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.
May 2027
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.
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.
A 10 km beach race in Filey, North Yorkshire, organised by Filey Lions Club to raise funds for local charities.
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 53 miles coastal trail race from Fraisthorpe to Whitby via the King Charles Way and Cleveland Way with an 18 hour time limit and mandatory kit checks.
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.
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.
Trail Marathon, Half Marathon and 10k at Guisborough Rugby Club on 29 August 2027 with mandatory kit, downloadable maps, limited parking and fixed entry limits.