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Trail Running Calendar near Chislehurst 2026-2027

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Explore the top trail runs near Chislehurst for 2026-2027! We've gathered 173 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

May 2027
A guided 12.5 mile trail run around Box Hill that gains about 1000 metres of elevation across woodland, heathland and open fields. Group pace with technical climbs and scrambling and a chance of an alcohol free beer at the finish.
A ten hour, ten lap endurance challenge at Denbies Wine Estate with roughly 3, 4 or 5 mile loops and graded medals and shirts based on the shortest loop completed.
A two day self supported navigation challenge for teams of two through the Surrey Hills with basic farm camping and virtual controls.
Nuclear Rush is a May obstacle race at the Secret Nuclear Bunker Estate in Essex offering 6 km and 12 km courses with 40+ and 70+ obstacles, plus family and kids races.
Off road 10 km, 5 km and family runs at Milton Creek Country Park on 9 May 2027 supporting The Oliver Fisher Special Care Baby Trust. Varied trail terrain, route maps and event medals are provided.
A multi distance trail event around Bewl Water reservoir near Lamberhurst, Kent. Races include 50km, marathon, half marathon and 10km on wooded trails and country lanes with start and finish at the Visitor Centre.
Inflatable obstacle-course event at Brands Hatch on 15 May 2027 with 2.5k to 15k lap options, music zones, family entries and finishers' medals.
Experience London's energetic Hackney Moves Festival featuring a half marathon on closed roads, a sunset 10K, and a community festival at Hackney Marshes.
A 10th anniversary half marathon and new 10k in Chislehurst that explores local green spaces and raises funds for The Maypole Project.
Trail races of 10 mile and 5 mile at Cammas Hall Farm, Essex on 16 May 2027 with chip timing, water stations and finisher t-shirt and medal.
Race for Life at Weald Country Park in Brentwood features 3k, 5k and 10k routes across grass and woodland trails. The 10k is two laps of the 5k course and the event is chip timed.
Track running event at Wodson Park offering distances from 5k to 50k and a six hour timed challenge on a 400 m lap circuit.
A supported trail challenge from Richmond to Brighton offering distances from 10 km to 100 km with rest stops, GPS tracking, camping, and on route medical support.
June 2027
A point-to-point 50 km trail race along the River Medway from Rochester to Tonbridge with a predominantly flat course, four aid stations and a 9 hour cut-off.
A point-to-point 30 km trail along the River Medway from East Farleigh to Tonbridge with three checkpoints, chip timing, bag transfer and an athletics track finish.
Two supported trail runs in London: a 55 km ultra and a 25 km route on the Capital Ring with signed routes, feed stations, chip timing and finish refreshments.
Community 3k and 5k runs at Dunorlan Park on mainly grass and woodland terrain with some inclines and limited general parking.
A 10 km out-and-back race through gravel paths and woodland at Weald Country Park in Brentwood, organised by MCC Promotions. The event includes on-day registration, water stations, prizes and supports the charity Sport In Mind.
Urban 100 km ultramarathon in central London with 100 km, 50 km and 25 km routes that pass 100+ city landmarks and include staffed checkpoints.
A muddy 5k obstacle course at Cassiobury Park where participants climb, crawl and slide through timed waves while raising funds for cancer research.
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