Trail Running calendar near Winchester 2026-2027

Winchester Trail Run in January 2027 offers two off road routes around Farley Mount near Winchester, including a half marathon and an Epic course with a short climb and countryside views.

A trail half marathon and 10K in Moors Valley Country Park, Dorset, run on gravel woodland paths with lap-based routes and limited canicross places. The event is chip timed, fully marked and follows several eco-friendly measures.

The May Hill Massacre is a demanding 7-8 mile cross-country run in Gloucestershire, featuring steep climbs and muddy trails. A longer 14-15 mile Mayhem option is available for those seeking an extra challenge.

Trail runs start and finish in Queen Elizabeth Country Park on the South Downs, passing through Head Down, the South Downs Way and the Milky Way. Three route lengths are offered and finishers receive a medal, a drink and event goodies.

A twilight out and back trail in Hurn Forest offering 5 mile and 10 mile options. The event uses 2.5 mile laps, provides aid at the start and finish, and donates 20% of entry fees to Forestry England.

An evening running event at Westonbirt Arboretum on 6 February 2027, with 5 km and 10 km routes that pass through collections of over 2,500 trees. The surface is solid underfoot and ticket sales are currently sold out.

A single-loop 53 mile trail race starting and finishing at Ditcham Park School in Petersfield. The route has about 6400 ft of ascent, six aid stations, full way marking and is worth 3 ITRA points.

Follow in the footsteps of ancient pilgrims on this 66 mile two day ultra adventure along the historic North Downs Way. Experience a supported winter trail challenge with overnight accommodation and full logistics included.

A winter running event through Westonbirt Arboretum's tree collections offering 5 km and 10 km wave entries on Sunday 7 February 2027. The organiser is Relish The Great Outdoors and tickets are currently sold out.

A 28.2 trail marathon along the River Adur in February, starting at Shoreham Sea Scout Hut, with muddy paths and fully stocked aid stations. Prior trail marathon experience, suitable clothing and a mobile phone are required.

Experience two distinct half marathons along the Hampshire coast over one weekend. Run the muddy trails of Langstone Harbour or the flat promenades of Southsea, with the option to complete both for a special bonus medal.

A measured 10 mile road race in Melksham with a route through Lacock, a finisher medal and prizes across age categories. The field is limited to 300 places and entries close on 1 January 2027 or earlier if full.

Dalwood 3 Hills on 14 February 2027 offers three off-road distances through hilly, muddy countryside near Dalwood Village Hall. Routes include river crossings, marshalled support and are held under a Trail Running Association licence.

Self-navigation coastal trail on the South West Coast Path around Portland on 14 Feb 2027. Marathon (two loops), Half and 10k follow looped routes; mandatory kit is required and entries are capped at 500.

A fully signed 50k trail ultra on the North Downs Way and Norbury Park with 2986 ft of ascent. Based at Denbies Wine Estate near Dorking, the route includes four checkpoints offering food and drinks.

Races in Bath that run through two restored railway tunnels, featuring distances from 500 m family Colourburst to an ultramarathon and a start and finish at Brickfields Park.

An annual 12 mile trail race around the Vale of Pewsey organised by Pewsey Vale Running Club, listed in Worlds Ultimate Running Races. Proceeds from the Terminator have helped the club donate over £101,000 to local charities.

Trail event in the Meon Valley on 21 February 2027 at Queen Elizabeth Country Park. Options include 16 miles, marathon or 50 km ultramarathon on single-lap muddy trails with two climbs to Butser Hill and stocked aid stations.

A 10 km multi terrain race from Windsor & Eton Brewery along Baths Island and Thames towpaths. The course is about half off road and the finish includes a pint cup and a free drink.

Coastal trail running from Eastbourne along the Seven Sisters with 10K, half, marathon and ultra options. Courses cross chalk downland and forest, are fully marked, timed, and form part of the Endurancelife season leaderboard.