Trail Running calendar near Winchester 2025-2026

The Dorset Hillfort Ultra is a scenic 38-mile running event set in the picturesque West Dorset, featuring a challenging course with approximately 1,300 meters of ascent. Participants will traverse from one ancient hillfort to another, enjoying stunning views of Lyme Bay and the Jurassic Coast. The r..

Enigma Fireworks is a running event taking place on November 7th and 8th, 2025, at Caldecotte Lake in Milton Keynes. The event features both a marathon and a half marathon on each day, with participants completing scenic laps around the lake. Runners can expect a supportive environment with race bri..

The Druid's Challenge is an 83-mile (136 km) ultra marathon held over three days in November, traversing the historic Ridgeway in the UK. Participants experience stunning ancient landscapes, rolling chalk downland, woodlands, and notable monuments such as Stone Age barrows and Iron Age forts. The ev..

The South Downs Trail Run is a scenic off-road running event held in the South Downs National Park, starting from Goodwood Racecourse near Chichester, UK. Participants can choose from three distances: 21km, 19km, and 12km, catering to all abilities. The course features a mix of forest fire roads, br..

Big Night Out Winchester is an exciting night-time trail running event set in the scenic surroundings of Winchester, Hampshire. Participants can choose between a 22km or 12km course, both illuminated by headtorches as they navigate the trails and pathways. The event features a fully marked route wit..

Freedom Racing's 5 Trails Ultra & 3 Trails event takes place at Westerlands in Graffham, Petworth, within the scenic South Downs. The main Ultra is a stunning 50k loop that links five long-distance trails: the Serpent Trail, New Lipchis Way, West Sussex Literary Trail, Monarchs Way, and South Downs..

The Dirt Half Challenge is a popular half marathon trail race held in Leighton Buzzard, Bedfordshire. The course features a scenic and challenging route that includes an anti-clockwise lap of Tiddenfoot Waterside Park, a stretch along the picturesque Grand Union Canal towpath, climbs through beautif..

The Remembrance Day Run - South is held in Surrey, at the Wraysbury Skiff and Punting Club by the Riverside in Egham. This 7-hour time challenge allows participants to run a minimum of 5km, with laps of 7km (4.37 miles) along a scenic course beside the River Thames. The route is well-marked and feat..

The One by the Canal is a scenic half marathon trail run held in November, starting at Cowley Recreation Ground and finishing in Watford's Cassiobury Park. The course follows the Grand Union Canal, offering runners beautiful natural surroundings along country trails and woodland paths. The event fea..

The Bristol MoRun is a lively running event held at Ashton Court Park, featuring 1.5k, 5k, and 10k distances. The course combines paths and trails with hilly sections between 1km and 3km, suitable for dog walkers and off-road buggies but not wheelchairs. The 5k is a single lap, while the 10k covers..

The Southampton Half Marathon MoRun is a vibrant running event held at Southampton Common, featuring distances of 1.5k, 5k, 10k, and a half marathon. The course combines paths, trails, and grassy sections with an undulating terrain, suitable for dog walkers and buggy runners, though some parts may b..

The Maverick Exposure Lights Dark Castle is a unique trail running event held in Corfe Castle, Dorset, set against the dramatic backdrop of the historic Norman castle ruins. Scheduled for November 15, 2025, the race offers three distances: 15 km (long), 11 km (middle), and 5 km (short), with elevati..

The Bath Skyline running event, organized by Relish Running Races, offers 5km and 10km off-road races around the iconic Bath Skyline, featuring woodland trails, open meadows, and hilltop views of Bath. Held at the University of Bath's West Car Park, the course is mostly flat with some gentle rises,..

The New Forest Central Trail Run is a scenic trail running event held in the heart of the New Forest National Park, an Area of Outstanding Natural Beauty in the UK. Starting from Roundhill Campsite near Brockenhurst, the course features wide, hard-packed gravel paths weaving through ancient woodland..

The Centurion Wendover Woods 50 is a challenging 50-mile ultramarathon held entirely within Wendover Woods in South East England. The race consists of five 10-mile loops on forest trails featuring a mix of wide, soft paths with runnable climbs and descents, alongside steeper, more demanding sections..

The Rugged Radnage 10K Run, held in the Chiltern Hills near Radnage village, offers a challenging mixed-terrain course featuring roads, trails, footpaths, woods, and fields with notable ascents and descents. The event includes both 5K and 10K distances, with the 5K covering half of the 10K route. It..

Roly's Run is an annual trail running event held in the scenic Meon Valley and South Downs Way, Hampshire, in memory of ultra-runner Rich Walklate (Roly). The event offers three distance options: 15.5, 21.5, and 40 miles, featuring challenging ascents and approximately 80% trail terrain. The courses..

The Broadway Marathon is a challenging running event set in the picturesque northern Cotswolds, known for its hilly and muddy terrain. Licensed by the TRA and adhering to UK Athletics rules, the marathon is open to participants aged 18 and older. The event promises stunning scenery, making it a uniq..

The 5th Sundon Saunter is a walking and running event held in Barton-le-Clay, UK, on November 16, 2025. Participants can choose from three distances: 13 miles (walkers only), 18 miles, and 27 miles, passing through undulating countryside, woods, fields, tracks, and some roads, offering scenic views..

The Devil's Punchbowl 10k is a guided trail run held in the scenic Devil's Punchbowl, a natural amphitheatre located in Hindhead, Surrey. This 10km route features challenging hills and beautiful trails, offering runners spectacular views, especially during sunset or night runs. The event is designed..