Whitby
Trail Running Calendar near Whitby 2026-2027
Explore the top trail runs near Whitby for 2026-2027! We've gathered 46 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
March 2027
A 53 miles ultramarathon from Guisborough to Helmsley across the North York Moors with 2,300 m ascent, mandatory kit and a 16 hour limit.
April 2027
Trail run and walk at Guisborough Rugby Club on 3 April 2027 with 10 km and half marathon options, raising funds for Teesside Samaritans and donating event profits.
An 80 km ultra along Wainwright’s coast to coast from Ingleby Cross to Robin Hood’s Bay with mandatory kit checks, staffed aid stations and GPX route files.
Trail out and back along the Cleveland Way from Skinningrove to Saltburn, about 7.4 miles with 890 ft elevation, open to runners and walkers aged 15 and over.
A 14.35 mile coastal trail from Redcar to Staithes with cliffs, sand and 1591 ft ascent, two aid stations, a finishers medal and a five hour time limit.
A coastal trail marathon from Redcar to Whitby following the England Coast Path and Cleveland Way. The 26.57 mile route includes sand, cliffs and 3,263 ft of ascent, with four aid stations, marshaled checkpoints and a GPX route available.
Circa 37 mile navigational challenge around Goathland visiting five triangulation pillars, open to solo entrants or pairs, self supported with three checkpoints and a 15 hour limit.
May 2027
A fully tracked 36 mile trail ultramarathon around the Esk Valley Walk, starting and finishing in Glaisdale. The route has about 4487 ft of ascent, five marshaled checkpoints, a 14 hour cut-off, and options for a finisher medal and t-shirt or tree pl..
A circa 13.2 mile trail half marathon around Black Hambleton and Silton Woods with varied terrain, a 4 hour limit, limited entries and mandatory safety kit.
Point to point 80 km ultra across the North Yorkshire moors from Ingleby Arncliffe to Robin Hood's Bay with three staffed checkpoints and a 15 hour cut off.
June 2027
A 160 mile single stage ultra from Scalby to Filey via the Tabular Hills and Cleveland Way, with 6700 m ascent, a 50 hour limit and mandatory vehicle support.
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.
A 110 mile single-stage trail ultramarathon on the Cleveland Way from Helmsley to Filey with 5,000 m ascent and a 36 hour time limit.
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.
A 20 miles night trail from Goathland Village Hall across the North York Moors, run from sunset to sunrise with checkpoints, trackers and a finisher medal.
Explore the North Yorkshire coast and moors on a fully supported trek or trail run with distances ranging from 10 miles to a 100 km loop starting in Scarborough.
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 from Pickering to Whitby that passes eight railway stations, has 3322 ft of ascent, five checkpoints and a 13 hours completion limit; walkers allowed.