South East (England)
Trail Running Calendar South East (England) 2026-2027
Explore the best trail runs in South East (England) for 2026-2027! Our updated list features 391 exciting trail runs across the region. Find your next trail run in South East (England) below and join the trail community at these great events!
October 2026
A lap based Friday timed run on the Thames towpath offering distances from a single 3.28 mile lap up to ultra distances, with the ten pound charity entry supporting Rays of Sunshine and a special double sided medal.
Looped trail event from Maidstone with supported 50 km, 25 km and 10 km routes, covered rest stops, camping and on course medical support.
Trail races around Box Hill in the Surrey Hills offering three distances, steep climbs, aid stations and chip timing from a base at Box Hill National Trust.
A 10 hour, 10 lap endurance event at Pippingford Park with 3 mile, 4 mile or 5 mile loop options and up to 700 ft climb per lap; finishing grade is based on shortest loop.
Military style obstacle mud run at Hever Castle Kent with 3 km, 6 km and 12 km options and many obstacles modelled on Royal Marines training.
Trail running in Hurtwood Forest near Guildford with 15 km and 21 km routes, on-site facilities, water stations and medals for all.
Trail races at Cowdray Estate on 10 October 2026 offering 10 mile, 10 km, 5 km and a new 3 km kids run alongside Cowdray Farm Shop Apple Day.
Four seasonal trail events at Cowdray Estate offering 3 km to 10 mile options, CaniRun and kids races with series scoring, prizes, linking medals and free photos.
A mixed-terrain 10 km and 5 km race around Frieth in the Chiltern Hills featuring woodland paths, country roads and notable climbs.
A single lap 10 km trail race through Limpsfield Common and the High Chart, mostly off-road with varied slopes, a water station at about 5.5 km, and finisher T-shirt and medal.
Community-supported trail runs at Old Basing offering 10K and 6K chip timed races plus a 2K fun run to raise funds for local schools.
Flat mixed trail races along the Basingstoke Canal and through Wellesley Woodlands with 10 km, 5 km and a 2 km fun run, chip timing and a collectable medal.
A 10 km undulating multi-terrain race from Buckingham Town Centre through Stowe National Trust gardens and countryside, with medals for finishers and local charities supported.
A lap-based out and back run along the Thames in Walton on Thames offering distances from a single 5.3 km lap up to ultra distances with a seven hour limit.
Wacky Run Six in Fareham on 11 October is a themed run with an Army Surplus Special atmosphere, a six hour personal-distance format, themed medals and limited entries.
Biweekly free Sunday morning trail runs from Surrey Trek and Run with varied routes and distances, limited to 10 places per leader.
A lap based Friday timed run on a flat 5.3 km out and back course along the river Thames, with distances from 5 km up to ultra. Both attended and virtual entrants receive a finisher medal.
A 100 mile trail race from Goring and Streatley using the Thames Path and Ridgeway in four 25 mile out and back spurs, with 16 aid stations and a 28 hour cutoff.
An annual 25 km or 50 km countryside challenge in Kent Surrey and Sussex with written route directions, checkpoints, included food and GPX files.