea air at Filey Brigg, your starting point on the Cleveland Way. Ripe for rock pooling, Filey Brigg’s striking headland stretches into Filey Bay. Go for a bracing stomp along Filey Beach, crowned “Beach of the Year” in 2018 by The Sunday Times. Admire its five miles of tawny-sand perfection and explore the intriguing Sculpture Trail.

Walk the Cleveland Way for 90 minutes (or hop in your car) to Cayton Bay, a sweeping bay that welcomes walkers, fossil hunters and four-legged explorers all year round. The beach is also popular with surfers and birdwatchers. Pause for coffee and snacks (bacon roll, perhaps?) with a view at The Salty Dog, perched on a clifftop above the bay.

Unfurl your map for Scarborough, a 15-minute drive or 1 hr 22 minute walk along the Cleveland Way. Discover glorious Scarborough Beach – aka the St Tropez of the North – and wander along the golden sands, admiring the children-topped donkeys. Collect shells, build sandcastles and enjoy your first portion of fish and chips: try award-winning Papa’s.

Swap waves for waterfalls at Hayburn Wyke, accessible by car in 17 minutes or on foot in just over two and a half hours. This secluded cove woos visitors with its beach, woodlands and waterfall; if you swerved fish and chips in Scarborough, pause for a peaceful picnic here. Look out for roe deer, badgers and foxes in the woods.

From Hayburn Wyke, follow the Cleveland Way to Robin Hood’s Bay, a 25-minute drive or three-hour hike. Once a popular haunt of smugglers, this fishing village is famous for its labyrinthine lanes and higgledy-piggledy houses. Have dinner and a pint in an atmospheric pub, before checking into The Pigsty, a quirky Landmark Trust self-catering stay, five minutes away by car.

Sea air equals increased hunger: have an alfresco breakfast at The Galley on the Quarterdeck, a tea hut takeaway with arguably the finest views on the North Yorkshire Coast. Enjoy creamy hot chocolate, freshly ground coffee, paninis, or a warming soup. The hut is open daily, weather-permitting, but also has a handy webcam so you can check conditions before coming.

Unleash your Gothic side in Whitby, a two-hour walk away (or a blink-and-you’ll-miss-it 15 minutes by car). Admire the spooky ruins of the Abbey, which inspired Bram Stoker’s Dracula. Climb the 199 steps that lead to St Mary’s Church, which Stoker also enjoyed for its resident bats; he picked the name for Dracula’s first victim (“Swales”) from one of the gravestones.

Join the locals in Magpie Café, enjoying round two of fish and chips or moules-frites, seafood chowder, or Pacific oysters grown on the seashore within the Lindisfarne National Nature Reserve. A glass or two of chenin blanc will go down nicely. Later, the choice is yours: brave the Dracula Experience or relax with scenic spa treatments at View of Beauty.

Can you imagine what gin flavoured with local honey, sea kelp or heather plucked from the North York Moors tastes like? Discover for yourself at the proudly sustainable Whitby Distillery, which makes rum and gin starring ingredients from the North Yorkshire coastline. After your tasting, spend the night at the bohemian La Rosa Hotel, whose past guests include Lewis Carroll.

Arthur Conan Doyle didn’t send Sherlock to Whitby, but Sam Siciliano did, in The Further Adventures of Sherlock Holmes. Sherlocks Coffee is housed in a characterful 17th-century building, formerly a butcher’s and a dwelling house for multiple families. These days, it’s a cosy little cafe with just enough eccentricity. To continue the theme, Whitby also has a Sherlock’s Escape Room.

A short drive or an hour’s walk from Whitby, Sandsend is a little fishing village with postcard-worthy charm. Bring your net and bucket for the beach, where prime rock pooling awaits. The beck provides safe boating and paddling for little ones. Sandsend is proud of its food and drink; enjoy pub grub at The Stables or pick up picnic provisions from its farm shop.

Continue along the Cleveland Way, pausing to admire Kettleness Beach, one of the most northern beaches on the Yorkshire Coast. The beach is hard to access (involving a steep, rocky scrabble); instead, stroll along Port Mulgrave, a 13-drive or 90-minute walk away. Look out for the old miners’ cottages and fossilised treasures, including ammonites and dinosaur and reptile remains.

