Helmsley
Trail Running Calendar near Helmsley 2026-2027
Explore the top trail runs near Helmsley for 2026-2027! We've gathered 70 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
January 2027
Winter trail event on Saturday 9 January 2027 around Robin Hoods Bay covering 17.5 miles with 1700 ft ascent and an eight hour time limit.
A 31 mile winter trail race from Robin Hood's Bay to Scarborough along the Cleveland Way and Cinder Track, with 3400 ft ascent and an 11 hour time limit.
A 5 mile night trail race in Dalby Forest on mostly unused single track paths, with a 16 plus age limit and a £19 entry fee.
A winter 50K on the North York Moors featuring two waterfalls, castle ruins, ancient woodland and coastal views, with four checkpoints and a tracked, waymarked route.
February 2027
Trail marathon plus half and 10k at Saltburn by the Sea on 7 February 2027 with compulsory kit, downloadable maps and a 330 runner limit.
Circular trail half marathon in the Yorkshire Wolds near Tibthorpe: 14 miles, 1,200 ft climb, 5 hour cut off and a plantable wildflower medal.
A trail half marathon in the North York Moors, starting and finishing at Levisham Village Hall, passing through the Hole of Horcum; 50 places and a 5 hour limit.
Trail runs at Fountains Abbey on 28 February 2027 feature 5 km, 10 km and half marathon routes through the Deer Park and Water Garden with live chip timing.
March 2027
A 53 mile point to point ultramarathon across the North York Moors and Cleveland Hills from Guisborough to Helmsley with mandatory kit and a 16 hour limit.
Blubberhouses Moor is a 23 plus mile walkers and runners event around Bland Hill and local reservoirs, limited to 250 entrants, with checkpoints and a finish meal.
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 self-sufficient ultra along Wainwright’s coast to coast route across the North York Moors with staffed aid stations, mandatory kit checks and GPX navigation support.
Trail runs at Bramham Park on 4 April 2027 with 5 km, 10 km and a half marathon across the estate; canicross friendly and parking available.
Trail event named Charm Bracelet 10K follows the Cleveland Way between Skinningrove and Saltburn over a 7.4 mile route with 890 ft of elevation.
A 14.35 mile coastal trail from Redcar to Staithes with 1591 ft of climbing, two marshalled aid stations, a finishers medal, and a five hour completion window.
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.
A self navigated trail challenge from Goathland in the North York Moors, about 37 miles visiting five triangulation pillars, open to solo entrants or pairs with a 15 hour limit.