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 400 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!
May 2027
Brighton Backyard Ultra at Stanmer Park is an hourly 4.167 mile loop repeated until one runner remains, with entries including a medal, winner trophy, rest pitch, water and snacks.
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.
Trail races through Rathfinny Wine Estate with single 10.7 km and double 21.4 km loops, marked off-road terrain and chip timing. The carbon neutral event supports the WOLO Foundation and provides aid stations, recycled medals and parking arrangements..
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.
A chip timed 5 km and 10 km road and trail race at Haddenham Community Junior School on 9 May 2027 with early bird entries and optional event T shirts.
Two days of obstacle racing in Henley-on-Thames with Sprint 5 km, Super 10 km, Beast 21 km and kids races along the riverside.
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.
A 50 mile point-to-point trail race on the North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb, six aid stations and a 13 hour cut-off.
Several distances are available: 5k, 10k and 20k routes around Deddington. The event is open to all ages and organised to raise funds for Deddington Primary School PTA, Deddington PFSU and the Firefighters Charity via Deddington Fire Station.
Looped trail event at Wiston Estate with a marked 10K circuit and distances from 10K to 100K, plus aid stations, a dedicated 100K area and on-site camping.
A coastal relay event on 16 May 2027 based at The Valiant Sailor and Lilly Roo's in Capel Le Ferne, CT14 0AT, organised as a team relay along the coast.
A weekend of waymarked trail runs and walks at Mapledurham House near Reading, featuring ultras, a half marathon and supported marathon-length walks.
A 7 km cross-country fun run at Trenchmore Farm on 22 May 2027 with music, burgers and a free drink for each runner.
A 50 km multi terrain ultra in Maidenhead along the Thames Path, Jubilee River and Green Way with chip timing, four aid stations, live tracking and a cut off of 8 hours 57 minutes.
Trail races on the Fox Way around Godalming, Surrey, offering 62K, 41K and 20K routes with cupless aid stations and chip timing.
A 5 km obstacle event at War Memorial Park on 23 May 2027 where participants climb, crawl and slide across mixed grass and path terrain; entrants must be 13 or older and a minimum fundraising target of £50 applies.
A guided trail half marathon around the Surrey Hills, about 13 miles from St Martha's Hill in Guildford, following parts of the North Downs Way and notable viewpoints. The run is social in format with a guided pace and evening options.
A 50km point to point trail from Falmer to Eastbourne along the South Downs Way, with about 3,500 feet of ascent, four aid stations and live GPS tracking.
An 86 mile point to point 139 km trail race along The Ridgeway from Ivinghoe Beacon to Avebury with GPS tracking, eight checkpoints and a 28 hour time limit.
A 60 km point to point ultramarathon along the Ridgeway National Trail from Ivinghoe Beacon to Ridgeway View Campsite with marked route and four checkpoints.