Trail Running Calendar South East (England) 2025-2026

Wild Run Cotswolds invites trail lovers to Cornbury Park for scenic, undulating single loop routes from 10K to the marathon plus a six hour 360 challenge. Family friendly, fully marked and marshalled, entries limited to 600 runners.

Enjoy scenic undulating forest trails at Alice Holt with 5k, 10k, Half Marathon and junior distances run over 5k loops. The event is postponed until Spring 2026 and raises funds for GUTS to support bowel cancer detection and research.

Guided 30 miles trail run from St Martha's Hill through the Surrey Hills, passing Box Hill, Denbies Wine Estate and quaint villages. An experienced ultra coach leads this friendly group outing, offering guidance and social challenge.

Explore scenic Kent Downs trails from Maidstone basecamp with 10, 25 or 50 km loops via North Downs Way, River Medway and Leeds Castle. Enjoy full support, camping, timed stops and a finishers medal, tee and fizz.

Tackle rolling climbs and sweeping Chiltern views at the Frieth Hilly 10 km and 5 km Run, set on mixed woodland paths and country roads. Expect a scenic but challenging route between Frieth and neighbouring villages.

Join the Windsor Trail Run on Sunday 8 November 2026 in Alexandra Gardens, Windsor for 10K and half marathon off road routes through royal Berkshire. Chip timed races, friendly marshals, an event village and tasty post race goodies await.

Join a guided 10km trail run around the Devil's Punchbowl in Hindhead, tackling scenic hills with a group pause for the view. Sessions run at about 6 min per km and take place as sunset or torchlit night runs, with headtorch and shoe trials..

Guided 30 miles trail run from Haslemere across ancient woodland, rare heath and valleys with views to the South Downs. Led by an experienced ultra coach, this non competitive group run mixes challenge with spectacular scenery.

Join a guided trail run on Box Hill near Dorking, tackling 12.5 miles and roughly 1000 m of ascent through woodland, heath and open fields. Expect technical sections, some scrambling and a supportive group pace for experienced trail runners..