Helmsley
Trail Running Calendar near Helmsley 2026-2027
Explore the top trail runs near Helmsley for 2026-2027! We've gathered 74 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
February 2027
A winter trail race at Saltburn offering three mapped distances from 7.5 to 28 miles, mandatory safety kit and time limits for each course. Entries are limited and prizes are awarded across age categories.
Experience a friendly trail half marathon through the scenic Yorkshire Wolds. Enjoy a well marked circular route with a generous five hour cut off and a unique wildflower seed medal at the finish.
A trail half marathon in the North York Moors starting and finishing at Levisham Village Hall, featuring the Hole of Horcum, two checkpoints and a bespoke finisher medal.
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 ultramarathon from Guisborough to Helmsley across the North York Moors with 2300 m ascent, checkpoint cutoffs and a 16 hour time limit.
April 2027
A trail run and walk at Guisborough Rugby Club on Saturday 3 April 2027 supporting Teesside Samaritans. Options include a 10 km walk or run and a half marathon on the official Samaritans Way, with profits donated to the charity.
A circular trail run near the Yorkshire Cycle Hub of about 10 km with 1100 ft ascent that raises funds for mental health; limited to 100 entries and dogs are welcome.
An 80 km ultra along Wainwright’s coast to coast route across the North York Moors with mandatory kit checks, GPX navigation and staffed aid stations offering food, drink and medical 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 10 km along the Cleveland Way from Skinningrove to the Charm Bracelet sculpture and back, with 890 ft ascent, a marshaled checkpoint in Saltburn, and entries for ages over 15.
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.
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 muddy 5k obstacle course at The Knavesmire in York featuring climbs, crawls and slides. Waves start every 15 minutes and participants must be 13 or older. On-site parking, refreshments and a minimum fundraising target are part of the event.
Hardmoors White Horse at Sutton Bank on 9 May 2027 offers three trail distances with published ascent and time limits. Competitors must carry mandatory kit, navigate with supplied maps and GPX files, and use their own cup at checkpoints.
A trail race from Studley Roger near Ripon following the Ripon Rowel with routes of 14.2, 23 and 35.1 miles visiting Fountains Abbey and valley woods.
A circa 13.2 mile trail half marathon around Black Hambleton and Silton Woods near Osmotherley with marked navigation, one checkpoint, a four hour limit and a 50 runner cap.
Point to point 30 km trail across the North York Moors on the Wainwright Coast to Coast path, with a checkpoint at Lordstones and a six hour cut off.