Trail Running calendar near Winchester 2025-2026

Leith Hill Half Marathon is a challenging 13.1 miles trail race across Surrey with about 1,800 feet of ascent and a summit finish at Leith Hill Tower. Enjoy scenic singletrack, a reusable medal, local beer and a full cooked breakfast.

Wight Riot is a mixed terrain coastal run at Hordle Cliff West, with sweeping views of the Isle of Wight and a scenic stretch past Sturt Pond Nature Reserve. Choose distances from 5K to ultra marathon and earn a medal for completing a lap o..

Enjoy a scenic riverside run along the Thames Path with options from 10 km to a full marathon. Flat, runnable routes marshalled and supported with checkpoints, food and medical cover make this a great spring challenge in Barnes.

Take on the Steyning Stinger on Sunday 8 March 2026 with marathon, 30k or half marathon routes across the scenic South Downs. Enjoy a sustainable UK made finisher medal, free race photos, post event breakfast and a green and gold technical..

Larmer Tree 2026 invites runners to the picturesque Larmer Tree Gardens on the Rushmore Estate in Dorset, with courses run in laps from a 1 mile fun run up to the marathon and a full colour finishers medal. Held Sunday 8 March 2026, entries..

Join the women focused TrailX Women Run at Culden Faw Estate near Henley on Thames on 8 March 2026 for a scenic day on the trails. Multiple distances from a 3 km fun run to 13 km competitive options make it perfect for all abilities.

Take on the Hundred Hills 50 km, a scenic trail ultra through the rolling Chiltern countryside around Stonor Park on 14 March 2026. Two 25 km loops, big climbs and forest tracks make this a rewarding and rugged challenge.

Run along Dorset coast from Swanage to the ruins of Corfe Castle, passing Old Harry Rocks and Studland for stunning sea views. Choose 10.5, 16.5 or 21 km and enjoy chip timing, a finisher medal and a unique return on a private steam train.

Run the scenic Maverick Hampshire Trail at Matterley Basin near Winchester, tackling undulating South Downs trails past the River Itchen and through woodland on 24 km Half Marathon, 16 km and 5 km routes. Friendly vibe with on site parking.

Take on the Sevenoaks Circular Challenge on Mother's Day, 15 March 2026, a scenic LDWA event across the North Downs and Greensand Ridge with 15, 20 and 30 mile options. Expect indoor checkpoints, hot finish food and friendly marshals.

Take on Phoenix Running's Octopus Run on 15 March 2026 at Walton on Thames for a scenic towpath challenge along the River Thames, with distances from 5 km to ultra and flexible start times. Finish your effort and collect a bespoke finishers..

Join the Pendock Spring Chicken Run on 15 March 2026 for scenic Worcestershire routes with 10K, 5K and a 1K fun run for all ages. Enjoy medals, prizes and help raise funds for the local school.

Join Gratitude 25KM 2026 in Broxbourne for a rewarding 25 km run on 21 March 2026. Ticketed entry and a welcoming atmosphere make it ideal for runners looking for a spring challenge.

Experience the South Downs Way at Winter's End on 21 March 2026 with a point to point 50 mile ultramarathon from Arundel to Winchester or pick one of two marathon sections. Rewarding chalk ridge trails, ancient woodlands and well stocked ai..

Guided 13 mile trail run from St Martha's Hill through the Surrey Hills and parts of the North Downs Way, including Shere and Newlands Corner. Not a race, this social group run is paced at around 10 min per mile and may finish with an alcoh..

Run scenic Hampshire trails at Stansted House Trail Run on Saturday 21 March 2026, choosing 9.5 km, 15.5 km or 21 km routes through Stansted Park. Expect chip timing, marshals and a finisher medal; water stations are plastic free so bring a..

Bratton Hilly 11K on 21 March 2026 invites runners to tackle a scenic multi terrain course with challenging climbs and panoramic views around Bratton, Wiltshire. Places limited to 200 and all finishers receive a medal.

Run or walk the scenic North Downs Way in Surrey with Y2Y, choosing 26.2 mile or 14 mile routes that finish at YMCA East Surrey, Redhill. Waymarked routes, support stops, GPS files and finish showers, all raising funds for YMCA East Surrey.

Take on the Forest of Dean Spring Trails Half Marathon, a scenic way marked trail loop through ancient woodland starting and finishing at the Speech House Hotel. Organised by the local Rotary Club, it is chip timed and supports charity.

Explore flat, well kept trails around Windsor Castle with 10K and half marathon options plus a RunThrough Foundation place. Chip timed racing, free photos and post race food and an event village make it a great day out.