Trail Running Calendar South East (England) 2026-2027

A trail festival in Winchester on 4 May 2026 offering four distances from 14 miles to a 50K ultramarathon, fully marked routes, aid stations and parking at Winchester Rugby Club.

Take on the Freddo Mercury Rhapsody Run along a flat riverside towpath at Xcel SPORTS HUB, logging as many 5.3 km laps as you can within a relaxed 7 hour limit. Rock up in a 1.5 hour start window or request a time, with aid stations and opt..

Spring trail races in Harewood Forest featuring 5k, 10k, canicross and a children's fun run on undulating forest and field routes. Pre-registration only; proceeds support local playing fields and school PTA.

A 100-kilometre anticlockwise loop through the Chiltern Hills, the race follows The Ridgeway and local trails with six checkpoints, marked navigation and open GPS tracking. The event is based in Chesham and limited to 250 runners.

A point to point 50 km ultramarathon from Horsham to Brighton seafront on 9 May 2026, featuring multi terrain trails, four feed stations and a 9.5 hour cut off. Individual and two runner relay entries are offered with team prizes.

Goring Gap Trails offers ultramarathon, half marathon and walking distances near Reading on 9 and 10 May 2026. The TRA licensed event includes affiliated and unaffiliated entry options and on site camping.

Inflatable 5K in Guildford on Saturday 9 May 2026 is an inflatable obstacle course at Stoke Park offering 2.5k laps with options of 2.5k, 5k, 10k or 15k and family friendly participation rules.

Test your endurance at Stanmer Park by completing 4.167 miles every hour until only one runner remains. This out and back course offers a personal challenge with support facilities and refreshments for all participants.

A riverside event at Wraysbury Skiff & Punting Club offering 10 km, half marathon and marathon courses along the Thames Path with marked laps, marshals, a bespoke finishers medal and prizes for top finishers.

Experience the twilight beauty of Ardingly Reservoir during this evening run in West Sussex. Choose between a 5K or 10K distance on an undulating trail course featuring scenic water views and a finisher medal.

Off-road 10k, 5k and junior runs at Milton Creek Country Park on 10 May 2026. The event supports the Oliver Fisher Special Care Baby Trust and includes medals, prizes, pacers and limited free on-site parking.

Trail races at Rathfinny Wine Estate on undulating off road loops with marked routes, aid stations and recycled finisher medals. The carbon neutral event supports the WOLO Foundation and offers single and double loop options.

Trail races in the South Downs around Cocking on 10 May 2026, offering 10 km and 20 km senior courses plus 3 km and 5 km junior races on mostly off road trails with water stations, marshals and age category awards.

Hairy Legs is an all ages cross-country event at Sheepcot Recreation Ground on 10 May 2026, with children's laps, teenage and adult loops plus solo and relay options, and proceeds supporting two local primary schools.

A one lap *10 km* trail through Hampton Estate and Puttenham Common with undulating hills and bluebell woods. Chip timing, finish medals and on-site parking, with food and refreshments available at the finish.

A community 5k trail run and walk around East Hendred with a separate 1k kids event on the Sportsground. Entries are limited and close on 8 May 2026.

A four-race summer series at Dinton Pastures offering 5 km, 10 km and a 2 km kids event across May to August. Organised by Barnes Fitness with chip timing, marshals, medals and pre bookable parking.

A 50 mile point to point run on the North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb, six aid stations and a 13 hour limit. Entry requires a prior marathon finish within that race’s cut off.

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 Race Track on Saturday 16 May 2026 with 2.5 km laps and distance options to 15 km, music zones, water stations, on-site parking and charity partners.