Cleveland Way: 9-day itinerary

Begins gently through the Rye Valley's woodland and farmland to Rievaulx Abbey, then climbs onto the limestone edge of the Hambleton Hills at Sutton Bank — one long, sudden view west across the Vale of York. The ancient Hambleton drove road gives easy, well-graded walking on to Osmotherley, the last proper village before the high moors. Repeated small climbs rather than one big one; well within a day for most walkers, and the last stretch of comfortable underfoot walking before the moorland roller-coaster that follows.

Logistics: Sutton Bank has a visitor centre, café and bus service — a natural resupply roughly a third of the way through.

Navigation: Easy to follow throughout on well-used paths and the old drove road; little difficulty.

The hardest stretch on the whole trail per kilometre: five separate moorland tops — Carlton Bank, Cringle Moor, Cold Moor, Hasty Bank and Urra Moor — each climbed and dropped in close succession, with almost no flat ground between them. Round Hill, on Urra Moor, is the highest point in the North York Moors. Big views on a clear day, but relentless underfoot, with only a single café the whole way. The old ironstone railway trackbed finally flattens things out toward the end, easing the descent into Kildale.

Logistics: Only one place to buy food on this whole stretch (Lord Stones café near Carlton Bank) — carry supplies for the rest of the day.

Navigation: Stone markers and cairns on the tops are adequate in clear weather; in mist the repeated up-and-down makes it easy to lose track of which summit you're on.

Climbs straight out of tiny Kildale to Captain Cook's Monument on Easby Moor, with Roseberry Topping's sharp, quarried peak visible off to the north — locally nicknamed the Yorkshire Matterhorn, though the trail doesn't go over it. Beyond Great Ayton Moor and Highcliff Nab the route drops into Guisborough Woods, the longest stretch of forestry on the whole Cleveland Way, sheltered and quiet after two moorland sections. Genuinely nothing open anywhere on this stretch — no shop, café or pub — so it needs planning around rather than relying on.

Logistics: Nothing is open on this whole stretch — carry all food and water; Kildale itself has no shop either.

Navigation: Clear paths throughout; the forestry tracks in Guisborough Woods are the only place multiple paths cross, so waymarks need following carefully there.

The hinge of the whole trail: quiet former ironstone country around Slapewath gives way abruptly to Saltburn-by-the-Sea, a proper Victorian seaside town with a working cliff lift, and the moment the Cleveland Way stops being a moorland walk and becomes a coast walk for the rest of its length. From Saltburn the trail joins the cliff path south to Skinningrove, a working ironworks village tucked into a steep valley — the first of the small, tightly packed communities that define the coastal half.

Logistics: Saltburn is the best resupply point on the whole trail — full shops, a station, and the last easy town until Whitby.

Navigation: Well waymarked and busy with local walkers around Saltburn; easy underfoot.

The classic stretch of the coastal half: constant climbing and dropping into and out of a run of fishing villages — Staithes, Runswick Bay, Sandsend — each a steep descent to sea level and an equally steep climb back out. Boulby Cliff, just past Skinningrove, is the highest point on England's east coast at 203m. Whitby, roughly two-thirds through, is the one proper town and a natural overnight break. Beyond it, Robin Hood's Bay and then a long climb onto Ravenscar's old alum-works plateau finish a long, tiring, spectacular stretch — most walkers split it over more than one day.

Logistics: This is a long section to do in one push — most walkers split it, commonly at Whitby or Robin Hood's Bay, both with full services.

Navigation: Well waymarked and heavily used throughout; the only real hazard is underestimating how much climbing the repeated village descents add up to.

Leaves Ravenscar's old alum-works plateau for a gentler, more wooded stretch — Hayburn Wyke's wooded bay and waterfall is the highlight, a sudden contrast to the open cliffs before and after it. Easier underfoot than the previous section, with fewer sharp village descents, before the trail builds through Scalby and Scarborough's northern suburbs into a proper large town. Scarborough itself, with its castle headland splitting North and South Bay, is by far the biggest settlement on the whole trail.

Navigation: Well waymarked; the approach into Scarborough is on urban paths and promenade, easy to follow but a change of character from the cliffs.

Short but the most repetitively broken-up walking on the trail — a string of small becks and bays, Cayton Bay among them, each cutting a little climb and drop into the cliff line. The route has been permanently diverted inland near Knipe Point after the original path was lost to erosion, briefly following the A165 before returning to the coast. Ends at Filey Brigg, a long rock spit reaching out to sea and a genuinely different, calmer finish than the cliffs that came before — and the start of the Yorkshire Wolds Way for anyone continuing.

Logistics: The clifftop path near Knipe Point has been lost to erosion and is diverted onto the A165 for a short stretch — a permanent rerouting, not a temporary closure.

Navigation: Well waymarked; the erosion diversion is signed but the line shifts over time, so follow current waymarks rather than an old map here.