Trail Running calendar near Winterbourne Monkton 2025-2026

Tackle 40 miles along the ancient Ridgeway from Avebury to Streatley on 9 May 2026, passing barrows, hill forts and the Uffington White Horse. Friendly checkpoints and great support make this a memorable long distance walk.

Challenge the Welsh Three Peaks: Snowdon, Cadair Idris and Pen y Fan across about 17 miles of rugged mountain scenery. Join guided events with transport and support or attempt a self organised challenge on public dates in 2026 and 2027.

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.

Shires and Spires on 10 May 2026 is a multi distance circular run from Naseby Village Hall across scenic trails and country roads past grand estates. Pick distances from 10K to an ultra and enjoy a memorable Northamptonshire running experie..

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..

Run scenic, hilly trails on the South Downs at the Cocking Trail Races near Midhurst, with 20 km and 10 km senior races plus 3 km and 5 km junior events. Chip timing, medals and refreshments make it a fun day for runners of all ages.

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.

Join the Dinton 5km and 10km Summer Series at scenic Dinton Pastures for four monthly, flat off road laps from May to August. Family friendly with a 2 km kids race, medals, water and post race treats including an ice cream van.

Take on the North Downs Way 50, a 50 mile point to point trail from Farnham to Knockholt Pound across rolling climbs and scenic countryside. Mostly trail with aid stations and a 13 hour cut off, it is a classic endurance challenge.

Explore the UNESCO Jurassic Coast on 16 17 May 2026 with options from 10 km to 100 km. Day and night or two day formats, strong on course support and spectacular coastal views make this a memorable challenge for runners and walkers.

Take on the OTT Trail Marathon or 10 mile race through the Brecon Beacons on 16 May 2026, featuring climbs over Pen Y Fan and sweeping reservoir views. A rugged looped trail challenge with scenic rewards and event buffs and coasters for fin..

Face the True Grit Trail Marathon on 16 May 2026 in Bridgend, a 26.2 mile adventure across mixed terrain, quarries and the notorious Mount Mayhem. Limited to 50 places, with a marked route, five aid stations and a bespoke finisher medal.

Take on the Compton Downland Challenge on 16 May 2026, choosing the marathon or a scenic 16 mile route across the Berkshire Downs and Ridgeway. Expect rolling trails, countryside views, on course aid and a hand thrown mug at the finish.

Join the Semington Slog on 16 May 2026 for a scenic 10K or family 2K around the village, canal towpath and leafy lanes. A friendly community fundraiser at St Georges School with marshalled routes, children’s activities and tasty food, plus..