Trail Running calendar near Winchester 2025-2026

Enjoy night and day races across Bath Skyline's stone paths, woodland trails and open meadows, with 5km, 10km and a kids 500m plus a dedicated daytime canicross wave. Glow stick marked night courses make for a magical running experience.

Experience torchlit trails and ancient ruins at the Maverick Dark Castle around Corfe Castle on 15 November 2025. Choose 5 km 10 km or 16 km routes for a thrilling off road night run hosted by Maverick Race.

Explore runnable forest at Shoreham Woods with courses for all abilities and a one hour score challenge. Online entry only; trails are shared with walkers, riders and bikers and have some steep slippery slopes.

The Rugged Radnage 10K Run, held in the Chiltern Hills near Radnage village, offers a challenging mixed-terrain course featuring roads, trails, footpaths, woods, and fields with notable ascents and descents. The event includes both 5K and 1..

Join the Smurf Run, a friendly 7 hour challenge along the Thames at Wraysbury. Finish 3 km to earn a Smurf themed medal and keep going to collect distance pins for half marathon, marathon and ultra achievements.

Join the inaugural FOBS 5K Trail Run and Colour Run in Box on 16 November 2025 and support Box Primary School. Choose a family friendly 800 m colour run or a chip timed 5K through scenic Bybrook valley, with treats and certificates for all.

Join the 5th Sundon Saunter for scenic undulating countryside with hilltop views, woods and field paths. Choose 13, 18 or 27 mile routes for walkers and runners starting from Barton le Clay village hall.

Roly's Run is a scenic Meon Valley trail loop from Swanmore via the South Downs Way, offering 15.5 mile, 21.5 mile and a tough 40 mile option. The event is full and new entries are placed on a waiting list.

Enjoy a small 8 mile trail race through the stunning Avebury World Heritage Site in Wiltshire, weaving past ancient stone circles and rolling countryside. Organised by Marlborough Running Club, this popular November event often sells out.

Enjoy a scenic but tough trail marathon or half marathon in Broadway, Worcestershire on 16 November 2025. Routes climb to Broadway Tower, pass Sudeley Castle and traverse muddy Cotswold tracks, and entries are full with a waiting list open.

Join Carshalton Street O for an evening of score orienteering in the Mole Valley Winter series, starting outside The Hope pub with food and post race refreshments. Pick 60 or 40 minute score courses and use MapRun to time your run.

Join a guided 10km trail run around the Devil's Punchbowl in Hindhead, enjoying rolling hills and a scenic pause with great views. This friendly group paced run is led by an experienced guide and runs at sunset or by headtorch in winter.

Run as many 5 km laps as you can in three hours around Peaslake Village Hall. A friendly night event with head torches, refreshments, prizes for top men and women plus shoe demos.

Dark Valley, Night Trails is a night-time trail run at Moors Valley Country Park, Ashley Heath, near Ringwood, Dorset. The 10km loop winds through wide, tree-lined forest tracks on the Hampshire/Dorset border, with 1, 2, or 3 laps for 10km,..

Enjoy a scenic, flat coastal run at the Bournemouth Coastal TEN, choose 10 mile or 10 km along Hengistbury Head and Boscombe Pier. Chip timing, a finisher medal and post race refreshments make it a perfect seaside challenge for all abilitie..

Explore Burghfield woods with Berkshire Orienteers on Saturday 22 November 2025. Five courses from a family friendly yellow to a challenging blue welcome beginners and seasoned navigators, with electronic timing and a scenic forest setting.

Explore 30 miles of the Serpent Trail from Haslemere in a hilly, scenic group run through woodland, heath and views across the South Downs. Led by an experienced guide, this non race suits runners ready for long trail miles.

Take on the New Forest Stinger, a scenic 10 mile trail race at Ocknell Campsite near Lyndhurst on 23 November 2025. Expect forest paths, supportive aid stations and a medal at the finish for a lively off road challenge.

The RunUk Kingston 10k is a scenic running event starting and finishing at the Kingston Hawker Centre in Surrey. The course takes runners through the streets of Kingston and along the picturesque river towpath, offering a vibrant atmosphere..

Run the trails from the highest point in the Chilterns at ATW Wendover Woods. Choose 5K, 10K, half marathon or 5K Canicross, soak up stunning countryside views and celebrate with a custom medal and finish line goodies.