Trail Running calendar near Chesterfield 2025-2026

We have found 589 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.

Run the Bronte Way fell race through the South/West Pennines, a scenic 12 km point to point with 351 m of climb. Pre entry only with limited bus support and a warming soup and roll at the finish make this a classic autumn challenge.

Take on The Drop in Manchester, a blindfolded navigation challenge where teams or solo runners are bused to a secret drop and must find their way back on foot. Choose 10 or 15 mile options for a unique test of navigation and grit.

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.

Experience Irchester Spooktacular, a Halloween night time run through woodland trails with 5k and 2k family options. Fancy dress, themed marshals, medals, Halloween treats and free photos make it a spooky family favorite.

Run the Hubble Bubble & Ghostly 1 Mile along the scenic Leeds Liverpool Canal for spooky family fun or longer distances up to an ultra. Fancy dress is encouraged with spot prizes and finishers get bespoke Halloween medals and sweet treats.

A classic Pennines fell race, Race You To The Summit is a 7 km course with 260 m climb from the Summit Inn out and back to the White House pub. Expect rugged views, quick times and Halloween fancy dress fun.

Tackle the Monsal Mash in the Peak District, a challenging 9.5 km fell race with 500 m of climb over technical and fast rough terrain. Advance entry and full kit required, teams of three welcome.

November 2026

Enjoy a 5 mile trail through scenic Sankey Valley Park in St Helens on Sunday 1 November 2026, with compact but sometimes muddy terrain and marshals on course. Runners must be 15 or older and all finishers get a goody bag memento.

Run a 5 mile Night or Dawn route on Brampton Valley Way and pass through the atmospheric 422 m Oxendon Tunnel. Earn an interlocking event medal, enjoy post race refreshments, and support local foodbanks.

Run under the stars around Swinsty and Fewston Reservoir on 7 November 2026 with 3 mile and 6.7 mile loop options. Well marshalled and signed, this low light trail needs a head torch and rewards finishers with a bespoke medal and treats.

Swinsty & Fewston Lakeside Dash invites you to run scenic, undulating woodland and off road trails around the reservoirs near Otley on 7 November 2026. Distances from 10km to marathon, with marshals, aid stations and a bespoke finisher meda..

Challenge yourself on the Shepherds Skyline Fell Race in Todmorden, a rugged 10 km with around 350 m of climb featuring a steep descent off Stoodley Pike and a tough return climb. On the day entries only and mandatory fell kit is required.

Take on the Burley Moor Run in Burley in Wharfedale, a scenic 11 km (6.8 miles) test across moorland with 250 m of climb. Open to runners aged 16 plus, with entries available in advance or on the day.

Soyland Moor CragRunner on Sun 8 Nov 2026 is a 22 km fell race with 440 m ascent from Cragg Vale. Expect self navigation, rough moorland and checkpoints including Stoodley Pike and Manshead Head. Full kit and experience required.

Run Bolton Abbey on 8 November 2026 offers scenic, hilly trails through Bolton Abbey with distances from a family 2.4 mile to a half marathon. A Remembrance Day silence will be observed and proceeds support Sue Ryder Manorlands Hospice.

Tackle a classic Peak District fell race around the Roaches and Shutlingsloe: 15 miles with over 1100 m of climbing across rugged, scenic terrain. On the day entry is available for £15 and includes a hot meal, perfect for adventurous runner..

Join Leg It Round Lathkil on 8 November 2026 for a scenic 11.5 km fell race in the Peak District with 290 m of climb from Lathkil Hotel near Bakewell. Entry on the day and all proceeds go to Children in Need; wash shoes for biosecurity.

The Wadsworth Half Trog will take place in Hebden Bridge on Sunday 8 November 2026. You can run between 9 and 15 kilometers.

Run the scenic Wharfedale Skyline around Otley and Ilkley on 14 November 2026, choosing 13, 20 or 35 mile courses past Cow and Calf Rocks and Lindley Wood Reservoir. Finishers receive a medal and event T shirt.

UTMB Index

Join the Yorkshire Weekend Saunter Series in Kirkstall on 14 November 2026 for scenic canal runs along the Leeds Liverpool Canal. Choose 5K, 10K or Half Marathon and finish with a jumble medal, hot food and a beer or soft drink.