Trail Running calendar near Winchester 2025-2026

The Rathfinny Run takes place at The Tasting Room, Rathfinny Wine Estate in Alfriston, Polegate (BN26 5TU) on 10 May 2026. The event is organised by 3WordRuns and is the third running of the race at this venue. There are two distance options: 10.7 km Half marathon (21.4 km) The event offers 30 fr..

The Compton Marathon & 16 Mile Challenge, part of the Compton Downland Challenge, is hosted by Compton Harriers Running Club in Compton, Berkshire. The event offers two routes: a marathon and a 16-mile challenge, both starting from the village recreation ground by the Village Hall (HQ). With a 7-hou..

The Jurassic Coast Ultra Challenge takes place on 16-17 May 2026 along the Jurassic Coast in Dorset. The route starts in Corfe Castle and finishes in Bridport, passing Swanage, Lulworth Cove, Durdle Door, Weymouth, Portland Bill, Chesil Beach and West Bay. Distances and route options include: 100..

North Downs Way 50 is a 50-mile point-to-point ultramarathon along the North Downs Way National Trail, from Farnham, Surrey to Knockholt Pound on the outskirts of Greater London. With about 5,600 feet of elevation gain, the mostly off-road route traverses iconic chalk downs, including Box Hill, and..

The Reigate Priory Park 10K is a scenic charity fun run held in Priory Park, Reigate, Surrey. The course features a 250-meter start plus four laps on an accurately measured, gently undulating cross-country terrain surrounded by lush greenery. Suitable for runners of all levels, the event fosters a f..

The London 2 Brighton Ultra Challenge takes place on 23-24 May 2026. It is a Capital-to-coast trail event with most routes starting in Richmond-upon-Thames and finishing at Brighton Racecourse. The full continuous route is approximately 100 km, crossing the North Downs, Surrey and Sussex countrysid..

RunThrough Trails presents The Fox, a quintessentially British trail running experience set in the picturesque Surrey countryside. On Saturday 23 May 2026, the event offers three distances: 20K, 41K, and 62K, with all routes finishing at Burys Field in Godalming. Courses launch from Burys Field, Wes..

Seven Sisters Half Marathon is a scenic, single-loop trail race through the South Downs National Park, starting and finishing at Helen Garden in Eastbourne. Runners follow the South Downs Way from Eastbourne to Friston Forest, traverse woodland trails, pass the Seven Sisters, and return over Beachy..

South Downs 50k is a 50 km point-to-point trail race from Falmer to Eastbourne, largely along the South Downs Way through the South Downs National Park and finishing over the Beachy Head cliffs. The route includes about 3,600 ft of ascent and descent, 99% runnable trail with some farm tracks and for..

Grand Union Canal Race (GUCR) is a 145-mile non-stop ultramarathon along the Grand Union Canal Towpath from Gas Street Basin, Birmingham to Little Venice, London. Dubbed “The Long Run” and regarded by many as Britain’s premier ultra, the race follows a way-marked, flat towpath through urban and rura..

The Ridgeway Challenge is an 86-mile (139 km) point-to-point trail running race along The Ridgeway National Trail. The race starts at Ivinghoe Beacon in Hertfordshire and finishes at Avebury in Wiltshire. The course has about 6060 ft (1850 m+) of elevation and a maximum of 250 runners. The minimum..

The Beat The Sunset 50km ultramarathon takes place on Saturday 30 May 2026 in Maidenhead, with the venue listed as Summerleaze Park, SL6 8SP. The race distance is 50 km on a single-lap course. The route is described as flat and multi terrain, using the Thames Path, Jubilee River and the Green Way...

The Circuit du Sore Legs is a unique running event held at Wodson Park Sports and Leisure Centre in Ware, Hertfordshire. Participants run on a traffic-free 400-meter athletics track, with distances ranging from 5k to a 6-hour challenge, including half marathon, full marathon, and 50k ultra options...

Surrey Hills Half Marathon is a guided trail half marathon based in Guildford, Surrey, covering about 13 miles. The route travels through the Surrey Hills, with highlights including St Martha's Church and hill, the village of Shere, and views from Newlands Corner and Hackhurst Downs, including secti..

BigSea Trails (WATER) is a trail running event held on the Isle of Purbeck, Dorset, starting and finishing on the sandy Knoll Beach at Studland. Part of the Classic Element Trail Series, this race celebrates the element of water with routes that showcase stunning coastal and countryside scenery, inc..

Two Tunnels Races in Bath, UK offer a unique city-centre running experience beneath the city via the Devonshire Tunnel (408m) and Combe Down Tunnel (1672m)—the longest underground section of any UK race. The well-lit, surfaced tunnels form a flat, shared-use path starting and finishing at Brickfield..

The Dell 10km is a multi-terrain running event held at Dummer Down Farm in Hampshire, hosted at the Dummer Down Brewery taproom. Distances offered: 10km Canicross 10km The route uses private farmland, trails, woodlands, fields and local roads. A finish-line cup and a free drink (alcoholic or non-..

Bewl Water Summer is Hermes Running’s bi-annual trail race at Bewl Water, near Lamberhurst, Kent. Runners start at the Bewl Water Visitor Centre and follow a clockwise circuit around the reservoir on undulating woodland trails and lanes, with lake views throughout. Distances include 10 km, half mara..

The South Downs Way 100 is a 100-mile non-stop ultramarathon along the South Downs Way National Trail, from near Winchester to Eastbourne, England. The course runs along chalk ridgeway with rolling hills, ancient forts, villages and coastal views, about 15% road and 85% trail. Runners are supported..

Centurion Running's South Downs Way 50km is a 50km trail ultra in the South Downs National Park. The race starts at Matterley Bowl near Winchester and finishes at Queen Elizabeth Country Park along South Downs Way. The course is 80% trail and 20% road, with about 4,000 ft of climb.The route features..