Trail Running Calendar South East (England) 2026-2027

A 50 mile point to point ultramarathon along the North Downs Way with 5,600 ft of ascent, six aid stations and a 13 hour cut off. The route is mostly trail and requires specific qualifying and mandatory kit.

The Twenty Sixth Compton Downland Challenge in Compton, Berkshire on 16 May 2026 features a full marathon and a 16 mile race with a seven hour time limit; route maps, elevation profiles and videos are provided.

An inflatable obstacle course at Brands Hatch on 16 May 2026 offering laps of a 2.5 km circuit with 2.5 km, 5 km, 10 km and 15 km options, music zones, water stations and a finisher medal.

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

A two day Spartan Trifecta weekend in Henley on Thames on May 16 and 17, 2026, featuring Sprint, Super, Beast and Kids races along town landmarks and the riverside. Team entries and spectator tickets are available.

A cross-country *10 km* race at Priory Park, Reigate on 17 May 2026, organised by MCC Promotions with on-day registration, hydration stations, basic facilities and support for the charity Sport In Mind.

Explore the scenic parish of Deddington on a 5k, 10k, or 20k run through local farmland. This community event supports local schools and the Firefighters Charity while welcoming runners of all abilities.

The Ridge Off Roader is a trail run through the scenic Chiltern Hills. It offers a half marathon and a 10k route, plus a fun 1k for kids. All proceeds support the local school.

Off-road multi lap run at Nutbourne Vineyards with views to the South Downs. Choose distances from 5 km up to a half marathon on the day; entry is £29, places are limited to 100, and finishers receive a medal, drink and cake.

Held at Blenheim Palace on 17 May 2026, the event offers a 7k (7.4k) lakeside route, a separate dog race, a 4-mile buggy and wheelchair route, and a 1-mile junior run.

Mud Monsters Run on 17 May 2026 in East Grinstead is a muddy obstacle event with 3 km, 5 km and 10 km routes through fields, woods and river crossings. Finishers get a medal and free photos; onsite parking costs £5.

Three Beaks Trail Running Day offers three self supported trail routes from Beak Brewery in Lewes on 17 May 2026. Routes are unmarked but run leaders guide groups and each finish includes a complimentary drink.

Dragon's Eye Race 1 2026 at Hurtwood Park Estate offers looped off road laps over mostly flat trails with a seven hour time limit. Participants can run from 5 km up to ultra distance and receive a bespoke finishers' medal.

A point-to-point 50km trail race from Falmer to Eastbourne along the South Downs Way, covering roughly 3,500 feet of ascent and descent with mostly runnable trails, four aid stations, live GPS tracking and no qualifier required.

A point to point trail run in Surrey on 23 May 2026 offering 62K, 41K, 20K and relay options. The event finishes in Godalming with a race village, timed results, medals and free race photos.

A single loop trail half marathon around the Seven Sisters in the South Downs National Park, starting and finishing at Helen Garden in Eastbourne. The 13.5 miles route includes about 2,000 feet of ascent on mostly trail surfaces.

Run a flexible distance along Winchester's scenic Itchen Way. Choose your laps from 2.62 miles up to an ultra within a 7-hour window, with a famous aid station and a finisher's medal for all.

An event covering 100 miles over the Spring Bank Holiday Weekend from Meopham through the North Downs, Greensand Ridge, Weald and Ashdown Forest, visiting places from the Winnie the Pooh stories. Entries are closed and minimum age is 18.

Experience the twilight beauty of Ardingly Reservoir during this sunset run in West Sussex. Choose between a 5km or 10km distance on a scenic undulating trail and enjoy a timed midsummer evening event with finishers medals.

A guided 15 miles trail run from Cuckmere Haven to Beachy Head on Saturday 23 May, organised by Trail-Run Explorers. The event is listed at postcode BN25 4AD and is part of the organiser's programme of guided runs.