Trail Running calendar near Chatham 2025-2026

Take on the Chiltern 50 Ultra Challenge from Henley Showground and enjoy looped trails through the rolling Chiltern countryside, with walk, jog or run options to suit every pace. Basecamp adds camping, a Saturday meal and shuttle service.

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..

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 on 3 October 2026 is a point to point 50 km ultra from Moors Valley to Hengistbury Head, pairing flat scenic forest trails with seafront running. Course is fully signed with feed stations, a finish medal and event..

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.

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.

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.

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.

Endurancelife comes to Dunwich on 11 October 2025 with scenic flat courses through forest, moorland, grass and beach. Distances from 10K to a 32.7 mile ultra, fully marked, timed with medals and instant splits. Waitlist open.

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.

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.

Join Beachy Head Marathon weekend on 24 to 25 October 2026 for scenic off road runs across the South Downs with seafront starts at Eastbourne. Options include marathon, 52.6 km ultramarathon, half and 10K.

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.

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.

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.