Trail Running calendar near Henley-on-Thames 2025-2026

We have found 376 Trailruns within 80 miles of Henley-on-Thames. See below where and when you can find the races.

Event overview The Essex AA Cross Country Relays will take place on Saturday 11 October 2025 at Hylands Park, Chelmsford, CM2 8FS. The event is hosted by Billericay Striders and follows the 2024 format for 2025. Race formats include: U13/1..

RunThrough Trails Beat Box Hill October 2025 The event takes place on Saturday 11 October 2025 at Box Hill Trail, Tadworth KT20 7LB (Event location: The Old Fort, Box Hill Road). The races are trail format with mapped courses for each dista..

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Event format This is a backyard ultramarathon in which participants run a repeated loop. Each loop is 4.167 miles (6.7 km). Runners must start each loop precisely on the hour and must complete the loop within that hour to continue. If a run..

Enjoy scenic autumn trails at Cowdray Estate with 5 km, 10 km and 10 mile routes through ancient woodland, deer park and technical descents. Canicross categories and festival vibes from the Farm Shop Apple Day add extra fun.

Event overview The Kent Downs 50 Challenge takes place on Saturday 11 October 2025 at Kent Showground, Maidstone. The event uses a basecamp near Maidstone with parking, weekend camping options, shuttle transfers to the nearest train station..

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The Barrows and Downs event, organized by And Over Trail Events, is a marathon and half marathon set in the historic southern Salisbury Plain in Wiltshire, England. Participants run among ancient barrows dating back to 3500 BC, enjoying sce..

Buckingham 10k is a charity running event in Buckingham Town Centre. The 10km multi-terrain route, organized by Run for the Sky, starts in the town centre and winds through Stowe Avenue, Stowe National Trust Gardens and farmland, offering a..

Event details The Southend Pier Marathon is a full marathon held on Southend Pier in Southend On Sea. The pier stretches for 1.34 miles. The event date is 12 October 2025. The race is organised by Sussex Trail Events. The minimum age for pa..

The Ridgeway Run is a challenging 15-kilometre (9.3 miles) trail race organized by Tring Running Club, featuring scenic routes mainly on footpaths and bridleways with stunning views of the Chilterns. The course starts near Tring, ascends th..

North Chilterns 50K - Event overview The North Chilterns 50K is a trail ultra held from Putteridge Bury Country House. The 4th edition takes place on Sunday 12th October 2025. The course distance is 50 km with approximately 798 m of elevati..

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Event The Titsey Trail 10k is an annual off-road race organised by Oxted Runners. The next edition is scheduled for Sunday 12 October 2025. The race distance is 10k. Entries are managed by Nice Work Race Management. The event is held under..

Event The Frieth Hilly 5km and 10km is scheduled for 12 October 2025 at Frieth Primary School, Frieth Hill, Henley-on-Thames RG9 6PR. The courses run in the Chiltern Hills between Marlow and Henley-on-Thames, about 35 miles from central Lon..

Event overview The South Downs Way Ultra Run is a guided 30-mile trail run that starts and finishes at Harting Down in West Sussex. The route follows sections of the South Downs Way and nearby trails, passing Beacon Hill, Cocking Down and K..

Event details The Marlow Donkey is a walking and running challenge held on 12 October 2025 in Marlow, Bucks. The event base is Liston Hall (Marlow Community Association), Chapel Street, Marlow, SL7 1DD. It is organised by LDWA - Thames Vall..

The ATW Holdenby House Trail & Canicross event takes place on the historic 2,000-acre Holdenby Estate in Northamptonshire, featuring a scenic 5.4 km traffic-free trail through estate grounds and surrounding farmland. Participants can choose..

Event overview The Tarmac Twister Trail takes place on 15 October 2025 and is organised by Essex Trail Events. The route is approximately 6 miles and the minimum age is 16. The event holds TRA permit 7706. It is a self-navigation trail race..

The Forest of Dean Ultra Marathon will take place in Coleford on Saturday 18 October 2025. You can run 34 miles.

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Autumn 100 : event overview The Autumn 100 is a 100 mile (approximately 161 km) continuous trail race held on 18 October 2025 from Goring & Streatley on the River Thames, Oxfordshire. The route is four out-and-back spurs of about 25 mil..

Gatliff Marathon : 18 October 2025 The Gatliff Marathon is an annual challenge walk, jog or run. The 2025 event is the 41st edition and takes place at Edenbridge Cricket Club, Matthew Cox Community Pavilion, Blossoms Park, Mill Hill, Edenbr..

Herstmonceux 8km Trail Race is a picturesque off-road loop around Herstmonceux, centred on Herstmonceux Village Hall (BN27 4JX). The 8km course winds through fields, bridleways and woodland with views toward the South Downs; distance is app..