Trail Running calendar near Bembridge 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.

Tackle the Chiltern Hills 100K on 9 May 2026, a scenic but demanding trail ultramarathon around Chesham with 1800m of climbing. Limited to 250 runners, the marked course features checkpoints, live tracking and a finisher medal.

Run to the Sea Brighton is a scenic 50km point to point ultramarathon from Horsham to Hove Lawns on the Brighton seafront. Enjoy trails, rolling downs and a coastal finish with feed stations and support for solo runners or two person relays..

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.

The Goring Gap Trails event, held in Mapledurham near Reading, offers a variety of running and walking challenges, including a 50-mile ultra, a 52K ultra, and a half marathon, alongside walking options of half marathon, full marathon, and a..

Take on a 40 mile Ridgeway walk across chalk downlands past hill forts, barrows and the White Horse. Limited to 250 places with checkpoints, support and a cloth badge for finishers.

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.

Take on the Midhurst Milers Cocking 10k, a hilly, scenic trail across the South Downs featuring steady climbs and a fast downhill finish. Limited online entries make this a must book for trail lovers chasing views and a rewarding run.

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.

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 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.

Run 50 mile point to point along the scenic North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb, mostly on trail. Enjoy stocked aid stations, race medical cover and a 13 hour cutoff for a true endurance challenge.

Run or walk the iconic Jurassic Coast in Dorset on 16 and 17 May 2026, from Corfe Castle to Bridport via Lulworth Cove, Durdle Door and Chesil Beach. Distances from 10 km to 100 km, with single day or two day options and Weymouth camping.

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.