Trail Running Calendar South East (England) 2025-2026

The Drop - Winchester is a unique and challenging race held in Winchester, UK, offering participants a thrilling test of resilience and navigation skills. Competitors choose between a 10-mile or 15-mile course, either solo or in teams. The race begins with a blindfolded bus ride to an undisclosed dr..

The Ale Trail is a 15-mile fun run held in Alfriston, East Sussex, starting from the beer garden of Ye Olde Smugglers Inne. The event features a scenic course with two checkpoint pubs—the Hampden Arms and The Ram Inn—where runners can enjoy a beer and snacks before continuing. Participants are encou..

Rapid Relays is a dynamic running event held at the scenic Culden Faw Estate in Fawley, near Henley on Thames, Oxfordshire. The race features a woodland trail course on estate tracks with gently undulating terrain, including a notable climb before 3 kilometers followed by a long downhill stretch bac..

The Three Forts Challenge is a renowned trail running event held in West Sussex, starting and finishing at Lancing Manor Leisure Centre. It offers three race options: a full marathon (27.2 miles), a half marathon, and a 5-mile trail run. The courses feature demanding terrain with steep climbs, stile..

BigWayRound - Winchester is an award-winning, Gold-rated trail running event held at Winchester Rugby Club, offering four distances: 14 miles, 19 miles, a marathon, and a 50K ultramarathon. The course showcases stunning English countryside, including trails along the Itchen Navigation, ascents past..

The Chiltern Hills 100K is a 100-kilometer ultra marathon held in the Chiltern Hills, Buckinghamshire, UK. The race features an anticlockwise loop starting and finishing in Chesham, passing iconic landmarks such as Ashridge Estate, Coombe Hill, Whiteleaf Hill, Bledlow Ridge, and Great Hampden. With..

The Run to the Sea Brighton Ultramarathon is a scenic 50km point-to-point race from Horsham to Brighton seafront, featuring a mix of trails and rolling downs. Known for its stunning views and well-organized setup, it caters to both beginners and experienced ultramarathoners. The course is fully sign..

The Centurion North Downs Way 50® is a challenging 50-mile point-to-point ultramarathon held annually along the North Downs Way National Trail in Southeast England. The race starts in Farnham, Surrey, and finishes at Knockholt Pound near Greater London, featuring a total elevation gain of 5,600 feet..

The Reigate Priory Park 10K is a scenic charity fun run held in Priory Park, Reigate, Surrey. The course features a 250-meter start plus four laps on an accurately measured, gently undulating cross-country terrain surrounded by lush greenery. Suitable for runners of all levels, the event fosters a f..

The London 2 Brighton Ultra Challenge is a premier endurance event in the UK, offering multiple distances including 100km, 75km, 58km, 42km (Sussex Marathon), 25km, and a 10km option. Starting mainly from Richmond-Upon-Thames, participants traverse the scenic North Downs and Surrey & Sussex countrys..

The South Downs 50k is a point-to-point trail race from Falmer to Eastbourne, running mainly along the South Downs Way through the stunning South Downs National Park in Southeast England. Covering 50 kilometers with over 3,500 feet of elevation gain and descent, the course features mostly runnable g..

The Beat the Sunset 50km ultramarathon takes place in Maidenhead, Berkshire, starting and finishing at the NMCC Sports Club. This multi-terrain course is fully marked and features four checkpoints approximately every 10km, with a personal nutrition drop available in the latter half. The event offers..

The Castle Trails 30km is a scenic point-to-point trail race in Kent, launching in 2026 as part of the Three Castles 50km Ultra weekend. Starting at Little Fant Farm near Maidstone and finishing in Tonbridge, the course follows the River Medway, passing historic sites like East Farleigh’s stone brid..

The Three Castles 50km Ultra Marathon is a scenic race held in Kent, England, starting in Rochester and finishing at Tonbridge athletics track. The flat course follows the River Medway, passing three medieval castles, charming villages, and lush countryside along the Medway Valley Walk. Runners expe..

The YHA 14 Mile Trail Run is an annual trail running event held in the Southease area, accessible via the Lewes-Seaford train line. The challenging 14-mile course begins with a climb and features slippery, muddy, and chalky terrain, making trail shoes recommended. Participants receive bottled water..

The RunThrough Marlow Trail Run, taking place on June 28, 2026, is a scenic off-road event set in the Thames Valley, starting at Marlow Rugby Union Football Club. It offers three distances: Half Marathon (1 lap, 53m elevation), 10K (1 lap, 23m elevation), and 5K (2 laps, 20m elevation), all on trail..

The Maidenhead Trail Run, held on July 26, 2026, offers a scenic and relaxed running experience in Summerleaze Park, Maidenhead, UK. Participants can choose from 5K, 10K, and Half Marathon distances, all featuring flat, soft trail terrain ideal for runners of all levels. The course loops around peac..

The Windsor Trail Run, held on August 30, 2026, takes place in the scenic Alexandra Gardens, Windsor, UK, with views of Windsor Castle. This event offers two race distances: a 10K and a Half Marathon, both featuring flat, trail terrain with minimal elevation (29m for 10K and 58m for Half Marathon),..

The Henley River Half Marathon, 10K & Junior Race takes place on September 5, 2026, at Temple Island Meadows, Remenham Lane, Henley-on-Thames, UK. This event features a half marathon, a 10K, and a junior race, all set along a scenic route by the Thames. The course offers mixed, undulating terrain wi..

The Windsor Trail Run, taking place on November 8, 2026, is a scenic trail running event set in Alexandra Gardens, Windsor, Berkshire. Offering both 10K and half marathon distances, the course features flat, off-road trails with gentle elevation gains (29m for 10K and 58m for half marathon), ideal f..