Trail Running calendar near Winchester 2025-2026

We have found 294 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

The Humanity Direct Amersham Ultra is a one-day endurance event held in the scenic Chiltern Hills, starting and finishing at Dr Challoner's Grammar School in Amersham, Buckinghamshire. Participants can choose from three distances: 10km, 25km (half ultra), or the full 50km ultra marathon, with ascent..

The Gratitude 25km is an exciting running event taking place in Broxbourne, UK. This race is designed for runners of all levels, promoting fitness and community spirit. Participants will enjoy a scenic route while challenging themselves to complete the 25km distance. The event emphasizes the importa..

Winter's End - 50 Mile Ultra & Marathon is a scenic trail running event held along the South Downs Way National Trail, starting near Arundel, West Sussex, and finishing in Winchester, Hampshire. The event features a 50-mile ultramarathon and two marathon options covering either the first or second h..

The Windsor Trail Run March 2026, hosted by RunThrough UK, takes place on March 22, 2026, at Alexandra Gardens in Windsor, UK. This event offers two race distances: a 10K and a Half Marathon, both featuring flat, trail terrain with scenic views of Windsor Castle. The 10K has an elevation of 29 meter..

The Forest of Dean Spring Trails Half Marathon is a scenic 13.1-mile race held annually in the Forest of Dean, starting and finishing near the Speech House Hotel. The course features well-maintained woodland trails with gentle inclines, offering a multi-terrain experience through beautiful forest la..

The Elephant Challenge by Big Bear Events is a unique 6-hour running event held at Salcey Forest, near Northampton, England. Participants run multiple laps of a 3.5-mile off-road loop through well-maintained forest paths, with terrain consisting mainly of crushed stone and forest floor, offering a n..

The Bath 50 Ultra Challenge is a premier trekking and trail running event held in the historic city of Bath, UK. Participants can choose from three looped distances: 50 km, 29 km, or 10 km, all starting and finishing at Bath Racecourse. The course offers scenic panoramic views, passing iconic landma..

The Run the Wild Half Marathon - Spring Edition is a 13-mile (21.1 km) trail running event set in the scenic Chiltern Hills, just 40 minutes northwest of London near Tring. Featuring rolling chalk hills and woodland paths with around 300m of ascent, the course offers a welcoming atmosphere for all a..

The Bristol Trail & Ultra, held on 28 March 2026, is a trail running event in Bristol offering two distances: a 25km trail and a 55km ultra. Both races start and finish at Museum Square in central Bristol, taking runners through scenic woodland, riverside paths, parks, and disused railway lines. The..

The Springtide 50k is an ultra running event held in the historic town of Arundel, West Sussex. This single-loop course offers a runnable, non-technical route through the scenic South Downs, making it ideal for beginners and experienced runners alike. Participants enjoy stunning views of rolling hil..

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The Minster Challenge 2026, held in Axminster, Devon, offers three running distances: 12km, 5km, and a 3km fun run suitable for all ages. Organized by Ruby Red Running in partnership with Axe Valley Academy, the event features a challenging course with hills and mud, promising an engaging trail runn..

April 2026

The Testway Ultra is a challenging ultra marathon held in Hampshire, England, featuring 40 and 50-mile distances along the scenic Testway footpath. The route stretches from the chalky downs near the Northern Hampshire/Berkshire border to the southern town of Totton in Southampton, showcasing picture..

The Mortimer 10km is a scenic trail running event held in the charming Berkshire village of Mortimer, starting and finishing at Mortimer Fairground. The race features a beautiful two-lap, multi-terrain course that covers woodland trails, footpaths, and bridleways with an elevation gain of 85 meters...

The Henley River Half Marathon, 10k & Junior Race takes place in April 2026 at Temple Island Meadows, Henley-on-Thames, UK. This scenic event features a mixed-terrain, undulating course along the Thames, starting and finishing at the iconic Royal Henley Rowing Regatta launch point. The half marathon..

The 50 Mile Grand Slam 2026, organized by Centurion Running, is a series of four challenging 50-mile ultramarathons held across iconic UK trails. The event includes the South Downs Way 50, North Downs Way 50, Chiltern Wonderland 50, and Wendover Woods 50, taking place between April and November 2026..

The Centurion South Downs Way 50® is a challenging 50-mile ultramarathon held annually in Southern England, starting in Worthing and finishing with a lap at Eastbourne Sports Club Athletics Track. The course follows the scenic South Downs Way National Trail, featuring 5,700 feet of elevation gain ov..

The Wild Horse South Wales 200 is an epic 200-mile ultramarathon traversing the scenic trails and mountains of South Wales. The course starts in Chepstow and finishes at Worm’s Head, following iconic routes such as Offa’s Dyke, the Beacons Way, the Heart of Wales Line, and the Wales Coast Path. This..

The Windsor 50 Ultra Challenge, formerly known as the Easter 50, is a premier UK trail running and trekking event held at Windsor Racecourse. Scheduled for April 18, 2026, it offers three looped distance options: a 50 km ultra, a historic 25 km, and a 10 km challenge. Participants traverse scenic ro..

The Spring Trail Series by Ultra X is a trail running event held at the Cowdray Estate in Surrey, within the scenic South Downs National Park. The series features five race distances: 12km, 25km, 50km, 50 miles, and 110km, all starting and finishing at the same accessible location near Cowdray Farm..

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The Chiltern Ridge Classic 50K is an iconic ultra marathon held in the Chiltern Hills, UK, featuring a challenging 51 km trail run with 996 meters of elevation gain. The race starts at historic Berkhamsted Castle and finishes at Hampden Meadow in Wendover, traversing stunning ridgeline trails betwee..

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