Trail Running calendar near Chesham 2025-2026

We have found 381 Trailruns within 80 miles of Chesham. See below where and when you can find the races.

Run 60 km along the ancient Ridgeway from Ivinghoe Beacon to near Wallingford across chalk ridgelines and rolling downs. With 1000 m ascent, a 10 hour limit and UTMB World Series status, this scenic ultramarathon tests endurance and pace.

Run through Southampton Common on 31 May 2026 amid woodland, lakes and wetlands. Choose half, 10K, 5K or junior distances and enjoy a lively event village with food, freebies and a sustainable focus.

June 2026

Join a guided 13 mile trail run around Guildford's Surrey Hills, visiting St Martha's Hill, Shere and the North Downs Way. Enjoy a friendly group pace, kit support and optional post run refreshments.

Join the Griffin Challenge at Braybrooke Taproom on 3 June 2026, a six hour looped event on the Griffin Trail where runners, walkers and hikers do as many laps as they like. Celebrate after with coffee, pastries and a cold beer.

Event overview The event takes place on Friday, 05 June 2026 as a 7 hour timed challenge. Participants may run any distance they choose within the time limit. The minimum distance to be an official finisher is 3 km. The normal lap length is..

The Sundowner Marathon is a unique running event held in Purleigh, Chelmsford, England, featuring a scenic course that passes along canals, over waterfalls, through vineyards, woodlands, and coastal saltmarshes. This marathon offers a disti..

Run through two lit railway tunnels beneath Bath on routes from short fun runs to ultra distances. Starts and finishes at family friendly Brickfields Park and each entry supports Sustrans, making it a memorable community day out.

Pick 5k, 10k, half, marathon or ultra on a scenic, undulating multi terrain course around Bury St Edmunds. Limited to 300 runners, with on course aid, included parking and a bespoke finisher medal for a memorable off road challenge.

A lively fell race on Coombe Hill near Wendover on 7 June 2026, tackling 7 km with 220 m of climb and rewarding hilltop views. Entry on the day, modest fees and a pint included make this a friendly, competitive outing for juniors and teams.

Join Chase The Sun at Clapham Common on 10 June 2026 for an evening 5K or 10K on a flat, scenic park course past the bandstand. Expect chip timing, free photos and a unique themed medal to celebrate your finish.

Nene Valley Trail Run on 13 June 2026 invites runners to explore rolling Northamptonshire countryside from Castle Farm Campsite. Choose 10 or 20 miles of fully marked trails through bluebell woods, riverside paths and quiet villages.

Tackle 100 miles of rolling chalk ridgeline in the iconic South Downs Way 100 on 13 June 2026, starting at Matterley Bowl. Fully marked route, stunning coastal and countryside views, and full aid support make this a classic ultra challenge.

Tackle the scenic South Downs Way 50 km on 13 June 2026, a fully supported trail across the chalk ridge. Part of the World Trail Majors Short Series, it features four aid stations and a 9 hour cut off.

Take on the Cotswold Way Ultra Challenge from 13 to 14 June 2026, based in Cirencester, with routes from 10 km up to a 100 km loop through classic Cotswold trails. Fully supported with campsites, catering and a finisher medal and tee.

Scenic off road trail running around Bewl Water in Kent, with forest paths, open countryside and lake views. Choose 10km, Half Marathon, Marathon or 50km Ultra, starting and finishing at the Visitor Centre with chip timing and checkpoints.

Run 14 miles across the dramatic South Downs on 14 June 2026, featuring a stiff climb, chalk descents and muddy slippery sections. Trail shoes recommended; enjoy water on course, post run cake and a commemorative truckers cap.

Tackle scenic but hilly forest trails at the Wendover Woods Half Marathon and 10k on 14 June 2026, with a friendly junior run and on the day entries if available. Spectators can enjoy a cafe, forest walks and family activities.

Run across the iconic chalklands of Watership Down at the Hampshire Hoppit. Choose marathon, half marathon or 10K single loop trail courses and toast your finish with a real ale.

Take in Hertfordshire countryside from 3 Brewers Brewery on scenic, undulating off road trails with 10km or 5km options. Finishers get a medal and a pint, with live jazz, food and fundraising for local charity Earthworks.

Run the Robertsbridge Midsummer 10k or 5k on 19 June 2026 at Robertsbridge Rec Ground, a friendly community race over a scenic undulating multi terrain course. Finishers get bespoke medals and can refuel with a BBQ and post race bar.