Trail Running calendar near Winchester 2026-2027

The Ridge Off Roader is a trail run through the scenic Chiltern Hills. It offers a half marathon and a 10k route, plus a fun 1k for kids. All proceeds support the local school.

Off-road multi lap run at Nutbourne Vineyards with views to the South Downs. Choose distances from 5 km up to a half marathon on the day; entry is £29, places are limited to 100, and finishers receive a medal, drink and cake.

An off road 10 km trail around Barbury Castle near Wroughton, featuring tracks, grass and Smeathes Ridge. The event is fully marshalled, supports Wiltshire and Bath Air Ambulance Charity and includes a finishers medal and post race refreshm..

Join the first race of the ELVIS 2026 series in Dagenham. This five mile multi terrain event features a three lap course through the scenic Eastbrookend Country Park with on site facilities and chip timing.

This 50 km point to point trail race follows the South Downs Way from Falmer to Eastbourne. Experience a scenic route through the National Park finishing over the iconic white cliffs of Beachy Head.

A multi distance trail event from Richmond upon Thames to Brighton Racecourse on 23 and 24 May 2026. Distances range from 10 km to a continuous 100 km with staffed rest stops, GPS tracking, medical support and camping options.

A point-to-point trail run in Surrey on 23 May 2026 offering 62K, 41K and 20K routes plus two and three leg relays. All races finish in Godalming with food, music and chip timed results.

Experience a scenic 13.5 mile trail loop through the South Downs National Park including the coastal Seven Sisters and Beachy Head. This runnable course features 2,000 feet of elevation with professional timing and support.

A 100 mile LDWA walk across Kent and Sussex over the Spring Bank Holiday weekend, visiting Ashdown Forest and sites linked to Winnie the Pooh. Entrants must be LDWA members, meet a qualifier and follow event rules.

Experience the twilight beauty of Ardingly Reservoir during this sunset run in West Sussex. Choose between a 5km or 10km distance on a scenic undulating trail and enjoy a timed midsummer evening event with finishers medals.

A Backyard Ultra at the Lower Red Lion where runners complete a 4.167 mile loop every hour until one remains. Individual entries only, limited to 90, with part of the entry fee donated to local charity Youth Talk.

A three-lap 26.2 mile marathon through Richmond Park, starting and finishing near Sheen Gate. The route uses the Tamsin Trail for two laps, features chip timing, drink stations and marshals, and has a 6 hour 30 minute cutoff.

A trail event in Ealing, London on 24 May 2026 offering Trail 25K and Ultra 50K distances. Routes run on mixed off-road terrain through parks and towpaths and include chip timing, aid stations and route files for entrants.

A trail running event in Taunton on 24 May 2026 with a flat, fast riverside route offered over 10K and Half Marathon distances. Organised by Prosper Events, it features top three awards by gender and a large finisher medal for all participa..

Point to point ultramarathon across Dorset offering 100k, 50k and an 18 miles Purbeck Traverse. The mostly off road route uses marked GPX tracks, includes steep Purbeck ridges and coastal views, and requires mandatory kit and prior marathon..

Run a flexible distance along Winchester's scenic Itchen Way. Choose your laps from 2.62 miles up to an ultra within a 7-hour window, with a famous aid station and a finisher's medal for all.

A chip timed *10k* trail run on 24 May 2026 that starts and finishes at Bredon Cricket Club. The marshalled route climbs to the 299 m summit of Bredon Hill and all finishers receive a medal.

A 10 km multi-terrain trail run at Marlow Rugby Club featuring local trails, woodland and Thames towpath. Entries include timing, a medal, a pint cup with a free drink, and basic on-course support; minimum age 16 and a two hour cut off.

An off-road race in Dursley on 25 May 2026 covering about 10.31 km with 318 m of climb, visiting Cam Peak, Cam Long Down, Uley Bury and Downham Hill. Entries are limited to 120 and handled via Entry Central.

A timed Friday event on a flat 5.3 km out-and-back course along the river Thames, with lap-based distances from 5 km to ultra and a £10 Run for a Tenner entry benefiting Rays of Sunshine.