Trail Running calendar near Chessington 2025-2026

We have found 321 Trailruns within 80 miles of Chessington. See below where and when you can find the races.

The Phoenix Denbies Marathon & Half Marathon, held at Denbies Wine Estate in Dorking, Surrey, offers a unique off-road trail running experience on a flat-ish 1-mile loop with slight inclines. Scheduled for June 2026, the event features flexible start times over a 30-hour window, allowing runners to..

The Midsummer Munro will take place in Walton on the Hill on Sunday 21 June 2026. You can run 13 miles.

UTMB Index

The Dunstable Downs Half Marathon is a scenic 21.2 km trail race held at the National Trust’s Dunstable Downs estate in the UK. Featuring over 450 meters of elevation, the course offers a challenging mix of sweeping ridge views, fast descents, and tough climbs, making it suitable for trail runners o..

The Summer Solstice Challenge in Colchester is a unique running event held at the scenic Abberton Reservoir Visitors Centre. Taking place on the longest day of the year, participants run laps of just over 5k on off-road paths around the reservoir, enjoying beautiful countryside views and abundant wi..

Run The Seasons at Cowdray is a scenic trail running event held on the Cowdray Estate in Midhurst, set above the world-class polo fields and overlooking the Cowdray Ruins and South Downs National Park. Participants can choose from 5km or 10km distances, including dog-friendly canicross options. The..

The Colworth Marathon Challenge is a unique running event held at the scenic Colworth Estate in North Bedfordshire, UK. It features three races over three days, combining distances of 5 miles, 8.1 miles, and a half marathon of 13.1 miles, totaling the full marathon distance of 26.2 miles. The event..

The Cock-a-doodle Dawdle, organized by Zigzag Running, is a trail running event held at the scenic Hyde Hall Farm in Buntingford, Hertfordshire. Now in its third year, the race offers multiple distance options including 5k, 10k, 15k, Half Marathon, Heavy Half Marathon, Full Marathon, and Ultra Marat..

The RunThrough Marlow Trail Run, held on June 28, 2026, takes place at Marlow Rugby Union Football Club in the scenic Thames Valley. This off-road event offers three distances: Half Marathon, 10K, and 5K, with the 5K consisting of two laps and the others one lap each. The trail features well-marked..

July 2026

The Full Essex Way Ultra is an 82-mile ultra-marathon starting at Epping tube station in London and finishing at the high lighthouse in the historic port of Harwich. The race follows the scenic Essex Way trail, featuring mixed terrain including trails, footpaths, tracks, and roads, with a total elev..

Fen Gallop 2026 is a scenic running event held in Willingham, Cambridgeshire, featuring flat, multi-terrain courses along country roads, footpaths, and bridleways. Participants can choose between a 10K race or a shorter 4-mile option, both offering chip timing. The event welcomes runners aged 15 and..

The Chiltern Ridge Half Marathon is a challenging 21.1 km trail race held in Buckinghamshire along The Ridgeway National Trail, between Wendover and Princes Risborough. Starting and finishing in Wendover, the course features an undulating forest loop through Whiteleaf Hill Nature Reserve, with over..

The Spitfire Scramble is a unique 24-hour multi-terrain relay or solo race held at Albyns Farm, London Borough of Havering. Participants can run solo or in teams of two to eight, tackling a 5.75-mile lap repeatedly through day and night. The course spans areas managed by Havering and Forestry Englan..

BigHeat Trails (FIRE) is the third event in the Classic Element Trail Series, held at Rother College in Midhurst, Surrey. Inspired by the element of fire, this trail running event offers two challenging single-lap distances: a marathon and a 16-mile run. The course features winding dusty tracks, sun..

The Great Barrow Challenge, hosted by Zig Zag Running, is a unique 10-day running event held at the Suffolk Running Centre in Bury St Edmunds. Participants can choose to run distances ranging from 5k and 10k to half marathon, full marathon, or ultra marathon, with the freedom to set their own pace...

The Maidenhead Trail Run, taking place 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 suitable for all levels, from beginners to seasoned t..

August 2026

The North Downs 50 Ultra Challenge is a premier endurance event held in the Surrey Hills, starting and finishing at Loseley Park, Guildford. Participants can choose from 50km, 25km, or 10km looped routes that showcase the scenic North Downs Way and surrounding countryside, offering varied terrain an..

The Black Bull 15 Trail Runs, held in Chelmsford, UK, is an annual charity trail running event featuring two distances: a competitive 15-mile trail run and a non-competitive 15km run/jog/walk. The course offers a scenic loop through local countryside and country roads, with opportunities to experien..

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),..

September 2026

The Henley River Half Marathon, 10k & Junior Race takes place at Temple Island Meadows, Remenham Lane, Henley-on-Thames, UK. Scheduled for September 5, 2026, this event features a half marathon, 10k, and a junior race for under-11s. The course offers fast, undulating mixed terrain trails alongside t..

October 2026

The South Downs 100 mile (Autumn Event) is a challenging single-loop trail race held in the scenic South Downs National Park, starting at Plumpton Racecourse in Lewes, East Sussex. Covering 100 miles with over 12,000 feet of elevation, the course features rolling hills and stunning views, supported..