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 363 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!
April 2027
A trail weekend at Cowdray Estate, West Sussex offering five distances from 12 km to 110 km, low technical difficulty, an event village with expo, and optional camping and race support.
A 50K trail ultra along the Ridgeway in the Chiltern Hills, starting at Berkhamsted Castle and finishing in Wendover, with three checkpoints and a 9 hour limit.
Windsor 50 offers supported looped trail routes of 50 km, 25 km and 10 km from Windsor Racecourse through the Great Park, Thames Path and Runnymede.
Multi-terrain 5 km and 10 km races at Ibstone with routes through Wormsley Estate plus a 1 km or 2 km Run in Colour for ages 4 to 11.
A multi terrain run at Dummer Down Farm on 18 April 2027 offering 10 km, Canicross 10 km and a half marathon with a finisher medal and a Dell pint cup.
A multi day trail series around the Thames offering 250, 150 and 100 mile options with GPX maps, checkpoint support and GPS tracking on mainly canal and riverside paths.
Timed laps at Tilgate Park on 24 April 2027 offering distances from 5 km to ultra with medal and no medal entry options.
A blindfolded navigation challenge in Winchester where participants are dropped at unknown locations and must find their way back on foot. Options include 6 miles for visitors and 10 or 15 miles; no maps or GPS and a sealed emergency bag is used.
An alternative to the London Marathon at Walton on Thames featuring a UKA certified 3.28 mile lap. Options include full and half marathon or a seven hour timed event, with a 150 mm finish medal for participants.
Trail runs of 10 km and 10 miles through Angmering Park Estate bluebell woods and South Downs, with a new finish at The Worlds End and on-course support.
May 2027
A five mile off road race through woods and farmland around Hurstbourne Tarrant in the North Wessex Downs. Organised entirely by volunteers since 2009, the annual event donates all proceeds to local charities.
Four separate 100 mile races between May and October 2027 on the Thames Path, South Downs Way, North Downs Way and Autumn 100.
Three towns host races across a Bank Holiday weekend in 2027, with combined results forming the Mid Sussex Marathon. Distances include 10 mile, 10k, a chip timed mile and a family fun run, plus virtual and combo marathon options.
Guided 30 mile trail run near Guildford on 1 May 2027 following the North Downs Way and Greensand Way, including climbs such as Leith Hill.
Three Forts Challenge is a Sussex trail running event across the South Downs from Lancing Manor Leisure Centre. It offers a full marathon, half marathon and a 5 mile run, and directs event profits to Ferring Country Centre and local charities.
Rapid Relays at Culden Faw Estate on 2 May 2027 offers 4 km loop relay racing for solo runners, pairs and teams amid woodland and Chilterns views.
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.
Spring trail races through Harewood Forest near Wherwell offering 5k, 10k, canicross and a children's fun run on marked, multi-terrain courses.