Trail Running calendar near Chesham 2026-2027

Experience a scenic trail run through the South Downs featuring 20k, 10k, and junior distances. This well organized event includes chip timing, finisher medals, and hilly routes with views over the Cowdray and West Dean Estates.

Join the Dilton Dash on 10 May 2026 at Dilton Marsh for scenic multi terrain 10K, 3K and 1/2K fun runs supporting village causes. Expect stiles and gates, medals for all finishers and prizes for winners.

Explore the beautiful Chiltern Hills on this guided 30km trail running adventure. Enjoy 500m of ascent through woodlands and ridges with professional run leaders and a finishers medal included.

An inclusive UK trail running series offering 1K, 5K, 10K and kids races with free entry for under 16s, held at Dunstable Downs in May and Blaise Castle Estate in October 2026, with activities, food and live music.

Hairy Legs is a cross-country charity event for all ages, held on a scenic, hilly woodland course. Distances are based on unmeasured loops, and there are solo, relay, and shorter youth options. Fancy dress is encouraged, with prizes and a f..

Experience a scenic single lap trail race through the bluebell woods of Hampton Estate and Puttenham Common. Enjoy chip timed racing with bespoke medals and onsite refreshments in a beautiful Surrey setting.

A multi-distance trail event in the Cotswolds on 10th May 2026, featuring quarter, half, marathon and Ultra 40 routes across trails, towpaths and commons with marked routes, checkpoints and on-course water.

Enjoy a scenic trail run or walk through the village of East Hendred on an undulating 5k course. Kids can also join the fun with a 1k obstacle run around the sportsground.

Experience a ten mile multi terrain lap through the scenic Cotswold countryside and Coln Valley. This undulating course features fields, footpaths, and a river crossing near the historic Chedworth Roman Villa.

Experience a cross country run through the Hertfordshire countryside with 5km and 10km distances. This community event in Little Gaddesden includes junior categories and mini races for children.

A multi-terrain 5 kilometre race at West Lodge Farm in Desborough on 13 May 2026, running through fields, woodlands and farm trails. Finishers receive a bespoke medal and a virtual completion option is available; entries close 12 May.

A four-race summer series at Dinton Pastures offering 5 km, 10 km and a 2 km kids event across May to August. Organised by Barnes Fitness with chip timing, marshals, medals and pre bookable parking.

Experience a 50 mile point to point journey along the scenic North Downs Way National Trail. This 81 km trail race features 5,600 feet of climb and crosses historic landmarks from Farnham to the outskirts of London.

Trail marathon and 16 mile races across the Berkshire Downs with routes on the ancient Ridgeway, timing chips, aid stations every 3 to 4 miles and a hand thrown mug for finishers. Runners must meet a 7 hour cut off.

An inflatable obstacle course 5K at Brands Hatch in Kent on Saturday 16 May 2026. Recent bookings show 205 in the past week and participants report good organisation and onsite support.

The Semington Slog on 16 May 2026 features a 10 km and 2 km run from St Georges School. Routes explore the village and Kennet and Avon Canal towpath. Enjoy community activities, refreshments, and prizes.

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

Experience the beauty of the Cotswold Hills starting from the historic Sudeley Castle. Choose from five trail distances ranging from a 7 km short course to a 51 km ultra marathon through picturesque English countryside.

A timed lapped event at Mowsbury Park on 16 May 2026 offering distances from 5 km to ultra with a seven hour time limit, flexible start window and both medal and no medal entry options; places capped at 75.

Experience an obstacle course race through historic site landmarks and riverside trails in Henley on Thames. Choose from distances ranging from 5km to 21km or bring the whole family for the dedicated kids event.