Trail Running calendar near Ventnor 2025-2026

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.

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 on 10 May 2026 at Dilton Marsh for scenic multi terrain 10K, 3K and 1/2K fun runs supporting village causes. Expect stiles and gates, medals for all finishers and prizes for winners.

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 a classic 50 mile point to point ultramarathon along the North Downs Way from Farnham to Knockholt Pound, with rolling chalk ridge trails, the climb of Box Hill and about 1,700 m of ascent. Scenic, mostly trail and a true endurance..

Run the iconic Jurassic Coast from Corfe Castle to Bridport, passing Durdle Door, Lulworth Cove and Weymouth. Choose distances from 10 km to 100 km and tackle a one or two day challenge with full support and a finishers medal.

Take on the Compton Downland Challenge on 16 May 2026, choosing a scenic 26.8 mile marathon or a 16 mile route around the Berkshire Downs and ancient Ridgeway. Expect varied, sometimes muddy trails, great aid stations and a hand thrown mug..

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..

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

Join the Reigate Priory Park 10K on 17 May 2026 for a scenic cross country four lap route in Surrey. Enjoy a friendly race atmosphere, bespoke medals and the chance to support the charity Sport In Mind.

Run the scenic loop at Hurtwood Park Polo Club in Cranleigh, Surrey with distances from 5 km to ultra on mostly flat off road trails. Multi lap format and a seven hour time limit suit all paces and every finisher gets a memento.

The South Downs 50 km runs along the South Downs Way from Falmer to Eastbourne, finishing on the white cliffs at Beachy Head. Mostly runnable trails and 3,500 feet of climb make this a scenic coastal challenge for trail runners.

Take on the London to Brighton Ultra, a 100 km route from Richmond to Brighton with about 1500 m of ascent and a two day daylight option with an overnight midpoint. Fully supported with covered rest stops, medical teams, transfers and a fin..

The Fox invites trail runners to Surrey on 23 May 2026 with 20K, 41K and 62K routes starting from local villages. Courses are well marked with regular aid stations and a shared finish in Godalming.

Tackle the stunning Seven Sisters Half Marathon on the South Downs, a 13.5 mile single loop that crests the iconic cliffs, crosses Beachy Head and winds through Friston Forest. Expect rolling hills, mostly runnable trail and unforgettable c..