How Many Days Do You Need for the Cleveland Way?

The question I get asked most about the Cleveland Way is how long it takes, and the honest answer is a little longer than the mileage suggests. It is 109 miles from Helmsley to Filey, and most people give it eight or nine days.

The short answer: eight or nine days

Nine days works out at around twelve miles a day. Eight days pushes you closer to fourteen. On paper that is a gentle amount of walking. On the ground it depends entirely on which bit of the path you happen to be standing on.

The first half is moorland. From Helmsley the route climbs to Sutton Bank, then out across the tops to Osmotherley, where there is heather to every horizon and very little between you and the weather. The stretch past Clay Bank and the Wainstones is a switchback along the western edge, and it will take more out of your legs than the map admits. The second half is coast, from Saltburn-by-the-Sea round to Filey, and the cliffs go up and down rather more than a sea view implies.

My advice, for what it is worth from a man who likes a long lunch: take the nine days. The extra day costs you one more night's bed and buys you the time to sit down at Sutton Bank, which James Herriot called the finest view in England, with the White Horse gleaming below. Rushing past that would be a waste of a good pair of boots.

What the stages look like

These are the natural stopping points, and they space out sensibly:

• Helmsley — a market town start, with the ruins of Rievaulx Abbey about an hour in.
• Sutton Bank — the view, and the beginning of the escarpment.
• Osmotherley — the moors proper begin here.
• Clay Bank (Great Broughton) — the Wainstones and the hardest ups and downs of the inland half.
• Saltburn-by-the-Sea — where the path meets the coast, at a Victorian resort with a cliff tramway.
• Whitby — abbey, harbour, Dracula, and the best fish and chips on the route.
• Robin Hood's Bay — red roofs stacked down to the slipway, the classic smugglers' village.
• Scarborough — two bays and a headland castle.
• Filey — the finish on Filey Brigg, with the whole coast behind you.

Walk it in that order, Helmsley to Filey, and you get the hard moorland while your legs are fresh and the seaside towns when they are not. There is also something to be said for finishing within sight of a bench and a pot of tea rather than a heather moor.

Where to stay along the route

Beds on the inland half are thinner on the ground than on the coast, so book those first. Near the Helmsley end, The Old Back Kitchen at Bonfield Ghyll Farm is a cottage rather than a bunk, which suits anyone wanting a proper night before the walking starts. If you would rather have a hotel bed and a bar to sit in for a night off the path, The Northallerton Inn is worth a look.

Campers have options at either end. Raven Gill Campsite is near a train station, which matters more than it sounds when your plans change at four in the afternoon. Crief Lodges and Oak Cottage cover the middle ground between canvas and comfort. On the coast, Redcar Beach Caravan Park has EV charging nearby and a station within reach — handy if someone is driving out to meet you.

If you haven't got nine days

Then take the coast. Saltburn to Filey by way of Whitby, Robin Hood's Bay and Scarborough gives you four days of cliff path, four proper towns and a finish worth photographing. You are never far from a town with a kitchen and a room on that half, so a short day costs you nothing much, which is more than can be said for the moors.

The other sensible approach is to split the route in two and come back. Do the inland half in spring, when the light on the escarpment is at its best, and save the coast for late summer. Nobody hands out medals for doing it in one go. If you are driving between sections rather than walking them, the road trip routes will fill in the gaps nicely.