Trail Running calendar near Upper Woolhampton 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.

Experience the beautiful Dorset countryside on these primary trail routes through Thomas Hardy country. Choose between a 5 mile or half marathon course starting and finishing at Dorchester Rugby Club.

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.

A 10k off road trail run at Symonds Yat with undulating paths, river views and a steep final kilometre climb. Start and finish are at Symonds Yat Rock Cafe where coffee and hot food are available.

Experience a vibrant trail running series at Dunstable Downs or Bristol. With distances from 1km to 10km, this inclusive event features live music and food for a complete carnival atmosphere.

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.

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.

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 81 km trail race features 5,600 feet of climb and crosses historic landmarks from Farnham to the outskirts of London.

Experience the spectacular World Heritage coastline of Dorset by walking, jogging, or running various distances from 10km to 100km. Enjoy a fully supported route with rest stops, inclusive catering, and beachside finishes.

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.

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.