Chislehurst
Trail Running Calendar near Chislehurst 2026-2027
Explore the top trail runs near Chislehurst for 2026-2027! We've gathered 193 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2027
A family-friendly muddy obstacle run in Brentwood, Essex offering 5 km and 1.5 km routes, on-course obstacles, finish-line facilities and an event village.
A bi-annual series at Bewl Water in Kent offering 10 km, half marathon, marathon and 50 km ultra on mixed trail and country lanes with reservoir views.
Guided 10 km trail run around Silent Pool near Guildford, following parts of the North Downs Way and Netley Heath forest. Sessions run at dusk or at night with headtorches in a led group and a recommended pace of about 10 min per mile.
A Thames Towpath trail event from Putney Bridge to Henley offering 100, 75, 50 and 25 km options plus supported rest stops and camping.
Trail half, 10K and a free 2 km kids run at Denbies Vineyard with wine stations, live music and a post-race party.
Undulating trail races on Ashtead Common on 12 September 2027 offering a 10 km and a 2 km kids run while raising funds for local charities.
October 2027
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
November 2027
Point to point Half Marathon along the Grand Union Canal from Cowley to Cassiobury Park, Watford, on towpaths, trails and woodland. Entry from £35.
A commemorative 7 hour Time Challenge in Staines along the Thames with options from 3 km to ultramarathon distances and medals for finishers.
December 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 fully signed 50 km trail ultra in the Surrey Hills on 5 December 2027, with checkpoints, SportIdent timing and a 10 hour cutoff.