Trail Running calendar near Winchester 2026-2027

Black to the Trails is a vibrant trail running festival designed to boost ethnic diversity in the sport. Run a 1K, 5K, 10K, or Scotch Bonnet 10K on the beautiful trails of Dunstable Downs. Enjoy a day full of activities, food, and music wit..

The Woodland Woggle is a scenic 6k trail race through Hampton Estate and Puttenham Common. Expect undulating hills, Bluebell woods, and chip timing, with a bespoke medal for every finisher. Ample parking and refreshments are available at th..

A series of marked trail races around Stroud and the Cotswolds using towpaths, commons and old railway lines, with checkpoints, water stations, marshals and map/GPX support.

Celebrate summer with this flat, off-road race series in Dinton Pastures Country Park. Choose from 5km, 10km, or a kids' 2km across four Thursday evenings. Enjoy chip timing, a finisher's medal, and a friendly atmosphere.

Event Overview The North Downs Way 50 (NDW50) is a 50-mile point-to-point trail run along the North Downs Way National Trail. It starts in Farnham, Surrey and finishes in Knockholt Pound, on the outskirts of Greater London. The total climb..

A multi-distance trek and trail event along the Jurassic Coast from Corfe Castle to Bridport on 16 and 17 May 2026. Distances range from 10 km to about 100 km with camping, transfers, GPS tracking, medical support and catered rest stops.

Compton Harriers stage the Compton Downland Challenge on 16 May 2026 with a multi-terrain full marathon (26.8 miles) and a 16 mile route across the Berkshire Downs. The event includes aid stations, a seven hour limit and a hand-thrown finis..

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.

The Maverick Cotswolds Trail returns for its 11th year on May 16, 2026. Starting from the historic Sudeley Castle, runners can choose from five scenic trail distances, from a 7km Short to a 51km Ultra. This dog-friendly event features a cup..

A measured 10 km cross country run in Priory Park, Reigate on 17 May 2026 with a 250 metre section plus four laps, water stations, first aid and registration on the day. Trophies and a bespoke medal are awarded and the event supports Sport..

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.

A community running event in the parish of Deddington offering 5k, 10k and 20k routes on Sunday 17 May 2026. The event is open to all and supports local organisations including the Deddington Primary School PTA, Deddington PFSU and Deddingt..

This 10K trail race starts and finishes on Cocklemoor in Langport, taking runners across mixed terrain paths through the Somerset Levels and countryside. It follows UK Athletics rules and is open to participants aged 17 and over.

A community trail run on 17 May 2026 at Newchurch Primary School with three route options and age-based entry fees; proceeds support learning resources and all entrants receive a medal and enter a raffle for prizes.

Join the Barbury Castle Sunset 10km for an evening trail run through the Wiltshire countryside. The off-road route passes historic Barbury Castle and finishes with refreshments at the shooting school. All profits support the Wiltshire and B..

Four point to point races across the South Downs National Park on 23 May 2026, with mainly runnable, non-technical trails and a finish at Beachy Head in Eastbourne. Courses are fully marked and supported with regular aid stations.

A multi-distance trail event from Richmond upon Thames to Brighton on 23 to 24 May 2026. Distances include 100 km, 50 km, 25 km and 10 km with marquee rest stops, medical support, GPS tracking and optional camping.

A Surrey trail running event on 23 May 2026 offering 20K, 41K and 62K routes that all finish at Burys Field, Godalming, with marked courses, regular aid stations and an 11 hour cutoff policy.

A single loop trail race in the South Downs National Park starting and finishing in Eastbourne. The 13.5 mile course follows the South Downs Way via Friston Forest, the Seven Sisters and Beachy Head with 2,000 feet of elevation.