Trail Running calendar near Winchester 2026-2027

Enjoy a flexible 7 hour time challenge along the scenic River Thames in Egham. Run or walk as many laps as you choose to earn a medal and special distance pins at this inclusive midweek event.

A multi-distance trek and trail event on the Isle of Wight over 2–3 May 2026 featuring routes past the Needles, Cowes and Ventnor, full course support, camping and GPS tracking. Distances range from 10 miles up to about 106 km.

Experience a 100 mile point to point trail race following the iconic Thames Path from London to Oxford. This flat and fast course offers a 30 hour time limit through beautiful English riverside scenery and groomed trails.

Experience a guided 30 mile group run through the Surrey Hills featuring the North Downs Way and the Greensand Way. This non competitive ultra includes summits like Leith Hill and expert coaching throughout the journey.

A three day series across East Grinstead, Haywards Heath and Burgess Hill offering 10 mile, 10k, mile and fun run distances plus combined marathon and virtual options.

Run Silchester is an annual village trail event offering 2.5, 5 and 7 mile routes that pass a Roman wall, a 12th-century church and woodland. The event raises funds for the Silchester Sports Pavilion Charity and supports a local food pantry..

Experience the scenic trails and woodland paths of Hampstead Heath in this annual charity event featuring chip timed races and a community fun run with views of the London skyline.

Experience an off road five mile race through the picturesque North Wessex Downs. Follow woodland tracks and rural footpaths on a course starting in Hurstbourne Tarrant with all proceeds supporting local charities.

A single entry package for four Centurion Running 100 Mile events from May to October 2026, including Thames Path 100, South Downs Way 100, North Downs Way 100 and Autumn 100. The event listing shows the Grand Slam is full and the minimum a..

Experience a weekend of trail running in the Cotswolds with distances ranging from a 10K to a 100KM ultra marathon. Starting from Ilmington these UKA regulated races now include a new 50K option for all participants.

Trail races across the South Downs from Lancing Manor Leisure Centre on Sunday 3rd May 2026. Choices include marathon, half marathon and a 5 mile trail run with aid stations and course marshals.

Experience a guided group trail run through the Surrey Hills designed to reach 1000m of elevation. This non competitive 12.5 mile journey features technical climbs and woodland trails led by an experienced mountain leader.

Trail run through bluebell woods near Manswood, Wimborne offering Half Marathon, 10K and 5K distances. The event provides way-marked routes, aid stations, finisher medals and on-site facilities.

Run your own distance along the scenic Stroud Waterways canal in this flexible timed event. Start when you like within a one-hour window and see how far you can go in seven hours. Every participant gets a finisher's medal.

Experience the beauty of the North Wessex Downs with trail races of 20 or 33 miles. Run through historic sites like Avebury and the rolling Wiltshire countryside on courses designed for trail enthusiasts.

Enjoy a guided 5km trail run through the Chiltern Hills followed by a specialized movement class. This event includes expert run leaders, trail technique instruction, and basic facilities at Church Farm Cafe.

A friendly trail run on Headley Heath near Leatherhead with a two lap 10 km route through open and woodland paths. The undulating course has a small hill on each lap and offers scenic views and bluebells.

A trail festival in Winchester on 4 May 2026 offering four distances from 14 miles to a 50K ultramarathon, fully marked routes, aid stations and parking at Winchester Rugby Club.

Take on the Freddo Mercury Rhapsody Run along a flat riverside towpath at Xcel SPORTS HUB, logging as many 5.3 km laps as you can within a relaxed 7 hour limit. Rock up in a 1.5 hour start window or request a time, with aid stations and opt..

An annual off-road race day around Chepstow Park Woods starting and finishing at Hood Memorial Hall, Devauden. Distances include 10k, 5k, 2.4k for ages 8 plus and a 60m junior dash with a small donation on the day.