Trail Running calendar near Winchester 2026-2027

Run the South Downs Way from Heyshott to Arundel in a scenic point to point trail event on 18 January 2026. Choose a marathon or 15 mile off road route that finishes by Arundel Castle with river views and rolling downs.

A muddy off road trail race of about 9.6 miles through fields, woodland, a stream and along a riverbank in Thornbury. Finishers receive a metal medal and a bespoke buff; entries were via Full on Sport and the event is sold out for 2026.

Join a friendly three race cross country series at Smallbrook Stadium, Ryde, in January and February 2026, with 10 km and 6.5 km options. Expect classic country terrain, a lively club atmosphere and team scoring for the 10 km.

Join the Red Robin Run at Southwater Park on Sunday 18 January 2026 for a timed, flat trail challenge on the Downs Link where you can choose 5k to ultra distances on the day. Enjoy a festive Red Robin finisher medal and limited places.

Orienteering at Pippingford Park on Sunday 18 January offers courses for all levels across scenic woodland. Online entry required, parking fee applies and contactless SIAC punching is available.

Micheldever Forest SCOA League is an orienteering event on Sunday 18 January with courses from 2.1 km to 9.4 km on a 1:10,000 map, parking on gravel forest tracks and EMIT eCards in use.

Explore Amesbury by torchlight in a lively 60 minute score orienteering event with 24 controls, based at the New Inn. Pre entry is required, so bring lights and hi viz clothing, and juniors under 16 must be accompanied.

Join Esher Street O, part of the Winter Street O Series by Mole Valley Orienteering Club, at The Wheatsheaf in Esher. Choose a 60 or 40 minute score course with MapRun and relax with food and after the race refreshments at the pub.

Join the STAR Backyard Holmbury St Mary three hour trail challenge on 23 January 2026 and see how many 5 km laps you can complete around Holmbury Hill. A headtorch is required and entry includes a warm bowl of chilli or curry.

Brutal @ Bagshot serves up a muddy, hilly Army training circuit with bogs, twisting climbs and knee to waist deep water holes. The 10 km is two gruelling laps.

Huffin Puffin Run on 24 Jan 2026 at Xcel SPORTS HUB, Walton on Thames. Flat 5.3 km riverside loop with distances from 5 km to ultra; lap as you like within the time limit and enjoy aid stations and digital results.

Pick your distance on the day at Running Tribe Races in Chalfont St Peter and tackle looped trails through woods and footpaths. Distances from 7 km up to marathon and ultra are offered, with an aid station serving food and drinks.

The Stonehenge Stomp is a not timed walking event around Stonehenge with marked routes of 5 km, 10 km, 20 km, 30 km and 40 km and marshalled checkpoints. Fifty percent of proceeds support Salisbury Hospice Charity and entries are online onl..

Take on the Ashdown Forest 10 and 5 Mile on 25 January 2026 at Pippingford Park, a scenic trail run through rolling forest terrain with rewarding climbs and wide open views. Free parking, medals for all and cash prizes for podium finishers..

Choose a half marathon or 10K through Moors Valley woodlands with muddy trails, steep climbs and chances to spot deer and birds of prey. Finishers get a wooden medal and the course is fully supported and timed.

Take to flat, scenic trails through Alexandra Gardens beside Windsor Castle with chip timing and friendly post race goodies. Choose 10K or half marathon, enjoy well marked routes, free photos and an event village for food and drinks.

Tackle muddy trails and steep climbs at the May Hill Massacre, a scenic cross country run around May Hill in Gloucestershire. Choose a 7 to 8 mile route or the longer 14 to 15 mile Mayhem loop, with a canicross option and limited entries.

G3 no.2 brings a friendly winter race to Hound House Road, Surrey on Saturday 31 January 2026. Pick a 10 km or 15 km route and enjoy clear signage, field parking and a welcoming series atmosphere.

Starburster is a twilight 5 or 10 mile run through Hurn Forest on 31 January, with out and back laps on firm forest trails beneath sunset skies. Head torches are required and 20% of entry fees support Forestry England for trail care.

Oxford Town v Gown is an inter-club orienteering event in Oxford organised by OUOC and TVOC, featuring a roughly 6 km course with artificial barriers and team entries as Town, Gown or N A.