Trail Running calendar near Winchester 2026-2027

We have found 499 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

An off-road charity event in Findon with a 10km trail, a 10km CaniRun, a 5 mile course and a 2km kids run around Nepcote Green. Proceeds support Findon Swimming Pool and the local school PTA.

Timed lap event at Buchan Country Park on 19 April 2026 with 5.3 km laps to create distances from 5 km up to ultra within a 7 hour limit. Runners may choose one of twelve medals or a lower cost no medal entry.

Experience a timed run through the Chiltern countryside and the exclusive Wormsley Estate. This event offers mixed terrain courses over multiple distances starting from Ibstone Common to support a local primary school.

A multi-distance riverside series based at Streatley with 250, 150 and 100 mile options. Runners navigate with provided maps and GPX, use GPS tracking and reach checkpoints under strict cutoff times while carrying compulsory safety kit.

Explore the scenic Cotswold countryside south of Bath with this supported trail event featuring four routes ranging from 12.5 to 26.5 miles for both walkers and runners.

Self navigated ultramarathons across the Mendip Hills AONB from Mendip Activity Centre, with 50 miles and 50 kilometres routes that qualify as UTMB index races. Organized by volunteer Town and Country Harriers to support the Mendip Hills Fu..

An inflatable 5K obstacle course in St Albans on Saturday 25 April 2026, featuring a series of inflatable obstacles along a 5K route; recent booking figures and participant feedback indicate active interest.

A multi terrain seven mile race at Kilmington Cricket Ground on 25 April 2026, with a 4 km option and a 1 km fun run for children. The undulating route passes roads, woodland and fields and offers on-site refreshments and a water station.

Run your own marathon on The Itchen Way in Winchester. This flexible 7-hour event lets you decide your distance on the day, from a short lap to an ultra, with medals for all finishers. Start any time before 1 PM and enjoy a stocked aid stat..

A community 10 km race in the Frome Valley starting and finishing at Elm Park Primary School in Winterbourne, with a varied terrain course on road and trails. Proceeds support Elm Park Primary School.

A 15 mile trail run from the beer garden of the Ye Olde Smugglers Inne in Alfriston with two pub checkpoints offering a drink and snack; route GPX and a race narrative are provided and results appear within 24 hours.

Experience a diverse range of multi terrain races including a full marathon half marathon and 10K. This festival offers distances for all levels plus dog friendly runs and a vibrant colour fun run.

A blindfolded navigation challenge from an event centre in Winchester where participants are taken to an unknown location and must find their own way back on foot. Options include a non local 6 mile challenge and 10 or 15 mile routes measur..

Trail runs through Angmering Park Estate in Patching on 26 April 2026, with 10-mile and 10 km courses amid bluebells. Canicross entries are available for a small supplement and the finish is at The Worlds End Pub.

Bolt Round the Holt is a forest trail race at Alice Holt Forest on 26 April 2026 offering Half Marathon, 10k, 5k and a Junior Run while raising funds for GUTS to support bowel cancer detection and care.

Join NOT the London Marathon Run 2026 on Sunday 26 April in Walton on Thames for a flat, certified lap course along the riverside towpath. Choose marathon, half or a 7 hour timed challenge, enjoy flexible starts and a commemorative medal.

A guided 10 km trail run through bluebell carpeted woods in the Chiltern Hills, meeting in Tring. Groups are led by Run Leaders who offer trail running tips; facilities include a nearby cafe, toilets and bag drop.

Trail event in the South Downs offering 28 miles and 18 miles routes with 4000 plus ft or 2800 plus ft ascent. Routes pass Seven Sisters, Cuckmere Haven and downland villages and are open to walkers and runners.

A circular walk from Pewsey Scout Hut across the Vale of Pewsey to the Marlborough Downs with routes from 10 mile to 35 mile, checkpoint refreshments, site visits and an e certificate for finishers.

May 2026

A Silver Ticket backyard ultra at Grove Farm Estate on 1 May 2026 where competitors run repeated 4.167 mile loops each hour until one runner remains. Entry includes on-site camping for the runner and two crew.

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