Trail Running calendar near Winchester 2025-2026

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..

Run to the Sea Bournemouth is a scenic 50 km point to point ultramarathon that threads forest trails and coastal paths to a seafront finish at Hengistbury Head. Enjoy a fully signed route, regular feed stations and a bespoke medal on 3 Oct..

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.

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.

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.

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 The Maverick Jurassic Coast X-Trail will take place in Corfe Castle on Saturday 17 October 2026. This trail is organized by Maverick Race. You can run between 13 and 56 kilometers.

Take on Autumn 100, a scenic 100 mile trail challenge around Goring and Streatley along the Ridgeway and Thames Path. Four 25 mile out and back spurs, 28 hour cutoff and a field limited to 250 starters make for a classic long distance test.

Blaze the Biblins is a lively 6 miles trail race through ancient woodland, riverside paths and historic ironworks, featuring climbs and technical single track. Enjoy prizes, a memento and post race tea and cake; entries are limited.

The Beachy Head Marathon will take place in Eastbourne from Saturday 24 October 2026 to Sunday 25 October 2026. You can run between 10 and 53 kilometers.

Run across the sands of West Wittering at the Witterings Beach Run this November, with 5 km, 10 km and 15 km options and canicross entries. Enjoy coastal views, chip timing and a finisher medal on a plastic free, dog friendly course.

Run the rolling South Downs from Goodwood Racecourse this November, with 12km, 19km or 21km trail options. Tackle chalk tracks, forest trails and big views, enjoy on course support, chip timing and a finisher medal, and dogs are welcome.

Join the Windsor Trail Run on Sunday 8 November 2026 in Alexandra Gardens, Windsor for 10K and half marathon off road routes through royal Berkshire. Chip timed races, friendly marshals, an event village and tasty post race goodies await.

Explore ancient woodland and open heath in the New Forest with 10 km, 17 km or 22 km trail options. Enjoy waymarked gravel paths, on course support and a finisher medal, and note water stations are plastic free so bring a reusable cup.

Take in coastal views on the Bournemouth Coastal TEN at Hengistbury Head, with 10mi and 10km traffic free routes along the seafront and Boscombe Pier. Enjoy chip timing, a finisher medal and post race refreshments.

Join a guided 10km trail run around the scenic Devil's Punchbowl in Hindhead, with climbs and a summit pause to soak up the view. Enjoy sunset sessions or headtorch night runs led by an experienced trail coach in a friendly group.

Join a guided 30 mile group trail run from Haslemere led by an experienced ultra coach, through ancient woods, heath and valleys with views from the Temple of the Winds to the South Downs. Suitable for trained runners; tickets sold out.

Test your trail legs on Box Hill Vertical KM, a guided 12.5 mile run near Dorking that crams 1000 metres of ascent into a scenic but technical route. Run as a group through woodland, heathland and open fields with kit support and shoe trial..