Trail Running calendar near Winchester 2025-2026
We have found 387 Trailruns within 80 miles of Winchester. See below where and when you can find the races.
Distance (km)
Articles
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Enjoy a guided 10km trail run around Hindhead's Devil's Punchbowl, with scenic hilltops and a pause for the views. Runs run at sunset or at night with headtorches, led by an experienced trail coach and Salomon ambassador.
Run scenic trails from Plumpton Racecourse on the edge of the South Downs National Park with sea views and rolling countryside. Choose 21.3 km, 15.5 km or 10.8 km and enjoy chip timing, water stations and a finisher medal.
Join a guided 30 mile trail run from Haslemere, Surrey along the Serpent Trail with stunning South Downs views. A friendly group run led by an experienced ultra runner and coach, ideal for first time ultras and seasoned trail runners.
December 2026
Join a guided trail run at Box Hill, Dorking covering 12.5 miles with about 1000 m of ascent through steep, technical woodland and open fields. This noncompetitive group run suits fit trail runners and finishes with an alcohol free beer.