The Cleveland Way: York and Whitby

This six-day Cleveland Way National Trail break visits the ancient city of York, the haunted town of Whitby and the dramatic North York Moors. You’ll hike ‘The Yorkshire Matterhorn’, travel by train across England’s finest National Park, explore the famous Whitby Abbey and eat fish & chips by the sea.

Walking the entire 175km/109-mile length of the Cleveland Way is a challenge. For adventurous hikers, it’s a long journey on rugged coastal and moorland trails that requires nine days of walking. So we’ve put together a condensed six-day itinerary that explores some of the main highlights. It covers a total of 35km/22 miles on foot and visits some of the most historic and spectacular locations on the Cleveland Way National Trail route. The trip starts with two days in York, where you’ll take a spooky ghost tour, walk the ancient city walls, visit the Jorvik Viking Centre and marvel at York Minster. From York you’ll travel on a scenic bus route across the North York Moors to the seaside town of Whitby, famous for its beautiful harbour and as the birthplace of Dracula. The final three days explore some of Britain’s best coastal walks around the fishing village of Robin Hood’s Bay, the iconic peak of Roseberry Topping, and the sweeping sands of Runswick Bay.

Tour Overview

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History / Coastal

Landscape Type

By Water / Hills and moorland

The Cleveland Way: York and Whitby

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This itinerary breaks down the six-day trip into daily sections. The first three days are spent exploring the city of York and the town of Whitby, and the final three days involve more challenging walks on hilly and coastal trails totalling 35km/22 miles of hiking.

Arrive in the historic city of York, the birthplace of Guy Fawkes and one of the finest heritage cities in England. You’ll have plenty of time to stroll around the city and enjoy an early-evening meal in one of the many traditional pubs, bars, cafes or restaurants. Then take part in a ghost tour in one of Britain’s most haunted cities.

With its Roman roots and Viking past, York is a city packed with history, offering endless options for visitors to explore. Begin the day with a walk around the ancient city walls, then uncover the city’s Roman foundations at the Yorkshire Museum. The famous Jorvik Centre brings alive the sounds and smells of York’s Viking age, majestic York Minster is northern Europe’s largest medieval cathedral, and the narrow-cobbled street of the Shambles is full of fascinating shops, cafes and restaurants.

The day starts with a 10.23am ride on board the Coastliner bus to Whitby, where you can look out for the distinctive landscape of the Hole of Horcum and take in the first glimpse of the stunning sea views on the most scenic bus ride in Britain.  You’ll arrive in Whitby at lunchtime, giving you an afternoon to explore its traditional streets and shops. You can take boat trips in the harbour, go rock-pooling on the beach at low tide, visit the Whitby Museum or Captain Cook Museum, and climb the famous 199 steps  to Whitby Abbey.

Catch an early bus to Robin Hood’s Bay (11km/7 miles south of Whitby) and get off 1km early at St Stephen’s Old Church to admire its striking interior. Head down steep streets into the smugglers’ bolthole of Robin Hood’s Bay, full of hidden passageways, fishermen’s cottages and stone chapels. Hunt for fossils on the beach, then follow the Cleveland Way north to Whitby, taking in stunning cliff-top scenery, the historic ruins of Whitby Abbey and the 199 stone steps leading back to the heart of Whitby. 13km/8 miles

Start with an 8.45am train journey across the North York Moors National Park to the village of Great Ayton, where legendary explorer Captain Cook grew up. From here you’ll begin a circular walk up Roseberry Topping, known locally as ‘The Yorkshire Matterhorn’. Despite its dramatic appearance Roseberry Topping is only 320 metres high and this delightful walk explores the countryside around it, including oak woodlands, heather moorland and Captain Cook’s Monument on Easby Moor. 11.7km/7.3 miles

Catch the bus to Runswick Bay, then enjoy a 13km/8-mile walk back to Whitby along the Cleveland Way. Check the tide times before walking south along Runswick Bay beach. This is one of England’s best spots for beachcombing, so when the tide is out hunt for shells, seaweed, fossils and rare nuggets of jet in the sand. Climb steeply out of the bay at Hob Holes, then walk along soaring cliffs that offer some of the finest coastal walking in Yorkshire. Stop for tea, coffee and cake at Sandsend, then (if the tide is out) stroll back to Whitby along three glorious miles of beach. 12km/7.5 miles


York and Whitby have plenty of accommodation options, ranging from hotels and B&Bs to self-catering cottages and traditional pubs. The Visit York website is a good place to start looking for days one and two, while the Discover Yorkshire Coast website has plenty of great suggestions around Whitby.


Leeds Bradford is the closest airport, where the 757 bus runs to Leeds train station, which has a regular rail service to York. From Manchester Airport, TransPennine Express trains run to York around the clock

Hull is the nearest port for European ferry services, just a one-hour drive from York.

Located just 20 minutes from the M1/M62 motorway network, York is an easy city to reach by car, with six Park & Ride sites making parking and travelling into the city easier.

York is easily accessible by train in around two hours from London, Edinburgh and Manchester.


With a busy city and one of Yorkshire’s biggest coastal towns as a base, accommodation is readily available but York and Whitby are both popular with tourists all-year round so book early to avoid gaps in your itinerary.

The coastal walks and the ascent of Roseberry Topping can be done at any time of year but be warned: it gets very cold on the Yorkshire coast in the winter months! Spring is the best time to visit, with warmer temperatures and the sea cliffs are alive with thousands of nesting seabirds. This itinerary is comfortably within the capabilities of all experienced walkers with good levels of fitness.

Food & Drink

York and Whitby are perfect for lovers of good food and beer. Fish and chips is a must on one of your trips to the coast and the street food scene at the Shambles Market and Food Court in York is excellent. Whitby is full of good pubs and restaurants serving everything from seafood and stews to pie and mash, plus the popular Botham’s of Whitby on Skinner Street that manages to combine French-style patisserie and traditional Yorkshire bakery! Beer is a big deal in these parts too, with a bewilderingly large range of local ales. Try the great local beers from Whitby Brewery from their Taproom right by the Cleveland Way.

Maps, Guidebooks and Merchandise

The official guidebook and map for the Trail are available from the National Trails Shop along with a wide range of gifts and other merchandise.

Itinerary Map

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