Trail Running calendar near Winchester 2025-2026

We have found 388 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

Join the Eggcellent Easter Pink Run in Egham for a friendly seven hour timed challenge along the Thames where runners and walkers choose how far to go. Enjoy riverside trails, an Easter egg medal and a tasty goody bag at the finish.

Run the Testway Ultra on 4 April 2026 and choose a scenic 40 or 50 mile route along Hampshire's Testway with regular aid stations and a 14 hour cutoff. Medals and prizes await finishers.

Take on the Unbreakable Treasure Run on 5 April 2026 at Xcel SPORTS HUB, Walton on Thames, running timed laps along a flat riverside towpath from 5 km to ultra. Limited places and a 7 hour time cap make this a focused challenge with a keeps..

Take on the Mortimer 10km through scenic Berkshire woodlands on Monday 6 April 2026. This undulating two lap off road course features chip timing, medals and a dog friendly canicross start for runners with dogs.

Take on West Wight 3 Hills, an undulating 8 mile coastal loop from Freshwater that climbs Tennyson Down and Alum Bay. Organised by Ryde Harriers, it is scenic, testing and gives every finisher a souvenir.

Enjoy a scenic 5 mile loop around Hall Barn Estate with a tarmac start and finish at Beaconsfield Rugby Club. Organised by Burnham Joggers on 6 April 2026, this friendly trail run features marshals, chip timing and post race prizes.

Take on the 50 Mile Grand Slam 2026 from Centurion Running and complete four epic 50 mile trail races across the UK. A true year long challenge for experienced runners seeking big miles, camaraderie and stunning scenery.

Run 50 miles along iconic chalk ridges from Worthing to a lap on Eastbourne athletics track, with rugged climbs, sweeping coastal views and a festival finish. This tough but rewarding ultra kicks off the 2026 50 Mile Grand Slam.

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Take on the Henley River Half Marathon, 10K or Junior Race in Henley on Thames on 11 April 2026, with options for all ages including a kids race. Enjoy mixed terrain, riverside views, medals, free photos and a buzzing event village.

Spring Run the Seasons Cowdray on April 11 offers scenic trail races across Cowdray Estate and the South Downs, with distances for kids, juniors and adults plus dog friendly CaniRun options. Enjoy varied trails and country views for all abi..

Tackle scenic chalky trails around the South Downs and Ditchling Beacon at the Maverick East Sussex Trail in Stanmer Park. Choose from 21 km, 13 km or 5 km routes with rolling hills, great views and a lively community atmosphere.

Run a guided Chilterns Trail Marathon along the Ridgeway and through Wendover Woods, featuring rolling hills and expert leaders offering pacing and technique tips. Small field, halfway refreshments and a wooden finisher medal make for a sce..

The Big Cheese is an off road fell race in Cheddar, Somerset, covering 15 miles across the Mendip Hills with over 2,000 ft of climb. Take on a fully marked course and enjoy a finisher's medal plus tea and cake at the end.

Take on the 42 km Brighton Trail Marathon through the South Downs from Stanmer Park to Hove Lawns on 12 April 2026. Hilly chalk ridgelines, woodland and a finish on the Brighton Marathon route promise a scenic, rewarding challenge.

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Take on the Wild Horse 200 series: two epic 200 mile trail ultramarathons across Welsh trails and mountains. Run the South Wales coast route from Chepstow to Worm's Head in April or the Mid Wales loop from and to Machyntlleth in June.

Run scenic loops from Windsor Racecourse through Windsor Great Park, Runnymede and the Thames Path with views of Windsor Castle. Choose 50 km, 25 km or 10 km loops with aid stations, timing, a finisher T shirt and medal.

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Take on the Chiltern Ridge Classic 50K, a 51K trail ultra across the iconic Chiltern Hills with 996 m of climbing, starting at Berkhamsted Castle and finishing in Wendover. Expect Ridgeway views, tough trails and full on course support.

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Run the Spring Trail Series at Cowdray Estate where the Serpent Trail winds through greensand hills, rivers and woodland. Distances from 12 km to 110 km, with food, camping and relaxed cutoffs for a friendly, well supported day.

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Tough but rewarding 10 km fell race around Chingford with 450 m of climbing, hosting the first ever Essex County Championships. Pre entry only and open to Essex eligible runners aged 16 and over, with teams welcome.

Run the Martello Half Marathon in Seaford along seafront and South Downs trails, a scenic but undulating course with marshal support. Enjoy great views, a bespoke medal and free photos while backing local charities.