Trail Running calendar near Windsor 2025-2026

Run a scenic 47 mile route from Chipping Campden to Painswick along the Cotswold Way, with rolling hills and varied trails. Support stations, live tracking and a finishers medal help you tackle the 15 hour challenge.

BigSky Trails concludes the Classic Element Trail Series, sending runners from Hyde Common across open plains and winding New Forest trails with wide horizon views. Choose 18 mile or marathon and take a bespoke medal or opt for a tree.

Event overview The Bradenham Blast takes place on Sunday 20th September 2026 and offers three trail distances: 5km 10km Half Marathon (21.1km) Routes run through beech woodland and across the Bradenham Estate in the Chiltern Hills, which..

Run scenic countryside trails at the Clipston Trail Half Marathon and Country 5 Miler, starting from Clipston Recreation Ground. Enjoy rolling hills, a homemade cake at the finish and the feel good factor of supporting local playing fields.

Join the Chiltern 50 Ultra Challenge from Henley basecamp and run scenic looped trails through rolling hills and nature reserves. Pick 50, 25 or 10 km routes with aid stations, camping options and a finishers medal at a lively basecamp.

Join The Pumpkin Run in Colchester on Sunday 27 September 2026 for 10K, 5K or a fun 1K family dash through scenic fields and a festive pumpkin corn trail. Expect chip timing, an event village, exclusive medals and plenty of family friendly..

Experience Cranborne Chase from Salisbury Racecourse on scenic undulating trails. Choose marathon, half marathon or 10k along ancient droves and woodland tracks, with parking, showers and a medal for every finisher.

The South Downs 100 mile (Autumn Event) is a challenging single-loop trail race held in the scenic South Downs National Park, starting at Plumpton Racecourse in Lewes, East Sussex. Covering 100 miles with over 12,000 feet of elevation, the..

Take on 25 km of scenic trails through Epping at the London EcoTrail, an eco focused run that blends challenge with beautiful countryside views. Perfect for trail lovers seeking a green, memorable race day.

Take on the scenic 50 km challenge through Epping Forest in London on 3 October 2026. Enjoy sweeping trails, leafy views and a rewarding long distance test for experienced runners.

Run to the Sea Bournemouth is a scenic 50 km point to point ultra from Moors Valley to Hengistbury Head, blending forest trails and seafront paths. Expect a mostly flat course, feed stations, free photos and a bespoke finisher medal.

Run beneath starry skies on the South Downs at The Dark Downs, a dusk to night trail event from Plumpton Racecourse near Lewes. Choose a 50k or half marathon on rolling, runnable trails with reflective signage and friendly aid stations.

Wild Run Cotswolds invites trail lovers to Cornbury Park for scenic, undulating single loop routes from 10K to the marathon plus a six hour 360 challenge. Family friendly, fully marked and marshalled, entries limited to 600 runners.

Enjoy scenic undulating forest trails at Alice Holt with 5k, 10k, Half Marathon and junior distances run over 5k loops. The event is postponed until Spring 2026 and raises funds for GUTS to support bowel cancer detection and research.

Push your limits at Loop Til You Drop Backyard Ultra at Turvey House. Run a 6.7 km loop each hour, starting on the hour, and see who lasts longest; single, paired and 7 Hour Max entries welcome.

Explore the Kent Downs from Maidstone this October with 50 km, 25 km and 10 km loops for walkers and runners. Support, camping, food and a finisher's medal and t shirt make for a rewarding weekend.

Join a guided 30 mile trail run from St Martha's Hill through the Surrey Hills, with views of Box Hill and Denbies Wine Estate. Run as a friendly group with an experienced ultra runner and coach to guide you every step of the way.

Tackle rolling climbs and sweeping Chiltern views at the Frieth Hilly 10 km and 5 km Run, set on mixed woodland paths and country roads. Expect a scenic but challenging route between Frieth and neighbouring villages.

The Centurion Autumn 100 will take place in Goring on Saturday 17 October 2026. This trail is organized by Centurion Running. You can run 100 miles.

Stort30 is a 30 mile ultramarathon along the River Stort towpath, flat and scenic, out and back from Bishop's Stortford. Toilets, showers and aid stations plus a finishers medal make it a friendly test for experienced runners.