Trail Running calendar near Isle of Wight 2026-2027

We have found 433 Trailruns within 80 miles of Isle of Wight. See below where and when you can find the races.

A 40 or 50 mile trail ultra along the Testway from Linkenholt to Totton in Southampton, with aid stations every 10 miles, marshals and medical support. A shuttle option is available for an extra £10 and there is a 14 hour cutoff.

Trail running at Stanmer Park on 3 April 2027 with three waymarked routes : 5 km, 13 km and 21 km : across South Downs Way terrain, on-course outposts, timing and support.

A 42km off road marathon from Stanmer Park across the South Downs to a finish on Hove Lawns. The route includes Ditchling Beacon and joins the Brighton Marathon for the final 6km.

Scenic mixed terrain races along the Thames at Remenham Farm in Henley on Thames. Options include a Half Marathon, a 10K and a Junior Race with marked trails, marshals, chip timing and post race goodies.

A 50 mile point-to-point race along the South Downs Way from Worthing to Eastbourne, featuring about 5,700 ft of climb, seven staffed aid stations, mandatory kit checks and a 13 hour finish limit.

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 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.

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..

Three town races across a Bank Holiday weekend in West Sussex offering 10 mile, 10k, mile and fun runs plus marathon and triple mile combos. A virtual marathon runs between 17 April and 3 May 2027.

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.

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.

May 2027

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.

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