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.
July 2027
A circular ~120 mile ultra across the North York Moors that visits the ten highest hills and ancient sites, with indoor checkpoints, mandatory kit requirements and a 35 hour limit.
A fully tracked 36 mile ultra along the Esk Valley Way from Castleton to Whitby Harbour with checkpoints, train access and no cut off time.
August 2027
Farndale trail races from Hutton Le Hole offer three unmarked routes with mandatory kit, downloadable maps and capped entries; parking and basic campervan facilities are available.
Trail half marathon in the North York Moors featuring Roseberry Topping, about 13.1 miles, limited to 50 places with a five hour cut off and a bespoke finisher medal.
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.
Trail races at Guisborough on 29 August 2027 offering three distances with published ascent figures, mandatory kit and self-navigation using downloadable maps.
September 2027
Inflatable 5K in York on 18 September 2027 offers 2.5k to 15k inflatable obstacle laps, music zones, medals and on-course water for all participants.
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.
November 2027
Trail festival in Knaresborough with 10k (ish), half, 20-mile and marathon options on a 6.5-mile loop, with feed stations, marshals, and nearby parking.