The fishing village of Staithes has a pretty harbour and waves dotted with traditional Coble boats. There’s something creative in those waters, if the wealth of artists’ studios and quirky galleries is anything to go by. Wave a paw/claw at Emma Stothard’s striking Blue Lobster sculpture, and follow the Painted Illusion Trail by trompe l’oeil artist and Staithes resident Paul Czainski.

Fact: cream tea tastes even better by the sea. Finish your day on a sugar high with tea and scones at Dotty’s Tearoom. This retro-tastic café will lend you blankets so you can sit outside and snuggle up with your tea and treats. Back inside, browse the vintage homewares for sale and choose something lovely to take home with you.

Sea Drift is famous for its Coble Cake – made with apples and walnuts, and served warm with a pot of cream – but the coffee is also a certified crowd-pleaser. Begin the day with breakfast at this harbourside café, sitting outside if the weather and waves permit (it’s lovely inside, if not). Take a few extra slices of that cake for the road.

Pick from two nautical-but-nice options. One: take to the local waters with Sean and his beloved boat, All My Sons, in partnership with Yorkshire Coast Nature or Three Sisters Sea Trips. In autumn, you might spot whales moving south along Yorkshire’s coastline, guzzling herring and mackerel. On the “Hook & Cook” experience, Sean will show you how to catch, clean, prepare and barbecue fresh mackerel – then scoff it.

Landlubbers: we’ve got you covered. If you don’t fancy salt spray on your lips and the wind in your hair, spend the morning pootling around The Staithes Museum. This eccentric heritage centre is stuffed with thousands of photographs, paintings, prints and objects. Discover Captain Cook’s connection to Staithes: as a young man, he apprenticed as a shop-assistant here, pining for adventures on the seven seas.

Unleash your own inner explorer/pirate on Skinningrove Beach, aka Cattersty Sands, a 15-minute drive away. Turn your gaze to the horizon, looking for ships or whales lobtailing in season. Don’t miss the restored coble boat and its “fishermen”, created by chainsaw sculptor Steve Iredale and fellow sculptor Richard Baker. Nearby, Moss Seat is great for birdwatching; the Hummersea Nature Reserve promises prime walks.

Today’s final destination is Saltburn-by-the-Sea. Old Saltburn was a little hamlet, popular with smugglers; in the Victorian times, Henry Pease had a prophetic vision for Saltburn’s development, stumping up the family finances to bring this vision to life. The town’s seafront “Jewel" streets – Coral, Garnet, Ruby, Emerald, Pearl, Diamond and Amber – are said to result from Henry’s vision. Bed down in the pampering Spa Hotel.

After a “full Yorkshire breakfast” at the hotel, begin the day on a high, taking a ride in Britain’s oldest operating water-balanced cliff lift – a funicular powered by water – which connects the town and beach. Explore the Victorian spa town, admiring its pier and Valley Gardens. Look out for unexpected woolly treasure: knitted creations by the “Yarn Bombers” can magically blossom in the town overnight.

Before leaving the coast behind, have a leisurely rummage in Saltburn’s stylish boutiques. Pick up covetable homewares and gifts from the likes of Lillian Daph, Polyester and Brambles. Edible treasures are guaranteed at Real Meals. Once you’ve shopped to your heart’s content, hop in your car for Pickering, an hour’s drive inland. It’s time to discover the Cleveland Way’s green and leafy side.

No trip along the Cleveland Way is complete without a journey on the North Yorkshire Moors Railway. To complete the last leg of your adventure, hop on a classic steam train to Helmsley, enjoying the scenic views and the retro comfort of your carriage (accessible for wheelchair-users, too). Admire the heather-clad hills and woodland as the train chugs you through the countryside.

You might be reluctant to step off your vintage chariot, but Helmsley Walled Garden has plenty of botanical rewards in store. This horticultural charmer is set amid five pristine acres, revealing floral displays to brighten up your Insta feed: a Physic Garden, Kitchen Garden, Cottage Garden, Clematis Garden, and double herbaceous borders, immortalised in the 2020 film The Secret Garden.

Debrief on your favourite floral moments at the award-winning Vine House Café, within the Walled Gardens. Enjoy tea and cake or something savoury: feta and green bean frittata, or a salad featuring home-grown greens, perhaps? Take the train back to Pickering, where your car awaits, or return using two legs: the four-hour hike is one of the loveliest walks in North Yorkshire.