Trail Running calendar near Winchester 2025-2026

The Wendover Woods Marathon, Half Marathon & 10k is a scenic autumn trail running event held in Wendover Woods, Buckinghamshire. The race features multi-terrain, hilly courses with significant climbs, making it a challenging yet rewarding e..

The Dorset Hillfort Ultra is a scenic 38-mile running event set in the picturesque West Dorset, featuring a challenging course with approximately 1,300 meters of ascent. Participants will traverse from one ancient hillfort to another, enjoy..

Join the WIM Founder's Trophy at Bere Wood on Sun 2 Nov with courses for all levels. Expect runnable woods, marshy patches, waterproof maps and electronic punching for a fun day out. Entries close 31 Oct.

Navigate ancient woodland, parkland and meadows at Dagnam Park in the HAVOC Regional and SWELL orienteering event with waterproof maps and SI timing. Courses suit beginners to experienced orienteers and help and coaching are available.

Join WRNL 3 in Colden Common for a lively 60 minute orienteering score event where you pick controls in any order to rack up points. Lights and hi viz required; hired dibbers available and juniors must be accompanied.

Take part in a woodland night score at Westerham: 60 minute navigation to collect as many 10 point controls as you can from 20 locations. Limited entries, book online in advance; apres and prize giving at The Carpenters Arms.

The The Druid's Challenge will take place in Tring on Friday 7 November 2025. You can run 86 miles.

Enigma Fireworks is a running event taking place on November 7th and 8th, 2025, at Caldecotte Lake in Milton Keynes. The event features both a marathon and a half marathon on each day, with participants completing scenic laps around the lak..

Run a twilight 10 km off road trail through Dorset woods and historic parkland as dusk falls. Enjoy atmospheric scenery, a touch of local ghost lore and medals, trophies and refreshments at the finish; entries are limited.

Run the Dirt Half Challenge in Leighton Buzzard this November, a scenic trail half marathon along canal towpaths, woodland and the Greensand Ridge. Finish with a lap of Tiddenfoot Waterside Park for a memorable autumn outing.

Tackle a 50 km ultra linking five classic long distance trails or choose a half marathon through chalk downland and woodland near Graffham. Enjoy stunning views, stocked checkpoints, SportIdent timing and an eco wood finisher medal.

Big Night Out Winchester is a torchlit trail run on the South Downs from Winchester Athletics Track with 12 km and 22 km options. Run by headtorch along ridges and rivers and opt to have a tree planted instead of a finishers medal.

Take part in a 7 hour Time Challenge on scenic Thames towpaths in Egham with a two minute silence for Remembrance. Mixed path and light trail loops offer aid stations and vegan snacks while you lap to marathon or ultra distances.

MoRunning returns to Ashton Court Park in Bristol on 9 November 2025 with 1.5k, 5k and 10k trail friendly routes that mix paths, mud and a testing hill. Support Movember for men's health, grab a finisher medal, wear fancy dress and join the..

Join the Southampton MoRun on 9 November 2025 at Southampton Common to support Movember and men's health. Choose 1.5k, 5k, 10k or the half marathon and enjoy a medal, headband and post race treats.

Take on a scenic Half Marathon along the Grand Union Canal through country trails and woodland on November 9, 2025. Enjoy chip timing, a finisher medal and a lively event village with refreshments and event photography.

The SATURN Remembrance Day Run 2025 - South is a commemorative running event held at Wraysbury Skiff & Punting Club, Egham, along the scenic River Thames. Participants can run a flexible distance within a 6 hour and 32-minute timed challeng..

Explore Shaw Forest Park, West Swindon on Sunday 9 November 2025 for an orienteering event with courses for beginners to experienced navigators across mixed forest and open terrain. Online entry only, limited maps available so book early.

Join the Wessex Night League in North Salisbury for a one hour score orienteering through urban streets and a hilltop nature park. Fast paced and social, bring lights and hi vis, and pre entry is required.

KNC 6 at Rusthall Common is a Kent Night Cup score event combining forest, urban and rock features in a 60 minute night challenge. Limited to 40 places and online registration only, so book early for an atmospheric evening orienteering.