Trail Running calendar near Winchester 2026-2027

Explore the scenic South Downs on this 10k trail run from Peacehaven. The undulating route takes in bridleways, the South Downs Way, and the historic Greenwich Meridian Trail. Participants receive a bespoke medal, photos, and refreshments.

A half marathon at Box Hill Fort on 28 June 2026 with more than 3,000 feet of ascent over mostly rough tracks. The route offers views of the North Downs, the Mole Gap, Denbies Vineyard and Dorking.

A guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey. Evening sessions include sunset runs or night runs by head torch and focus on group pacing, hilly trails, and scenic views.

Run the full 82 mile Essex Way from Epping tube to Harwich lighthouse over challenging trails and country lanes. Enjoy supported checkpoints, GPS tracking and a 24 hour finish window for an epic route across Essex.

Event Overview The Serpent Trail is a trail running event offering five distances: 100km, 75km, 50km, 20km, and 10km. It takes place on a long-distance trail through countryside in the South East of England, within the South Downs National..

Choose your own challenge at the Summer Sun Run, a flexible lap event set in the scenic Denbies Wine Estate. Complete as many 5.3 km laps as you like within 7 hours, with a large medal for all finishers. Enjoy a flexible start window and a..

A 21.1 km off road half marathon along The Ridgeway between Coombe Hill and Whiteleaf Hill, featuring 526 m of ascent, two on route aid station visits and full course marking near Wendover on 5 July 2026.

Two off road races around Bewl Water on 5 July 2026: a 15 mile route that includes the nature reserve and a 5 mile trail. The event is organised by Wadhurst Runners, supports the KSSAA, and features medals, t shirts, cake and beer.

A women only trail event at Denbies Wine Estate in Surrey on 5 July 2026 offering 50K, 25K, 10K and a kids race. No cut offs and options for in person or virtual participation, with profits supporting the SheRACES mission.

Trail races of 5 or 10 miles through forest tracks and lakeside paths at Moors Valley Country Park on 5 July 2026. The event includes chip timing, feed stations, medical support, and on-site parking.

A guided 10 km trail run through the scenic Thursley National Nature Reserve. Experience the famous boardwalk on this flat route, offered as both sunset and night runs. It's a group run with a steady pace, and head torches are provided for..

A 6-hour timed run along the flat Jubilee River in Slough on July 9, 2026. Participants complete laps of 5.24 miles, choosing their own distance. Every finisher gets a medal.

A flexible 7-hour timed run along the River Thames. Choose your own distance from 3km to an ultra, with a scenic, signed course. All finishers get a medal, snacks, and distance pins for longer achievements.

A multi distance trail event on the Ridgeway on 11 to 12 July 2026, finishing at the Avebury Standing Stones. It offers 50 km and 100 km options with signposted runnable trails, multiple pitstops and basecamp support including hot food and..

Explore the scenic Chiltern Hills on this trail run from Princes Risborough. Choose from five distances, from 8 km to a 50 km ultra, on a course featuring ancient woodlands and chalky paths. The event includes aid stations, a cup-free polic..

This unique 50 km coastal trail run in Dorset features a fun challenge: try to finish before the runner designated as "the Ferry." The scenic out-and-back course passes landmarks like Old Harry Rocks and Corfe Castle. All participants recei..

Run the Cider 5K.ish on Friday 17 July 2026 at Myncen Farm near Blandford Forum, a scenic one lap trail over fields, grass and dusty tracks. Part of a weekend of running and optional camping, this friendly race offers finisher goodies.

Take on the 12 hour Cider Challenge solo across undulating farm trails in Dorset this July 18, with fields, wildflowers and dusty tracks underfoot. Camp onsite for a full weekend vibe and earn a medal and goodies for every finisher.

BigHeat CampFIRE is a two day trail running festival at Mill Farm offering a 50 km ultramarathon, marathon, 16 mile, 12 km and a 2 km fun run alongside camping, yoga, live music and on course aid stations.

Race The Light is an evening trail run through the scenic Wendover Woods. Choose from 10K, 5K, or a 1.5K accessible route, with all proceeds supporting the Chilterns Neuro Centre. The fully marked course is open to runners, walkers, and whe..