Trail Running calendar near Winchester 2025-2026

BigWayRound Winchester is a scenic trail run around the Itchen, St Catherine's Hill and the South Downs, offering 14 mile to 50K distances. Timed chip results, fully marked course and a bespoke medal or choose a tree planting instead.

Run through the rolling trails of Harewood Forest in the Muddy Runners spring trail race near Andover. Choose a 5k or 10k for a scenic, undulating course and mark 4 May 2026 in your calendar.

Take on the Chiltern Hills 100K, a scenic trail ultra across iconic Chiltern ridges and estates on 9 May 2026. Limited field and UTMB Index status mean a competitive, well supported race with challenging climbs, full marking and live tracki..

Run to the Sea Brighton on Saturday 9 May 2026 is a scenic point to point 50k from Horsham to Hove Lawns, crossing trails, rolling downs and the coastal promenade. Enter by 25 April; solo and 2 runner relay options with on course support.

Run scenic off road trails through Collingbourne woods at the Collingbourne Races, with half marathon and 10 km options. Chip timed event with medals and prizes for a memorable trail day.

Experience a scenic 50 mile point to point ultra from Taunton to Minehead, starting on flat canal towpaths then rolling coastal trails past marshes, beaches and woodland. Enjoy aid stations, a medal and stunning Westcountry views.

Westcountry Ultra 100 is a scenic and tough 100 mile trail from Taunton to Minehead, following canals, rivers and coastal paths. Expect dramatic views, challenging climbs and a 32 hour cutoff with plentiful aid stations.

Discover Goring Gap Trails near Reading in early May 2026, offering scenic trail challenges from a 6 mile walk with a river boat crossing to 52K and 50 mile ultras. Multi day camping adds a relaxed festival vibe for runners and walkers alik..

Tackle a scenic 40 mile Ridgeway walk or run from Avebury to Streatley, crossing the rolling chalk downlands of Wiltshire, Oxfordshire and Berkshire. Limited to 250 entrants, this classic May event blends challenge with stunning countryside..

Run beside the Thames at Runnymede for the Magna Carta Summer with 10 km, half and full marathon options that pass historic riverside landmarks. All finishers receive a bespoke Magna Carta medal.

Run through the scenic Rathfinny Wine Estate in East Sussex on 10 May 2026 with 10.7 km or 21.4 km loop options. Enjoy off road trails, recycled slate medals and a carbon neutral, cup less event raising funds for the WOLO Foundation.

Run the 13 mile Greenway Challenge in Letchworth Garden City on 10 May 2026, a self guided loop from Standalone Farm along the scenic Garden City Greenway. Receive maps and GPX, enjoy cake and a wooden finisher medal while supporting GRIT c..

Tackle a scenic 10 km trail across the South Downs from Cadence Cycle Club Café in Cocking, featuring rolling hills and a downhill finish. Junior races for ages 6 to 15, chip timing, medals and a lively race village make it a great day out.

Run through the Dorset landscape that inspired Thomas Hardy with a challenging trail half marathon or a 5 mile option. Start and finish at Dorchester Rugby Club with on route entertainment and an event village raising funds for local causes..

Join the Dilton Dash at Dilton Marsh for a scenic multi terrain 10K, 3K and half kilometre fun run, with medals for all finishers and prizes for top runners. Friendly small field event with refreshments and water stations.

Challenge yourself at the Chilterns 30, a 30 km trail across scenic Chiltern Hills with rolling woodland trails, ridgelines and village paths. Guided groups, well stocked checkpoints and a finisher medal with a Trees not Tees certificate ma..

Join the Scorpion Run on 10 May 2026 at Symonds Yat Rock for a scenic 10k trail through the Forest of Dean and Wye Valley with riverside views. Expect gravel tracks and a tough final 1 km climb to the cafe finish with coffee and hot food.

Join Black to the Trails at Dunstable Downs and Whipsnade for a welcoming day of trail running with 1K, 5K, 10K and Scotch Bonnet 10K options. Celebrate diversity with music, food, family fun and finishers medals on scenic chalk downland.

Join Hairy Legs on 10 May for a rugged cross country across two undulating woodland laps with a few final field challenges. Every entrant gets a t shirt, a free beer or soft drink, a post race BBQ and a prize for best dressed.

Enjoy a scenic one lap 10k through bluebell woods, undulating hills and open common in Surrey at Hampton Estate and Puttenham Common. Chip timed with bespoke 2026 medals, a friendly finish village and superb views.