Trail Running calendar near Winchester 2025-2026

The Chiltern Ridge Classic 50K is an ultra trail race in the Chiltern Hills. The next edition is on 18th April 2026. The nominal distance is 50K, though the current route measures about 51 km with approximately 996 m+ of elevation due to HS2 road and footpath closures. The race follows sections of..

The event is a Half Marathon held in Seaford, East Sussex, with the next scheduled race on 19/04/2026. The route combines the Seaford seafront with sections on the South Downs and is described as a trail course with undulating terrain. Registration, number collection and bag storage are based at Se..

The Thames Ring 250 is a challenging 250-mile (approximately 256 miles) trail ultramarathon starting and finishing in Streatley-on-Thames, UK. The race follows an anti-clockwise loop along the Thames, the Grand Union Canal, and the Oxford Canal, primarily on flat canal and riverside paths. Despite t..

The Bath Beat is a walking and running event held on the southeastern edge of Bath, England, offering distances of 12.5, 17, 21, and 26.5 miles. The course traverses the scenic countryside of the southern Cotswolds, including woods, hills, river valleys, farmland, and a historic disused canal. Parti..

Butcombe Trail Ultra is a pair of self-navigation ultramarathons, 50 miles and 50 kilometres, set around the Mendip Hills in Somerset, England. The official Butcombe Trail is a 47-mile loop around six pubs in the Mendips, largely off-road, offering sweeping views and varied running country as it cro..

The Drop - Winchester is a unique and challenging race held in Winchester, UK, offering participants a choice between 10-mile and 15-mile distances, either solo or in teams. Inspired by military-style navigation, the event requires runners to find their way back to the event center from an undisclos..

The Ale Trail 15 mile run is a pub-led trail race in Alfriston, East Sussex, starting from the Ye Olde Smugglers Inne beer garden. The 15-mile course has a 4hr30min cut-off and pub checkpoints at The Hampden Arms and The Ram Inn, where runners log arrival and receive a beer token and snacks before c..

The Chase Trail Run 2026 is part of the Garmin UK Trail Running Festival on 26th April 2026. The event takes place at St Giles House, Wimborne St Giles, BH21 5NA and is organised by ORA Events Limited. Entries close on 22nd April 2026. A camping option is available for three nights (24th/25th/26th..

The Portland Pig Backyard Ultra is an ultramarathon event held at Grove Farm Estate, Portland, Dorset. In this unique race format, participants run a 4.167-mile (6,706 meters) loop every hour, starting on the hour, continuing until only one runner remains. The course offers diverse terrain including..

Saturn’s Midweek Chasing Numbers 7-Hour Time Challenge is held at Wraysbury Skiff & Punting Club on the River Thames. The event is designed to be affordable and flexible, inviting all abilities to run or walk within a 7-hour window. Participants choose their distance on a flat, signed course along r..

The Isle of Wight Ultra Challenge is a coastal-footpath event on the Isle of Wight, starting at Chale Basecamp. In 2026, it offers multiple distances: a full continuous 106 km around the island (clockwise), a 52–54 km two-day option, plus 82 km, 50 km Southern Loop, 25 km Quarter, and a Medina 10-mi..

Thames Path 100® is a 100-mile point-to-point trail race by Centurion Running, from Richmond in London to the grounds of Oxford University. The route follows the Thames Path with a flat, fast profile on groomed paths, trails and paved sections, and about 1,900 feet (560 m) of climb, offering varied..

The Greensand Way Ultra Run is a guided, group trail run taking place on Saturday 2 May 2026 in Guildford, Surrey. The route covers 30 miles and the advertised cost is £45 per person. The event is presented as suitable for first-time ultra runners; participants are advised to have run at least 22 m..

Box Hill Vertical KM is a guided trail run held around Box Hill near Dorking, Surrey. The course covers about 12.5 miles with around 1000m of elevation, designed to rack up significant height in a compact distance. It traverses woodland, heathland and open fields, with hills that are technical enoug..

Rapid Relays is a dynamic running event held at the scenic Culden Faw Estate in Fawley, near Henley on Thames, Oxfordshire. The race features a woodland trail course on estate tracks with gently undulating terrain, including a notable climb before 3 kilometers followed by a long downhill stretch bac..

Tempo Trail Races returns for a weekend of trail running in the Cotswolds, centered at Ilmington Sports & Social Club, Ilmington, Shipston-on-Stour. The event offers multiple distances: a 100km Ultra, a new 50km Ultra, Marathon, Half Marathon, and 10K. The trail course takes runners through rural co..

Three Forts Challenge is a trail-running event based at Lancing Manor Leisure Centre in West Sussex. It offers three races: a Full Marathon (27.2 miles) starting and finishing at Lancing Manor, with steep climbs, stiles and rough tracks, passing Chanctonbury Ring and Cissbury Ring for panoramic coun..

The Bluebell Bash is a trail running event in Manswood, Wimborne, UK, organized by Tri-Counties Trail Running. It offers three distances—half marathon (13.1 miles), 10K, and 5K—with full accessibility for canicross. Runners traverse scenic bluebell forests with gentle hills and expansive views.The e..

BigWayRound - Winchester is an award-winning, Gold-rated trail running event held at Winchester Rugby Club. The event offers four distances: 14 miles, 19 miles, a marathon, and a 50K ultramarathon, catering to both new and experienced trail runners. The course features stunning views and traverses i..

The Harewood Forest Trail Race is staged in Harewood Forest in the heart of the Test Valley, near Andover, Hampshire. Runners can choose between 5k and 10k trail routes on undulating forest tracks, offering a challenging yet scenic course. Described as a spring race set in a beautiful woodland setti..