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 358 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!
September 2026
Experience a scenic trail marathon or half marathon through the Surrey Hills along the historic Pilgrims Way and North Downs Way.
A wine-themed running event at Denbies Wine Estate near Dorking offering a half marathon and 10 km through vineyards with wine stops, food and live entertainment.
A multi-terrain trail race from Rye Sports Centre in East Sussex offering 30k (slightly over 30 km) and 15k routes through the High Weald AONB. The course links historic churches and passes woodlands, orchards, country lanes and coastal views.
Community memorial and fundraiser in Slinfold on 13 September 2026, offering chip timed 10k and 5k trail races plus children's events through scenic West Sussex countryside.
Trail races on rough tracks around Ashtead Common, with a 10 km and a 2 km kids run; proceeds support local charities and the event promotes low environmental impact.
An annual fun run in Steeple Barton offering 10 km, 5 km and a fun run on undulating on and off road courses through lanes, fields and the Barton Abbey Estate. Proceeds support Steeple Barton Church.
Timed laps on a 5.3 km riverside course along the Thames allow runners to build distances from 5 km up to ultras. First 50 entries receive a black and yellow plushie and a Feisty mini me medal; a no medal option is available.
A 10 km run through the private parkland of Chevening Estate in Sevenoaks with timed results, finisher medals and official race photography.
A one-day event on 13 September 2026 in Ashtead offering guided trail runs for women, workshops on confidence and safety, panel talks, kit trials and a raffle.
Seven hour Time Challenge along the River Thames in Staines offering lap based distances from 3km to ultra, with medals, pins, aid stations and goody bags.
A single loop 50 mile race through the Chiltern Hills with 5600 ft of climb, five aid stations, full medical cover and a 13 hour cut off on 19 Sep 2026.
Experience the historic trails of Kent with 25km, 50km, or 100km races featuring scenic woodlands, castle views, and a festival style race village.
Trail running at Hambledon Vineyard with races from 1 km to 20 km, vineyard facilities, chip timing and charity fundraising.
Trail event at the Cricket Green offering 1k, 5k and 10k distances with chip timing, medals, onsite music and food, raising funds for local charities.
A 12 km team navigation endurance challenge along the Seven Sisters and South Downs Way with load bearing and non load bearing categories.
Run a 13 km route through the rolling hills and woods of the South Downs near Lewes to support local wildlife and land conservation efforts.
Community fun run in Horsted Keynes with 2.5K, 5K and 8K countryside routes; proceeds split between the school PTA and Rocking Horse Children’s Charity.
BigSky is the "Air" event in the Classic Element Trail Series on 20 September 2026 at Hyde Common, New Forest. Routes of 18 miles, marathon and 50k run over marked trails with multiple aid stations, mandatory fluid carriage and a bespoke finishers me..
A technical looped forest trail at Avon Tyrrell in the New Forest with choices from 5K to ultra, on-course aid, facilities and a finisher medal.
A 7k beach run from Broadstairs to Ramsgate and back with individual and team prizes, live results and on-site refreshments.