Virtual Cleveland Way Challenge
Combine moor and sea from your own training routes. The Cleveland Way runs roughly 168 km (about 104 miles) from the market town of Helmsley in the heart of the North York Moors south to Filey Brigg on the North Sea coast, crossing open moorland before swinging south along the clifftops. Route Rally turns every synced walk, run or ride into progress along this horseshoe-shaped trail.
- Route: Cleveland Way
- Distance: 167.7 km
- Elevation gain: 4500 m
- Moors and clifftop horseshoe
- Best for: Medium rallies of your own for walkers and runners, and focused four-to-eight week goals
Planning your challenge
A runner averaging 40 km/week finishes in around four weeks; a walker at 30 km/week takes about five to six weeks, and a cyclist at 150 km/week completes it in about a week.
This is a Medium route by Route Rally distance bands, a manageable goal for a focused month of consistent movement.
Works well for walkers and runners who want a route that combines two distinct landscapes in a single trail.
Create your own rally for your own Cleveland Way target, solo or with a group sharing one leaderboard.
Why this route
- The Cleveland Way covers about 168 km (104 miles) from Helmsley through the North York Moors and along the clifftops to Filey Brigg.
- As a virtual challenge you cover the distance in your own time, with walks, runs and rides from anywhere all counting towards the clifftop finish.
- The horseshoe shape means the route offers two completely different landscapes: open moorland in the west and dramatic sea-cliff scenery in the east.
- Its medium length makes it achievable in a focused month at a comfortable walking or running pace.
- The combination of moorland and coast gives it real variety and a strong visual identity even as a virtual target.
Highlights
- Start at Helmsley, a market town on the edge of the North York Moors
- Cross open moorland above Whitby, Roseberry Topping and the Hambleton Hills
- Reach the North Sea coast at Saltburn and follow the clifftops south
- Finish at Filey Brigg, a rocky headland on the Yorkshire coast
Common questions
How do my walks count towards the moors and the coast?
You log nothing twice. A walk, a run or a ride arrives from your tracker and carries you round the horseshoe from Helmsley. A runner at 40 km a week finishes in about four weeks, and a walker at 30 km a week in five to six.
Do I have to be in North Yorkshire?
No. What you are covering is the trail's length, not its ground, so your local paths and pavements will get you across it. The real trail changes character halfway, from open moorland to sea cliffs; on your own routes that change of scene is up to you, but the 168 km is the same.
How long does it take?
At 30 km a week it takes around five to six weeks. Runners at 40 km a week finish in about four weeks, and at 50 km a week you can complete it in under a month. You decide the finishing date as you set the rally up.
Does the Cleveland Way end at the same place as the Yorkshire Wolds Way?
Both finish near Filey on the Yorkshire coast, which is a popular meeting point for walkers who want to link the two trails. As virtual challenges they are separate routes with separate leaderboards.
Start your Cleveland Way Conquest
Joining is free. Connect Strava or Apple Health once and every ride, run or walk you record syncs automatically, moving you along the route without anything else to log.