Trail Running calendar near Chesham 2025-2026

Take part in Festive 5 on 11 Jan 2026, a 5 mile off road run along the River Avon through Fladbury and Lower Moor. Organised by Friends of Fladbury, this fundraiser offers free cake, spot prizes and supports local community projects.

Warm up your winter with the Winter Hot Chocolate Series, three friendly cross country races around Bramshill Plantation based at St Neot's School. Enjoy chip timing, themed medals and hot chocolate treats, plus a fun 1 mile kids race.

Explore the New Forest at Kings Garn Gutter on Sunday 11 January with courses for all levels from novice path courses to challenging long routes. Fast runnable forest, updated maps and onsite catering make it a perfect winter orienteering d..

Join a guided 10 km trail run at atmospheric Hankley Common, exploring open trails, the Lion's Mouth and famous filming locations. Runs are led by an experienced trail guide and include sunset and night runs with headtorches for extra adven..

Enjoy a scenic road race along Windmill Way from Bury St Edmunds through picturesque villages to Dalham with windmill and Dalham Hall views. Distances from 5k to ultra on rolling hills; bring your own bottle for the cupless event.

Maverick New Forest Gravel invites runners to explore scenic gravel trails and woodland mud on 6 km, 12 km or 22 km routes. Bring a reusable cup and you can run with your dog.

Take on the iconic Box Hill fell race on Sat 17 Jan 2026 from the Stepping Stones pub, a challenging 12 km route with 530 m of climb and sweeping Surrey views. Pre entry only and entries fill fast, so be ready when entries open.

Take on the Arundel and SDW Winter Trails 2026, a point to point off road run from Heyshott to Arundel by Arundel Castle. Choose marathon or 15 mile routes through rolling fields and riverside trails and cross a scenic suspension bridge.

Join Ryde Harriers for a three race cross country series at Smallbrook Stadium in Jan and Feb 2026, with a testing 10 km course and a 6.5 km youth option. Expect varied terrain, team trophies and friendly club racing with limited entries.

Run the Benfleet 15, a scenic 15 mile multi terrain challenge at Hadleigh Country Park including parts of the 2012 Olympic mountain bike course and Canvey sea wall. Bespoke medal, free photos and prizes. Bring your own cup.

Join The Dirt Run, a two round multi terrain series in Northamptonshire with trails, paths and a muddy hill to conquer. Choose 5 km to 15 km routes and collect a custom finisher medal amid scenic parkland.

Night street orienteering in Chelmsford as part of the Essex Winter Midweek Series. Use MapRun or printed waterproof maps to tackle Long or Short courses through roads, paths and parks under torchlight for series points.

Take on a three hour trail challenge from Holmbury St Mary and complete as many 5 km laps as you can across scenic Surrey Hills trails and the climb to Holmbury Hill. Entry includes a bowl of chilli or curry and a headtorch is required.

Tackle a wet and hilly trail at Bagshot on Saturday 24 January 2026, with splashy puddles and twisting climbs to test you. Choose a single lap 5 km or two lap 10 km for a muddy, adventurous winter race.

Join the Stonehenge Stomp on 25 January 2026 for a scenic walking event that welcomes runners and is not a race. Choose routes from family friendly 5 km up to 40 km and enjoy stunning views of Stonehenge in a popular, limited entry event.

Tackle scenic trails at the Ashdown Forest 10 mile or 5 mile race on 25 January 2026 from Pippingford Park. Enjoy testing climbs, wide views across The Downs, free parking, a bespoke medal and cash prizes.

Run Moors Valley Country Park on the Wildwood Trail Series half marathon or 10K through woodland trails with muddy sections, climbs and chances to spot deer and birds of prey. Chip timed race with great marshals and a wooden finisher medal.

Take to flat, scenic trails through Alexandra Gardens beside Windsor Castle with chip timing and friendly post race goodies. Choose 10K or half marathon, enjoy well marked routes, free photos and an event village for food and drinks.

Join the G3 Series on Saturday 31 January 2026 for scenic 15 km and 10 km runs near Hound House Road in Surrey. Friendly, well signed courses and easy parking make this a perfect winter tune up for runners of all paces.

Run scenic trails on the South Downs at Queen Elizabeth Country Park with 8, 15 or 22 km routes through woodland and rolling chalk tracks. Dog friendly, timed and offering water stations and finisher medals, it suits runners of every level.