Trail Running calendar near Chessington 2025-2026

The Henley River Half Marathon, 10k & Junior Race takes place in April 2026 at Temple Island Meadows, Henley-on-Thames, UK. This scenic event features a mixed-terrain, undulating course along the Thames, starting and finishing at the iconic Royal Henley Rowing Regatta launch point. The half marathon..

The Rosebud Marathon is a scenic 26.2-mile race held in Northamptonshire, England, featuring a mix of approximately 60% trails and 40% roads. Starting at Hartwell and finishing at Brixworth Country Park near Northampton, the course traverses beautiful countryside, including canal towpaths and 14 vil..

The Rose of the Shires Ultra is a scenic 54-mile circular ultra marathon held in Northamptonshire, starting and finishing at Brixworth Country Park. The course features approximately 72% trails, including country paths, towpaths, and forest tracks, with the remaining 28% on roads. Runners traverse b..

The 50 Mile Grand Slam is a challenging endurance event organized by Centurion Running, comprising four separate 50-mile races held throughout 2026 in the UK. Participants complete the South Downs Way 50, North Downs Way 50, Chiltern Wonderland 50, and Wendover Woods 50. The event covers diverse sce..

Run The Seasons at Cowdray is a scenic trail running event held on the Cowdray Estate in West Sussex, within the South Downs National Park. The 2026 Spring edition features courses of 5km, 10km, 10 miles, and dog-friendly canicross options. The route traverses Ambersham and Heyshott Commons, designa..

The Centurion South Downs Way 50® is a challenging 50-mile foot race held annually along the South Downs Way National Trail in Southern England. Starting in Worthing and finishing with a lap at Eastbourne Sports Club Athletics Track, the course features 5,700 feet of elevation gain over 85% trail an..

The Haughley Festival of Running is an annual event held at the exclusive Haughley Park in Suffolk, offering a range of race distances including 5k, 10k, Half Marathon, Full Marathon, and Ultra Marathon. Now in its fourth year, the festival provides an intimate and self-contained setting with exclus..

The Windsor 50 Ultra Challenge is a premier UK trail running and trekking event held at Windsor Racecourse. Participants can choose from 50 km, 25 km, or 10 km looped routes that showcase scenic views of Windsor Castle, the Great Park, Runnymede, and the Thames Path. The 50 km course features two di..

The Spring Trail Series by Ultra X is a trail running event held at the Cowdray Estate in Surrey, within the scenic South Downs National Park. The series features five race distances: 12km, 25km, 50km, 50 miles, and 110km, all starting and finishing at the same accessible location near Cowdray Farm..

The Chiltern Ridge Classic 50K is an iconic ultra marathon held in the Chiltern Hills, UK, featuring a challenging 51 km trail run with 996m of elevation gain. The race starts at historic Berkhamsted Castle and finishes at Hampden Meadow in Wendover, traversing scenic ridgeline trails including Ashr..

The Thames Ring 250 is a challenging 250-mile (approximately 256 miles) trail ultramarathon starting and finishing in Streatley-on-Thames, UK. The race follows an anti-clockwise loop along the Thames, the Grand Union Canal, and the Oxford Canal, primarily on flat canal and riverside paths. Despite t..

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..

The Garmin UK Trail Running Festival 2026 takes place at St Giles House, Wimborne St Giles, offering a variety of trail running events including a marathon, half marathon, 10K, 5K, and junior races for children as young as 0 years. The festival features scenic courses designed to inspire runners to..

The Other Run, organized by Zig Zag Running, takes place at the Suffolk Running Centre in Bury St Edmunds, coinciding with the London Marathon day. It offers multiple distance options: 5k, 10k, half marathon, and full marathon. The marathon follows the officially measured, scenic, and mildly undulat..

The Drop - Winchester is a unique and challenging race held in Winchester, UK, offering participants a choice between 10-mile and 15-mile distances, either solo or in teams. Inspired by military-style navigation, the event requires runners to find their way back to the event center from an undisclos..

The Centurion Thames Path 100 is a 100-mile continuous trail race held annually, with the 15th edition scheduled for May 2026. The point-to-point course runs from Richmond in South West London to Oxford city center, finishing on the grounds of Oxford University. The route follows the scenic Thames P..

The Isle of Wight Ultra Challenge is a premier endurance event held on the stunning Isle of Wight, featuring a variety of distances including 106km, 53km, 25km, and a 10-mile option. Participants walk, jog, or run along the island’s spectacular southern coastal path, passing iconic landmarks like th..

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..

Tempo Trail Races 2026 is a weekend trail running event held in the scenic Cotswolds, based at Ilmington Sports & Social Club near Shipston On Stour. The event offers a variety of race distances to suit different levels, including a 100K Ultra, a new 50K Ultra, a Marathon, a Half Marathon, and a 10K..

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..