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Trail Running Calendar near Winster 2026-2027

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Explore the top trail runs near Winster for 2026-2027! We've gathered 161 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

April 2027
Two routed trail options from Castleton through the central Peak District on 17 April 2027, supporting the Peak District National Park Foundation.
Trail races of 10K, 15K and half marathon run within Elvaston Castle Country Park across woodland, parkland and riverside paths by the River Derwent.
Trail event at Thoresby Park on 18 April 2027 offering distances from 2km to marathon, canicross options, live chip timing, and on-site parking.
Experience a breathtaking trail run through bluebell woodlands and undulating footpaths with 5km and 10km options starting from Newfield Secondary School.
Marathon and half marathon along the traffic free Tissington Trail in Derbyshire, an out and back route climbing to Parsley Hay then returning to Ashbourne Leisure Centre.
May 2027
A 33 mile trail race following much of the Chesterfield Round Walk through moorland, woodland, reservoirs and farmland. Route notes and GPX files are provided and checkpoints offer water with food at selected points.
Castle & Cake is a trail race in Castleton, Peak District, with a finish featuring local food and drink and proceeds supporting local businesses and nature projects.
Small club supported fell race each May on a hilly 5 mile route around Rainow and Kerridge Ridge, with proceeds donated to local charities.
Trail ultramarathon in Sherwood Forest offering 30 and 40 mile routes with marked trails, aid stations, finish medals and on-course crew access.
A supported 75 miles (120 km) trail ultra from Alrewas to Beacon Hill across three counties, with six checkpoints, a 3-person relay option and UTMB Index 100K recognition.
A 7.5 mile clockwise circuit around Carsington Reservoir offering reservoir and countryside views, bespoke finisher medals and entries for runners aged 16 and over.
A chip-timed 10K trail race through Sherwood Pines on 9 May 2027 with distance markers, a water station, limited entries and cash bonuses for fast winning times.
An off road 10 kilometre race on compacted limestone with a net descent to Cromford Wharf, part of the White Peak Festival of Running and served by event coaches.
Mid-May fell race in Youlgrave, Derbyshire with a 5.8 miles course and 876 ft climb over trails, fields and a swamp, entry £6 and limited places.
A single lap trail of approximately 10 km through Quarry Bank Mill grounds on 18 May 2027, with mixed surfaces, a new flat one mile loop, chip timing and a bespoke finisher medal.
June 2027
A handicapped fell race of about 3.5 miles with 860 feet of ascent, held each Whitsun Tuesday and described as the oldest continuously run fell race in the world. Entrants must be over 18 and the route includes two road crossings.
A last-runner-standing backyard ultra at Far Coley Farm on 4 June 2027: hourly 4.167 mile loops on mixed trail until one runner remains, with an on-site village, limited accommodation, and crew facilities.
A 24-hour trail challenge in Edale where runners complete as many 23.3 km loops (977 m ascent each) as possible. Entries limited to 50 with indoor transition, camping and a single log-cabin option; support, navigation notes and an eco-trophy included..
Trail running from Bakewell Showground into the Peak District with five marked routes from 6 km to 55 km, outposts for most routes, mandatory kit for the longest distances.
A 5 km muddy obstacle course through Graves Park woodland and fields, with start and finish by the animal farm. Organised by Cancer Research UK to raise funds for cancer research, the event includes timed wave starts and onsite parking.
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