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.
March 2027
A 16.4 km fell race in the North York Moors with 825 m of ascent, starting near the Lion Inn by Castleton, Whitby.
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.
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.
A 32 mile route across the Yorkshire Wolds from Driffield Showground to be completed within 12 hours, with checkpoints offering food, basic camping and free parking.
An 80 km self sufficient ultra across the North York Moors following Wainwright’s coast to coast route with staffed aid stations and mandatory kit checks.
A BM-category fell race in the North York Moors covering 11.9 km with 290 m of climb, held in Goathland with registration at the village hall and on-day entry available.
A coastal trail event on the Cleveland Way between Skinningrove and Saltburn, advertised as 10K but mapped at 7.4 miles with 890 ft of ascent, open to runners and walkers over 15.
A 14.35 mile trail from Redcar to Staithes along coastal paths and cliffs, with about 1591 ft of ascent, two marshalled aid stations and a finishers medal.
A coastal trail marathon from Redcar to Whitby covering 26.57 miles and 3263 ft ascent, with varied terrain, four aid stations and a 10 hour completion limit.
A self-navigated circa 37-mile challenge from Goathland visiting five Triangulation Pillars, open to solo entrants or pairs with a 15 hour time limit.
A 52 km circular trail across the Yorkshire Wolds with four indoor checkpoints, live GPS tracking and a 12 hour cut off, based at Field House Camping & Coffee Barn.
A woodland fell race of 10.71 km with 390 m climb around Kilburn Forest, run under Fell Runner Association rules to raise funds for Herriot Hospice Homecare.
May 2027
A fully tracked 36 mile trail ultra along the Esk Valley Walk from Glaisdale with 4,487 ft of ascent, five marshaled checkpoints and a 14 hour completion limit.
A 5k obstacle event at The Knavesmire, York combining grass and trail sections with muddy obstacles; participants must be 13+, minimum fundraising £50.
Trail half marathon of about 13.2 miles around Black Hambleton and Silton Woods near Osmotherley, with mapped route, one checkpoint, mandatory kit list and a 4 hour limit.
An 11 km fell race in the North York Moors on 19 May 2027 with 375 m of climb, Clay Bank venue, day entry only and team scoring available.
A 160 mile single stage ultramarathon from Scalby to Filey via the Tabular Hills and Cleveland Way with 6700 m ascent and a 50 hour limit; motorised support crews required.
MapRun navigation score event in Guisborough Forest on 22 May 2027, pre entry required with fees from £7, minimum age 14 and FRA permit and insurance in place.
A 36 hour single stage trail ultramarathon along the Cleveland Way roughly 110 miles long with 5000 m ascent, compulsory tracker, checkpoints and mandatory kit requirements.