Trail Running calendar near Winchester 2026-2027

A combined entry for four Centurion Running 50 mile events held between 10 April and 13 November 2027, with an entry fee of £480 and a minimum age of 20. Registration and payment are via SiEntries.

A 200 mile point to point trail race across South Wales from Chepstow to Worm’s Head, with a 120 hour limit, live runner tracking, eight aid stations and organised drop bag support.

A trail weekend at Cowdray Estate, West Sussex offering five distances from 12 km to 110 km, low technical difficulty, an event village with expo, and optional camping and race support.

City-centre trail event on 17 April 2027 with two route choices: a 55 km ultra and a 25 km trail run that use riverside paths, old railway sections, parks, and Leigh Wood Nature Reserve.

A 50K trail ultramarathon across the Chiltern Hills from Berkhamsted Castle to Hampden Meadow, routed via Ashridge, Ivinghoe Beacon, Coombe Hill and Whiteleaf Hill. Fully marked course, three checkpoints and a nine hour cutoff.

Windsor 50 is a supported trail event from Windsor Racecourse offering 50 km, 25 km and 10 km looped routes through the Great Park, past Windsor Castle and along the Thames Path, with rest stops, medical teams and GPS tracking.

Trail ultramarathons in the Mendip Hills offering two self navigation distances, 50 miles and 50 km, organised by Town and Country Harriers to benefit the Mendips Hills Fund. Aid stations, GPS trackers, finish medals, prizes and camping are..

A guided trail marathon of 42.2 km through the Chiltern Hills, including parts of the Ridgeway and Wendover Woods. English Athletics qualified leaders provide navigation and support, with refreshment stops and a wooden finisher's medal.

Three days of races across East Grinstead, Haywards Heath and Burgess Hill with 10 mile and 10k events, a chip timed mile, family fun runs and options for a combined full marathon or a virtual marathon.

Ibstone Circle on 18 April 2027 offers multi-terrain 5 km and 10 km routes through Wormsley Estate with a steep section called the Ibstone Kicker, plus a children s Run In Colour with 1 km and 2 km options.

A multi-distance canal and riverside ultraseries based at Streatley-on-Thames, featuring TR250, TR150 and TR100 with GPS tracking, checkpoint support and required navigation using provided GPX files and maps.

An inflatable obstacle course event in St Albans on 24 April 2027 offering 2.5k, 5k, 10k and 15k options with multiple inflatables, five music zones and a finisher medal. No timing and family friendly.

A walking and running event around Bath with routes of 12.5, 17, 21 and 26.5 miles over public footpaths, staffed checkpoints, a finisher's medal and post-event refreshments.

A blindfolded navigation challenge in Winchester where participants are dropped at unknown locations and must find their way back on foot. Options include 6 miles for visitors and 10 or 15 miles; no maps or GPS and a sealed emergency bag is..

A trail event at St Giles House offering races from junior fun runs to a marathon, virtual entries, camping and a dog option, while supporting the New Forest Marathon Community Fund.

An alternative to the London Marathon at Walton on Thames featuring a UKA certified 3.28 mile lap. Options include full and half marathon or a seven hour timed event, with a 150 mm finish medal for participants.

A Bronze Ticket backyard ultra on Portland where competitors run a 6,706 m loop each hour until one runner remains. The route offers coastal views, quarries and mixed surfaces, with on-site camping, chip timing and medic cover.

A five mile off road race through woods and farmland around Hurstbourne Tarrant in the North Wessex Downs. Organised entirely by volunteers since 2009, the annual event donates all proceeds to local charities.

A Pretty Muddy 5k obstacle course at Lydiard Park on 01 May 2027 featuring mixed paths, hills and muddy obstacles. The event has wave starts, blue badge parking on grass and a minimum fundraising target of £50.

A multi distance trek and trail event on the Isle of Wight with a 106 km full island route plus shorter options, supported by staffed rest stops, GPS tracking, medical teams, camping and shuttle transfers.