Portsmouth
Trail Running Calendar near Portsmouth 2026-2027
Explore the top trail runs near Portsmouth for 2026-2027! We've gathered 96 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail routes of 21.3K, 16.5K and 12K from Goodwood Racecourse through the South Downs with varied terrain, views and on-course support.
Nighttime trail run around Winchester on signed routes including the South Downs Way, offered in 12 km and 22 km options with mandatory headtorches.
Free, community guided trail runs in south east England with a run leader, tail runner, social pace and limited places; membership is free and advance registration is required.
Trail run from Roundhill Campsite in the New Forest with wide gravel paths, roaming wildlife and three distances around 21.6K, 16.7K and 10K.
Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.
MoRunning at Southampton Common offers chip timed 1.5k, 5k, 10k and a half marathon with medals, finisher headbands and on-site race facilities. The course mixes paths, trails and grass and is dog friendly and buggy usable.
A 10 miles off road trail race in the New Forest on 22 November 2026, organised by Totton Running Club with limited entries and race day facilities.
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey with hills, group navigation, kit support, parking and scheduled sunset and night dates.
A guided 30 mile trail run from Haslemere on the Serpent Trail and Sussex Border Path, led by an experienced ultra runner at a social group pace.
A festive Santa Dash in Northchapel on Sunday 29 November with 5K, 2.5K and a toddler scramble, medals for finishers and funds raised for Northchapel Village School.
December 2026
A festive seaside run in Portsmouth on 6 December 2026 with the Arkansas Chuggabug, a flat course, themed medals, spot prizes and timed long-run options; entry capped at 100 places, fee £20.
A 10 mile cross country run in West Wight on 13/12/2026 with hilly coastal scenery, limited entries and an entry fee of £27.50.
A timed festive event on the Itchen Way in Winchester with flexible rock up start times, a measured out-and-back course, lap options up to ultramarathon distance, and a bespoke finisher medal.
A festive coastal running weekend in Portsmouth on 20 December 2026 with a marathon, half marathon and a new 12km of Christmas on flat multi-terrain routes.
A six mile multi terrain group social run at Bembridge Youth & Community Centre on 20 December 2026 with entry including a souvenir, soup and roll.
Traditional 3.5 mile run from the Devils Punch Bowl Hotel across Hindhead commons via Gibbet Hill with chip timing and all profits to Holy Cross Hospital.