Trail Running calendar near Pickering 2026-2027

Take on the Cautley Horseshoe fell race near Sedbergh on 6 May 2026, a short but brutal 7.5 km with 805 m of ascent and spectacular upland views. Entry on the day is £5 and the Cross Keys Inn will be open for post race food and drink.

Tackle a spirited 5.4 km village course with 180 m of climb in Lothersdale on 6 May 2026, starting from a carrot on the track for a touch of local charm. Day entries only and small fees make this a relaxed, community friendly hill run.

An evening pop up running event in Kirkstall offering 5k and 10k routes, on-the-day or online entry, food, a jumble medal and a drink for runners. Open to entrants aged 16 and over on 7 May 2026.

A BM-category fell race in Ilkley on 7 May 2026, covering 11.2 km with 335 m of climb. On-the-day entry is available for £5 and the race holds UK Athletics insurance through the FRA.

Take on the classic Pinhaw fell race across the South West Pennines, 8 km (5 miles) with 213 m of climb and rewarding views. Entry is on the day via Earby Cricket Club for a modest fee and teams of three are welcome.

Waymarked one-lap trail runs in Sherwood Forest offering 30.8 and 40.8 mile routes with regular aid stations, marshals and a 10.5 hour cut off. The loop passes Creswell Crags, Clumber Park and several estate grounds.

Returning for its 10th edition, the Spire Ultra is a **33 mile** trail around Chesterfield following much of the Chesterfield Round Walk. The varied route includes moorland, woodland and farmland; checkpoints supply water and some food, wit..

Circular challenge routes of 26, 23 or 18 miles around the Colne Valley, starting and finishing at Marsden Parochial Hall. Entry via SiEntries; places are limited and the fee includes checkpoint refreshments and a finish meal.

A self-navigated trail run around Delph of about 18 to 19 miles with roughly 3000 ft of ascent, visiting five trig points and using footpaths including parts of the Pennine Way. The unmarked course has three manned checkpoints and mandatory..

A point to point fell event from Castleshaw Centre visiting five trig points over roughly *31.5 km / 19.6 miles* with about 900 m ascent. The unmarked anticlockwise route includes three manned checkpoints and requires full FRA kit.

Take on The Tour of Bradwell The Other Half, a challenging fell race in the Peak District starting and finishing at Bradwell Sports Club. Expect a long high ground route with big climbs and a lively mass start atmosphere.

A 14 miles AL category fell race from Downham around Pendle with 1250 m ascent, nine checkpoints and route choice across seven cloughs. The event is FRA registered and requires full FRA mandatory kit at registration.

Cressbrook Crawl on Saturday 9 May 2026 invites runners to tackle the Peak District in a 10.5 km fell race with 400 m of climb from Cressbrook Club. Pre entry is required, so sign up early for a scenic and gritty hill challenge.

Trail marathon, half and 10k set on circular routes from Sutton Bank Visitor Centre on 10 May 2026; courses are untaped so competitors use downloadable maps and must carry mandatory safety kit.

A fell running event in the North York Moors on 10 May 2026 covering 18.2 km with 950 m of ascent. Entry is on the day for cash only and teams of three are allowed.

Trunce 3 at Oxspring Playing Field on Mon 11 May 2026 offers a scenic but hilly 6.2 km senior race with 190 m of climb in the Peak District. Entry on the day is £3 with a 3 km over 10 junior race included, part of an eight race series.

Evening trail races at Constable Burton Hall on 14 May 2026 offering 5km run, 5km walk and a 10km run across pasture, tracks and woodland. The course is marked and includes water stations, parking and post race food options.

Join Rodley Rock up n' Run for a friendly pop up summer race along the Leeds and Liverpool Canal behind the Rodley Barge Pub. Pick a 5k or 10k and celebrate with hot food, a beer and a jumble medal in relaxed village company.

Join the Hayfield May Queen fell race on Fri 15 May 2026 for a lively village run as part of the May Queen celebrations and the 3 Days in May series. Entry is on the day, with all proceeds supporting the May Queen charities.

An approximate 10K undulating trail race on 15 May 2026 near Skellingthorpe Pavilion with chip timing, medals and goody bags. The course is unsuitable for wheelchair users or runners with dogs and entries close on 01/05/2026.