Helmsley
Trail Running Calendar near Helmsley 2026-2027
Explore the top trail runs near Helmsley for 2026-2027! We've gathered 70 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 10 km trail race inside the enclosed Kiplin Hall estate near Richmond, with a marked route through gardens, woodland, grassland and lakeside paths.
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.
A regency-themed trail event at Castle Howard offering 5k and 10k run or walk options with live string quartet, camping, and dog-friendly waves.
Trail event in Knaresborough offering 10k, half marathon, 20 mile, marathon and ultra with laps on a 6.5 mile course, feed stations and finisher medal.
A 9 km FRA BS fell race with 250 m climb at Sutton Bank Visitor Centre, the second counter in the Dave Parry / Lets Run Winter Fell Race Series, navigation required.
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 races at Aske estate offering 5 km and 10 km routes with marked obstacles and options for owners to run with their dogs.
Night trail race at Sutton Bank Visitor Centre on 31 October 2026 over 7 miles with a marked route, mandatory kit requirements and a three hour time limit.
November 2026
37th Kilburn Kanter is a 24 mile challenge walk with 3,500 ft of ascent across the Hambleton Hills on 7 November 2026, featuring checkpoints and a 10 hour limit.
A 24 hour trail event near Yarm where runners complete a 6.7 km lap each hour for up to 24 hours, limited to 100 places and raising funds for Everymancan.
A 20 km fell race near Pickering in the North York Moors on 15 November 2026, held from Levisham Village Hall with 500 m of climb. Day entry is available with modest fees and teams are allowed.
Charity 5 kilometre trail run at Cowpen Bewley Woodland Park raising funds for Zoe's Place and NeoAngels on a two lap undulating course.
Trail marathon, half marathon and 10 km through Dalby Forest near the North York Moors, chip-timed and canicross friendly with parking available.
December 2026
A 20 km fell race on Gisborough Moors in the North York Moors on Sun 6 Dec 2026, with 850 m of climb. Entry is available by pre-entry and on the day; teams are allowed and the race forms part of the North East Fell Running Champs.
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..
A single-lap, undulating multi-terrain 10 km in Ripon on 28 December 2026, running through woods and Studley parkland with charity support and on-site refreshments.