Trail Running calendar near Winchester 2026-2027

We have found 411 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

Tackle iconic Box Hill on a trail running challenge in Surrey. Choose from 50k, 31k, or 21k distances on a clearly marked course with marshal support. Finish in the event village to collect your medal and post race goodies.

UTMB Index

Event Overview The Forest of Dean Ultra Marathon, also known as the FOD Ultra, is a 55 km trail running event. The route is a circular loop that passes through highlights of the Forest of Dean in England. The course is described as varied,..

Choose a scenic 10k or shorter 5k through the Chiltern Hills around Frieth, combining woodland paths and country roads. Expect rolling climbs and panoramic views for a rewarding, hilly challenge for road and trail runners.

Run a beautiful single lap through the autumn woodlands of Limpsfield Common. The 10k trail course features gentle slopes and a mostly downhill finish. Participants receive a medal, a finisher's T-shirt, and enjoy a supportive community atm..

The FOOBS Trail and Fun Runs return in October. Choose from a chip timed 10K, 6K, or a family friendly 2K fun run through the countryside near Old Basing. The event supports local schools through community fundraising.

Take on an ultra-distance trail run along the dramatic Jurassic Coast. Choose between a 102 km or 54 km route exploring the Isle of Purbeck, with fully marked courses and support outposts. The event is based at Burnbake Forest Lodges in Cor..

UTMB Index

Event Overview The Autumn 100 is a 100-mile continuous trail race. It takes place in the villages of Goring & Streatley on the River Thames. The event is scheduled for 17 October 2026. Course Details The course is shaped like a cross an..

UTMB Index

The Gatliff Marathon is an annual countryside challenge with 25 km and 50 km options. Walk, jog, or run on footpaths through Kent, Surrey, and Sussex, aiming to finish within 10 hours. Food, drink, and a finish line certificate are all incl..

Blaze the Biblins on 18 October 2026 is a scenic 10k trail race through ancient woods and riverbanks near Ross on Wye. Expect technical single track, climbs including the notorious Demon hill, and a lively village finish.

Roughly 12K trail run on bridle paths and the Imber Range near the Westbury White Horse on 18 October 2026. Limited to 200 places so book early for a bespoke finisher medal and category prizes.

A trail event near Honiton on 18 October 2026 offering 10 km, 5 km and 3 km courses across muddy, hilly farmland with village hall race HQ, on site refreshments and route maps.

Keynsham Dandy is an off-road race on Sunday 18 October 2026 around Keynsham. The roughly 12.5 mile course starts at The New Inn and includes the revived Compton Dando route with a stream feature.

Woodland half marathon and 10k at Bedgebury National Pinetum & Forest on 18 October 2026, with downloadable route maps, a bespoke medal, free photos and limited free parking.

A trail race weekend at Bede's Prep School near Beachy Head offering Ultra, Marathon, Half Marathon and 10k distances. Runners note scenic views, steep hills, clear signage and strong marshal support.

A 47-mile point-to-point ultra along the Thames Path from Iffley to Henley-on-Thames. The course mixes riverside trails with road sections and is a UTMB index race. Support includes five aid stations, GPS tracking, and a baggage transfer.

UTMB Index

A 5 mile timed, self-navigated night trail on 30 October 2026, run mostly through forest and downland. Fancy dress is encouraged with trophies and a post-run dessert for winners, and a tail runner will sweep the course.

A single-loop 50K trail ultramarathon in the Chilterns on 31 October 2026, starting and finishing in Berkhamsted with marked navigation, three aid stations and a 9 hour time limit.

UTMB Index

Run a night trail through Alice Holt Forest on a 5 km loop system. Choose your distance from 5 km, 10 km, or 15 km on wide gravel tracks lit by head torches. After the run, warm up by a fire pit with some food.

November 2026

A trail ultramarathon of about 36 miles around Maiden Newton, Dorset, with roughly 1,300 m of ascent, mostly off road and served by six aid stations. Navigation files and mandatory basic self-sufficiency kit are required.

Trail races in Wendover Woods, Buckinghamshire offer marathon, half marathon, 10k and a junior 1k on hilly forest trails with mixed terrain, onsite facilities and event medals and photos; there is a six hour cutoff.