Trail Running calendar near Winchester 2026-2027

Join the Penshurst Village Cross Country Run on Sunday 3 January 2027 for challenging 5 mile and canicross races over scenic local trails and open ground. Enjoy a friendly village atmosphere and a great day out for runners and their dogs.

A 43 mile point to point ultra from Wendover to Little Venice, London, mixing country trails and Grand Union Canal towpath. The race includes GPS tracking, five checkpoints, baggage transfer, mandatory kit and an 11 hour cutoff.

The Doughnut Dash is a flexible-distance run along a flat Thames riverside trail. Participants can run from a single lap to ultra marathon distances while enjoying doughnuts. All finishers receive a custom, neon-colored medal.

A countryside trail run around Farley Mount in Hampshire with two route options, including a Half Marathon. The course is rolling with tree-lined sections and vistas, starts at Sparsholt College with ample parking, and offers finisher medal..

This trail run through Moors Valley Country Park offers a half marathon and a 10K on woodland gravel paths. It's a dog-friendly event with chip timing and an eco-medal. Be prepared for muddy sections and inclines on the scenic course.

The May Hill Massacre is a demanding 7-8 mile cross-country run in Gloucestershire, featuring steep climbs and muddy trails. A longer 14-15 mile Mayhem option is available for those seeking an extra challenge.

A 10 miles and 5 miles trail race at Pippingford Park Manor with hard packed trails, about 1568 ft of climbing and panoramic views. The event includes bespoke medals, cash prizes for podium finishers and free parking.

Race through the spectacular winter landscape of Westonbirt Arboretum after dark. Choose from 5km or 10km distances on a solid, road-like trail. Explore over 2,500 species of trees under the night sky.

The Hibernal Hills 50 mile is a season-opening ultra on a 53-mile loop from Queen Elizabeth Country Park. With 6400 ft of climb on 99% trail, it's a UTMB Index race requiring a marathon qualifier. Runners are supported by six aid stations a..

Run through the stunning Westonbirt Arboretum, home to over 2,500 tree species, on a solid surface perfect for a scenic race. Choose from 5 km or 10 km distances with multiple wave starts for this popular winter event.

The Portsmouth/Langstone Coastal Half Marathons offer two scenic coastal routes over Valentine's Weekend 2027. Run the trails of Langstone Harbour on Saturday and a flat loop from Southsea on Sunday. Complete both days for a special bonus m..

Event Overview The Wiltshire 10 is a 10-mile running event. It starts and finishes at the King George V Playing Field in Melksham. The route goes out towards the picturesque village of Lacock. Location & Facilities The event is based at..

Run 50k on the fully signed trails of the North Downs Way and through Norbury Park's ancient woodland. This trail ultra features four well-stocked checkpoints and is based from Denbies Wine Estate. Finishers are awarded a commemorative meda..

A running event on 6 March 2027 featuring a 45 mile loop around the City of Bristol, with 45 mile and 30 mile entry options, paired entries, upgrade and transfer choices, and transport available to the 30 mile start.

A women's trail running event at the Culden Faw Estate near Henley on Thames. It features three different trail distances: 13 km, 6.5 km, and a 3 km option.

The Serpent Trail event offers a scenic run through the South Downs National Park on 3rd July 2027. Choose from five distances, from 10km to 100km, on a trail passing heathlands and woodlands. The event includes transport to the start and w..