Trail Running calendar near Maidenhead 2026-2027

A 24 hour off road trail event on *5 mile* loops offering Solo, Pair, and Team entries. The site includes camping, parking, caterers, and illuminated routes for night running.

A 13.5 mile single-loop trail through the South Downs National Park, starting and finishing at Helen Garden in Eastbourne. The route follows the South Downs Way via Friston Forest, Seven Sisters and Beachy Head with about 2,000 ft of ascent..

A Star Wars 50th Anniversary weekend on 5 and 6 June 2027 at Caldecotte, Milton Keynes featuring marathon and half marathon races around Caldecotte Lake, unique finisher medals, on-course water and toilets, and time limits for each race.

A 5k obstacle course at Royal Windsor Racecourse with mud obstacles to climb, crawl and slide, mixed tarmac and grass surfaces, staggered wave starts and a minimum age of 13. Earlybird entry prices and a fundraising target apply.

A 5 km obstacle course at Prospect Park in Reading where participants climb, crawl and slide across grassy slopes and woodland. Waves run every 15 minutes and the event is open to people aged 13 and over.

A 5k muddy obstacle course at Willen Lake with staggered wave starts, on-site toilets and parking, blue badge parking nearby, and a fundraising target of £50. The event is not wheelchair accessible.

An evening trail marathon on 5 June 2027 near Purleigh, Essex covering 27 miles with coastal, canal, vineyard and forest sections. The race has three checkpoints, mandatory lighting kit and cash prizes including a reward for a new course re..

Backyard Ultra at Chilton Manor Farm on 5 June 2027 features a 6706 m loop run each hour until one runner remains, with weekend camping, on route water stations, event camp facilities and medical support.

At Prospect Park in Reading this Race for Life event offers a 10k run as two laps of the 5k course plus a separate 5k option, with grass and woodland terrain and some steep slopes.

A multi-distance running event in Bath that passes through two long, lit former railway tunnels and starts and finishes at Brickfields Park. Options range from a 500 m Colourburst to an ultramarathon and the event supports Sustrans.

A mixed road and country run around Ousden in Suffolk offering 5k, 10k, half, full and ultra options with loop and out-and-back formats, regular aid stations, onsite parking and bespoke finisher medals.

Park-based 3k and 5k runs at Dunorlan Park with mixed grass and woodland terrain. The event is organised by Cancer Research UK and includes a fundraising pack and a finishers medal.

Trail running and cycling around Gosmore and Hitchin in the Chilterns AONB with 10 km, half marathon and marathon options, riders starting ahead of runners and a children’s event on the village green; some proceeds support charities.

A forest trail event at Wendover Woods offering a hilly multi-lap 10 km course with Half Marathon, 10k and Junior Run options, on-site facilities for spectators, route maps and GPX files, and medals plus free photos for participants.

A backyard ultra at Breakheart Quarry where runners repeat a **6706 metre** loop every hour until one person remains; the event includes camping, marked trails and on course support in the Cotswold countryside.

A multi-distance trail event around the Cotswolds from a Cirencester basecamp on 12 to 13 June 2027. Distances range from 10 km to 100 km with staffed rest stops, GPS tracking, camping, medical support and finisher kit.

Community 5k, 10k and junior races in Robertsbridge on a multi terrain, undulating course with volunteer marshals, a BBQ, post-race bar, bespoke medals and free parking.

Race to the King is a trail ultramarathon at West Dean Gardens on 19 June 2027, offering 30 km and 50 km loop options plus 80 km and 100 km non stop circuits across the South Downs Way and Monarchs Way with timed results and support.

The Race for Life Pretty Muddy Southampton will take place in Southampton on Saturday 19 June 2027. You can run 5 kilometers.

The Three Shires Way Ultra & Marathon will take place in Hanslope on Saturday 19 June 2027. You can run between 26 and 50 miles.