Pickering
Trail Running Calendar near Pickering 2026-2027
Explore the top trail runs near Pickering for 2026-2027! We've gathered 67 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A 20 km fell race in the North York Moors with 500 m ascent, based at Levisham Village Hall on 15 November 2026; day-entry is available and minimum age is 18.
Trail marathon, half marathon and 10km through Dalby Forest on 29 November 2026 with chip timing, canicross friendly rules and subsidised parking.
December 2026
Guisborough Moors is a 12.5 mile 20.1 km fell race on 6 December from Guisborough Sea Cadets Hall with about 792 m ascent and entry on the day.
A festive, multi-terrain race of about 7 miles near Loftus on 20 December 2026 with chip timing, a finisher T-shirt, and limited entries.
Take on a scenic 8.8 km fell race from Guisborough Rugby Club through the North York Moors, with 376 m of climb to test your legs. Junior races and team categories make it a festive late December outing with on the day entries and post race refreshme..
January 2027
An approximately 17.5 mile circular winter trail race from Robin Hoods Bay with three checkpoints, an eight hour limit and compulsory safety kit.
A circular 30 mile trail race from Robin Hood's Bay that follows the Cleveland Way and Cinder Track through Ravenscar, Hayburn Wyke, Crookness and Scalby Mills.
An 8.3 km senior fell race in the North York Moors with 220 m climb, entry on the day and team competition options.
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.
February 2027
Trail marathon, half and 10k at Saltburn-by-the-Sea with self-navigation, mandatory kit requirements and a 330 runner limit.
A 16.5 km fell race in the North York Moors with 573 m ascent, based at Ingleby Cross Village Hall and offering entry on the day under FRA permit.
A 10.4 km fell race in the North York Moors from St Helens church, Saltburn, with 350 m ascent, on the day entry and a 120 runner limit.
A trail half marathon from Levisham Village Hall through the North York Moors and the Hole of Horcum with two checkpoints, a five hour limit and a bespoke finisher medal.
March 2027
Fell race in the North York Moors on 6 March 2027 covering 14.3 km with 470 m of climb; on the day entry is available and proceeds support Cleveland Mountain Rescue Team.
A 55 mile ultramarathon from Guisborough to Helmsley across the North York Moors, requiring mandatory kit, checkpoint checks and a 16 hour completion limit.
A 16.4 km fell race in the North York Moors with 825 m of ascent, starting near the Lion Inn by Castleton, Whitby.
Orienteering based around 24 mile route in the North York Moors with ordered checkpoints, staffed pit stops and required survival kit, supporting Cleveland Mountain Rescue Team.
Multi terrain 10 km around Helmsley on 28 March 2027 with an undulating one lap route, a 430 runner limit, and proceeds supporting local charities.