Cleveland Hills
Trail Running Calendar near Cleveland Hills 2026-2027
Explore the top trail runs near Cleveland Hills for 2026-2027! We've gathered 68 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
MapRun navigation score event in Guisborough Forest on 22 May 2027, pre entry required with fees from £7, minimum age 14 and FRA permit and insurance in place.
A 36 hour single stage trail ultramarathon along the Cleveland Way roughly 110 miles long with 5000 m ascent, compulsory tracker, checkpoints and mandatory kit requirements.
An 80 km point to point ultra across the North Yorkshire moors from Ingleby Arncliffe to Robin Hoods Bay with three staffed checkpoints and ITRA points.
June 2027
Trail event at Guisborough Rugby Club offering 40 km and 60 km options, solo or relay, raising funds for Teesside Samaritans with checkpoints and medical cover.
Race for Life Darlington at South Park on 6 June 2027 offers 3k and 5k routes across grass and park paths to raise funds for Cancer Research UK.
An overnight circular trail run of about 40 miles across the North York Moors starting and finishing in Goathland with a lamplighter ceremony at the village hall.
Night trail run of about 20 miles on a circular route across the North York Moors, starting and finishing in Goathland with the start marked by a lamplighter.
Supported coastal and moorland trail challenge from Scarborough to Whitby and back with GPS tracking, covered rest stops and multiple distances including 100 km and 50 km.
July 2027
A point to point trail challenge of just over 40 miles along the classic Lyke Wake route with handicap starts, seven checkpoints, mandatory kit checks and charitable donations.
A 50K trail ultra from Pickering to Whitby passing eight railway stations, on mixed terrain alongside a heritage railway, with five marshaled checkpoints and a 13 hour limit.
Looped trail event in Masham with 3 hour and 6 hour options on about 3.3 to 3.5 mile laps, featuring feed stations, marshals, a medal, beer and a sausage sandwich.
A circular 120 mile ultra across the North York Moors visiting the ten highest hills, with 16,000 ft of ascent, indoor checkpoints, mandatory kit and a 35 hour limit.
A 10 km fell race at Ravenscar in the North York Moors with 250 m of climb, on-the-day entry and team scoring, organised by Scarborough AC.
A fully tracked 36 mile ultra along the Esk Valley Way from Castleton to Whitby Harbour with five staffed checkpoints, GPS tracking and village return options.
August 2027
Trail races at Hutton Le Hole offering 29 miles, 16.5 miles and 8.3 miles routes with mandatory kit, route navigation, time limits and limited entries.
A trail half marathon in the North York Moors featuring forest tracks, heather moorland and ascents of Roseberry Topping, limited to 50 runners with a 5 hour cut off.
An 11.2 km fell race in Langdale End, Scarborough with 475 m ascent, BM category and UK Athletics permit; entry on the day with modest fees.
Short fell race to Roseberry Topping in the North York Moors, 2.3 km with 217 m climb, entry on the day and junior races included.