Guisborough
Trail Running Calendar near Guisborough 2026-2027
Explore the top trail runs near Guisborough for 2026-2027! We've gathered 68 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 5 km trail run at HMP Kirklevington Grange on 3 September 2026 with a minimum age of 12, on-course cake, parking and race plus series prizes.
A 10 mile trail run on the North York Moors following part of the Lykewake Walk, visiting Lilla Cross and Louven Howe with a three hour time limit and required safety kit.
A coastal ultramarathon along the Cleveland Way from Guisborough to Filey covering about 62 miles with checkpoints, mandatory kit and an 18 hour time limit.
Tackle the Fryup Frazzler in the North York Moors, a scenic 5.8 mile fell run from the Cycle Hub cafe with roughly 475 m of climb. Part of the Esk Valley summer fell series, it mixes tough slopes with rewarding views.
A flexible 7 hour time challenge at Herrington Country Park on 20 September 2026 with distances from 3 km to 50 km and a rubber duck themed medal for finishers.
Trail runs at Locomotion, Eaglescliffe with 10- and 5-mile routes partly on the original Stockton and Darlington Railway, raising funds for Great North Air Ambulance and MND.
A 10 mile multi terrain event at Catterick Garrison on 26 September 2026, offering a standard run, a 35lb bergen TAB option and a canicross category.
October 2026
An evening 10k trail race inside the enclosed Kiplin Hall estate near Richmond, featuring gardens, woodland and lakeside paths, marked route and limited parking.
A 7 hour Time Challenge on the River Wear in Durham with distances from 3 km to ultra, Scare Bear themed medals and distance pins, signed trail laps and aid tables offering drinks and snacks including vegan options.
Tackle the Viking Chase, a 12 km fell race across the North York Moors on 11 Oct 2026, featuring 572 m of climb and sweeping moorland views. Entry on the day, adults only, with proceeds to Cleveland Mountain Rescue.
Regency themed 5km trail at Castle Howard on 11 October 2026 for runners and their dogs, featuring a live string quartet, a mass regency dance, camping and timed results.
A 9 km fell race at Sutton Bank with 250 m of climb, navigational sections and mandatory FRA kit as part of the winter fell race series.
Tackle Lockton Limping, a scenic fell race across the North York Moors covering 11.2 km with 350 m of climb and sweeping views. Entry is on the day at Lockton Village Hall, perfect for both competitive and social runners.
Obstacle course event for dogs and owners at Aske estate near Richmond, North Yorkshire, offering 5 km and 10 km courses with dozens of marked obstacles.
A 5 km Halloween trail at Trimdon on 29 October 2026 featuring a haunted woods course, costumes, participant soup and prizes, age limit 12 plus, entry fees from £10.
Night trail race at Sutton Bank Visitor Centre covering 7 miles with 344 m ascent, a 150 runner limit and a three hour time limit.
November 2026