Trail Running calendar near Pickering 2026-2027

Take on the Totley Two Turtle Doves fell race in the Peak District this Boxing Day, a bracing 4.8 mile course with 820 ft of climb. Winter kit is required and Totley AC Pavilion provides toilets, showers and changing rooms.

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..

Join The Drop UK in Skipton for a daring navigation challenge: blindfolded and dropped at an undisclosed location you must find your way back without maps or devices. Choose 6, 10 or 15 mile options and hand in electronics at registration.

Bracing winter fell race around Bilberry Fields in Todmorden, offering scenic South West Pennine views and a testing 4.6 mile route with plenty of climb. Friendly club atmosphere with cheap pre entry and on the day entry available.

Celebrate New Year's Eve with the Wormstones fell race in the Peak District, an energetic 8 km with about 400 m of climb. Join at The Beehive in Glossop on 31 Dec 2026 for tough trails, great company and curry after the run.

Ring in the New Year with this scenic, hilly 10.8 km trail around Penistone Hill Country Park near Haworth on 31 December 2026. Entries are limited, chip timing is new for 2026, and every finisher receives a bottle of Daleside beer plus cof..

An 18 mile circular trail from Robin Hoods Bay on 9 January 2027, following the Cinder Track and Cleveland Way. Entry is limited to 150 runners and £1 from each entry supports the Cleveland Way National Trail.

A circular roughly 30 miles coastal race from Robin Hood's Bay through Ravenscar and Scalby Mills following the Cleveland Way and the Cinder Track. Entry is limited to 200 runners and the minimum age is 18.

A winter, waymarked trail challenge on the Pendle Way offering about 45 miles or an alternative 30 miles route for runners and walkers, with significant ascent and required winter kit and navigation skills.

Explore the Yorkshire Dales on a guided weekend taking on the 24 mile Yorkshire Three Peaks route with bunkhouse nights in Horton in Ribblesdale. Enjoy a relaxed 10 km loop on Sunday plus coaching, a training plan and event photos.