Trail Running calendar near Henley-on-Thames 2026-2027

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.

Tackle the scenic 10 km Scorpion Run at Symonds Yat Rock in the Forest of Dean with winding trails and a final climb to the finish. Enjoy undulating gravel tracks, riverside views and a cafe at the start and finish for post run treats.

Experience an inclusive trail running festival at Dunstable Downs featuring distances from 1km to 10km. Enjoy a vibrant event village with live music, food, and family activities in a stunning landscape.

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.

Explore the Cotswolds at the Stroud Trails Event, offering four scenic trail distances from an 11 km quarter marathon to a challenging ultra. The route takes in hills, towpaths, and common land with full support and marked trails. Registrat..

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.

Experience a unique multi terrain 5k run through the fields and nature trails of West Lodge Farm Park. Watch for local animals as you navigate this rural course and earn a bespoke finisher medal.

Enjoy a flat and traffic free summer race series at Dinton Pastures Country Park. Choose from 5km or 10km distances with chip timing and a dedicated 2km kids run for a complete family evening.

Experience a 50 mile point to point journey along the scenic North Downs Way National Trail. This historic event takes runners from Farnham to Knockholt Pound with 5,600 feet of total elevation gain.

Tackle the scenic Berkshire Downs in this 26th edition trail running event. Choose between a 26.8-mile marathon or a 16-mile challenge on a mixed-terrain course. All finishers receive a unique pottery mug, and a free BBQ awaits runners.

Experience the world’s largest inflatable obstacle course at the iconic Brands Hatch circuit. Tackle a series of massive inflatable structures in this unique 5K event held in the heart of Kent.

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.