Trail Running calendar near Chesterfield 2025-2026

We have found 407 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.

Tackle scenic moorland trails from Hare & Hounds to Peel Tower at Holcombe 10 on 16 May 2026, with 10K and 10 Mile options across Redisher Woods. Expect tough climbs, stunning views and a finisher memento.

Take on the Pommie Panter Fell Race in Youlgrave, Peak District, a rugged 5.8 mile route with climbs, limestone descents and marshy sections finishing on the village high street. All profits support local village facilities and a friendly c..

SilverBackTrails Oswiu’s Revenge Half Marathon is a scenic trail around Black Hambleton and Silton Woods near Osmotherley on 17 May 2026. With only 50 places, it promises a small friendly field and spectacular moorland views.

Tackle the Leaden Boot Challenge: a scenic 26.2 mile walk or run around the White Peak from Alstonefield with about 4,800 feet of climbing. Enjoy checkpoints, hearty finish fare, and support for local charities.

Run a scenic flat 10K through Golden Acre Park and trails in Cookridge, a single lap route past Paul's Pond and woodland. Places are limited to 360 and proceeds support Cancer Research UK and local community groups.

Take on Gods Own Backyard Ultra Spring 2026 in Leeds, an hourly loop challenge across towpath, woodland and farmland where runners keep going until one remains. Camping, marshals and a Yorkshire goodie bag add local charm.

Grim Reaper Running Festival at Grimsthorpe Castle Estate on 23 and 24 May 2026 features races from 10 to 100 miles and a 100 mile team relay. Camp on site and run a scenic 10 mile loop through ancient woodland and lakeside trails.

UTMB Index

Panopticons Ultra is a point to point trail ultra in East Lancashire on 23 May 2026, covering about 32 miles and visiting four iconic Panopticons art installations. Expect big climbs, rugged Pennine trails and dramatic views for experienced..

Take on the Grand Union Canal Race, a nonstop 145 mile ultra from Birmingham to Little Venice along scenic towpaths. Limited to 100 starters with a 45 hour limit, it welcomes supported and unsupported runners for a true canal challenge.

Event overview Get the Hull out of Here is a trail running event based at Pelican Park Recreation Ground, Lambwath Road, Hull, HU8 0EE. The next race is scheduled for 24/05/2026. The course follows the TransPennine Trail and the Hornsea Rai..

Join the Yorkshire Weekend Saunter Series at the Fisherman Inn in Bingley for scenic, relaxed runs where you can run, jog or walk at your own pace. Choose 5K 10K or half marathon and enjoy a jumble medal, hot food and a drink at the finish.

The The Maverick Peak District Trail will take place in Bakewell on Saturday 30 May 2026. This trail is organized by Maverick Race. You can run between 10 and 52 kilometers.

A scenic 5.5 mile memorial fun run from Worksop College through Clumber Park, with marshals and a finisher medal. Organised by Worksop Harriers, the event supports Cancer Research and welcomes runners aged 16 and over.

Settle Saunter in the Yorkshire Dales on 31 May 2026 offers 10k, half marathon and 23 mile routes across scenic footpaths and bridleways. Run by the Rotary Club to raise funds for local and global charities, with a cafe on site.

Take on scenic trails at Tatton Park on 31 May 2026 as part of the Wild Hybrid Weekend, with 10 km and half marathon routes across grass, woodlands and paths. Canicross welcome and all finishers get a medal, Wild Deer merch and refreshments..

June 2026

Join Race 2 of the Jane Tomlinson Canal Race Series on 2 June 2026 in Methley for a fast 5 km on the flat Aire and Calder towpath. Enjoy a friendly marshaled event with prizes and proceeds supporting the Jane Tomlinson Appeal.

Join the Griffin Challenge at Braybrooke Taproom on 3 June 2026, a six hour looped event on the Griffin Trail where runners, walkers and hikers do as many laps as they like. Celebrate after with coffee, pastries and a cold beer.

The National Forest Way Ultra will take place in Burton upon Trent on Saturday 6 June 2026.

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Join the Divorce Day Defib Fundraiser for a fun, scenic run from Coalport Village Hall along the Silkin Way and over Ironbridge. Choose 8, 16 or marathon distances and embrace fancy dress with top hats and tiaras to boost spirits.

Take on a 24 hour 50 mile traverse from Marsden to Ilkley across South Pennine moors, visiting six poetic Stanza Stones and the historic village of Haworth. Expect rugged climbs, live tracking and hearty checkpoints to keep you moving.