Trail Running calendar near Winchester 2026-2027

Choose a scenic 10k or shorter 5k through the Chiltern Hills around Frieth, combining woodland paths and country roads. Expect rolling climbs and panoramic views for a rewarding, hilly challenge for road and trail runners.

Trail race in an Area of Outstanding Natural Beauty around Biblins Youth Campsite, Ross-on-Wye covering approximately 6 miles or 10k on mixed trails and single track. Entry is limited to 200 runners and prizes include individual and team aw..

The Titsey Trail 10k is a community running event held on Sunday, 11th October 2026. Organized by runners for runners, it raises funds for a variety of local charities.

A community fundraising running event in Old Basing featuring chip timed 10K and 6K trail races plus a 2K family fun run. The event offers medals, prizes and refreshments with proceeds supporting Friends of Old Basing Schools.

MacTuffX Swindon at County Ground on 11 October 2026 offers solo, doubles and relay functional fitness races for ages 18 and over, combining ten Xercises with repeated 400 m or 800 m running segments.

A community off road running event in Marshfield on Sunday 11 October 2026 with children's and adult distances. Entries support Marshfield Primary School and the routes use temporary access across private land.

Trail running event at Blaise Castle, Bristol, with 1K, 5K and 10K options and free entry for under 16s. The event is organised by Black Trail Runners and includes course maps, photos and results.

Community organised *5k* near Aldershot on Sunday 11 October 2026 with a very flat route on the Polo Fields and Basingstoke Canal towpath, chip timing, a bespoke finisher medal, and a subsidised race t shirt option.

Trail running at Burnbake Forest near Corfe Castle on 17 October 2026 with routes of 6 km, 12 km and 24 km. The half marathon follows coastal ridge lines and includes one fuel outpost.

A 100 mile trail race from Goring & Streatley using Thames Path and Ridgeway routes in four 25 mile out and back spurs. The event has 16 aid stations, full medical support, a 28 hour cut off and mandatory kit and qualifier requirements.

An annual 25 km or 50 km challenge across Kent, Surrey and Sussex footpaths, navigated from written route directions with checkpoints, food included and a ten hour completion objective.

A guided 10 miles trail run around the Chilterns, following canals and reservoirs and passing Britain’s oldest post windmill. The event includes a run leader, trail technique instruction and a finisher’s medal.

A roughly 12K off-road race on 18 October 2026 that follows bridle paths along the Imber Range and passes close to the Westbury White Horse, with limited places, age and equipment restrictions, and finishing medals for all.

A multi terrain trail event in Stockland, East Devon on 18 October 2026 offering 10 km, 5 km and 3 km routes across fields, lanes and river crossings, with village hall HQ and on site refreshments.

Keynsham Dandy is an off-road race on 18 October 2026 organised by Town and Country Harriers; the roughly 12.5 mile course starts in Keynsham and includes the revived Compton Dando route with a stream, with Race HQ at The New Inn.

Woodland half marathon and 10k at Bedgebury National Pinetum in Kent on 18 October 2026, with traffic-free forest trails, downloadable GPX maps, medals, free photos and limited free parking.

An off‑road cross‑country race in Hardwick, Buckinghamshire, covering about 6 miles across varied terrain and water crossings. Entry is limited to 300 runners, with medals and category prizes including team awards.

The Blackdown Hill Challenge on 18 October 2026 is a trail running event from Fernhurst Recreation Ground to the Temple of the Winds, featuring a 866 ft climb and wide views. A shorter adult trail of about 4.5 km is also offered.

A 5k night trail at Dunkertons Park in Cheltenham where runners use head torches to light the course. Open to ages 16 and over, with prizes for top three men and women and on-site refreshments and safety rules.

Beachy Head Marathon Weekend runs multiple trail distances from a 10k to an ultra near Bede's Prep School in BN20 7XL on 24/10/2026. Runners comment on clear signage, friendly marshals, stocked aid stations and hilly coastal terrain.