Trail Running calendar near Windsor 2026-2027

Experience a weekend of trail running at the picturesque Deene Park Estate featuring multiple challenges including a 10k evening run and a hilly half marathon. Tackle individual races or take on the full 56.1k quest.

Experience a variety of trail running and walking events at Mapledurham near Reading. Choose between ultra distances, half marathons, or a six mile walk featuring a river boat crossing with on site camping available.

Experience a 40 mile linear journey along the ancient Ridgeway track through the scenic downlands of Wiltshire and Berkshire. This event for walkers and runners offers a supported route from Avebury to Streatley.

This event on the Thames features 10K, half, and marathon distances on scenic riverside paths. Starting from the Wraysbury Skiff Club, the courses use fully marked out-and-back loops. The area near Runnymede offers beautiful countryside and..

Experience the twilight beauty of Ardingly Reservoir during this evening run in West Sussex. Choose between a 5K or 10K distance on an undulating trail course featuring scenic water views and a finisher medal.

Celebrate the 30th anniversary of this award winning marathon through the scenic rolling hills and hidden back roads of North Essex. This well supported event features a community focused atmosphere and low traffic rural course.

Experience a unique multi terrain race through the historic Northamptonshire countryside starting in Naseby. Choose from five distances ranging from a 10K road race to a 35 mile ultra marathon with rotating course directions each year.

Experience a scenic road race through the undulating Suffolk countryside with marathon and half marathon options. This measured course features quiet roads and local aid stations for a rewarding running experience.

Experience a scenic off-road trail run at Milton Creek Country Park while supporting neonatal care. This event features 10K and 5K distances plus a Junior Run, complete with bespoke medals and a friendly atmosphere.

Experience a carbon neutral trail run through the beautiful vines of the Rathfinny Wine Estate. Choose between a 10.7 km or 21.4 km hilly loop with views of the South Downs National Park.

A self-guided 13-mile run along Letchworth's scenic Greenway trail. This is a run, not a race, due to road crossings. Finishers get a wooden medal and refreshments, with profits supporting a local youth mental health charity.

Experience a scenic trail run through the South Downs featuring hilly terrain and beautiful views. Young runners can choose between 3km and 5km marshalled courses ending with an exciting descent to the finish line.

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.

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.

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..

Join a trail running and walking event in the village of East Hendred. Choose between an undulating 5k circular route or a 1k kids obstacle run at the local 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 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.