Trail Running calendar near Winchester 2026-2027

Join the Winchester Trail Run at Sparsholt College for scenic 12 km and 21 km off road routes through rolling Farley Mount countryside. Enjoy tree lined tracks, a short climb to Farley Mount on the 21 km and a finisher medal.

Join the Festive 5 on Sunday 11 Jan 2026 in Worcestershire for a scenic five mile off road run along the River Avon through Fladbury and Lower Moor. Community event with proceeds supporting local projects and the Neuroendocrine Cancer Chari..

Join Ruby Red Running for guided social recce runs on sections of the East Devon Round in early 2026. Qualified guides tailor groups by ability, routes link via Honiton and Axminster with train options, and a small donation applies to those..

Kings Garn Gutter orienteering in the New Forest on Sunday 11 January offers runnable forest, streams and updated 1:10,000 maps. Courses range from short novice path events to long technical routes so all abilities can join.

Take on navigation at West Woods near Marlborough in a regional orienteering event in mature woodland. Courses suit beginners to experienced orienteers, parking is limited so car sharing is encouraged and entry is online only.

Join a guided 10km trail run at Hankley Common with a friendly group rather than a race. Explore the Atlantic Wall replica and famous film locations while enjoying scenic trails at a steady, social pace.

Take on a one hour night score at Buchan Country Park with 20 controls to find in any order. Bring a torch, whistle and warm layers for an adventurous evening of navigation and friendly competition.

Enjoy gravel trails through ancient woodland in the New Forest at Maverick New Forest Gravel on 17 January 2026. Choose from 22 km, 12 km or 6 km routes with scenic forests, wildlife and a friendly festival vibe.

Run under starlit skies in the Dark Skies Series, a winter night trail series across Somerset offering three events with 5km or 10km routes. Enter single races or the full series and order a bespoke wooden finisher medal.

Tackle a classic Box Hill fell race with a fully marked 12.8 km circular off road route and about 540 m of ascent, starting and finishing on Burford Spur. Enjoy challenging terrain, great views and competitive club racing under FRA rules.

Join the Tiaras & Tutus Orange Run on 17 January for distances from 5 km to ultra along a flat riverside towpath. Enjoy a flexible one hour start window, seven hour time limit and bespoke finisher medals in a fun, limited field event.

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.

Enjoy a lively winter trail of about 9.6 miles along riverside paths, woods and fields with stream crossings and likely mud. All finishers get a metal medal and bespoke buff, and the race forms part of the Thornbury Running Club series.

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.

Run orienteering in Micheldever Forest on Sunday 18 January with an updated ISOM map and courses for all abilities. EMIT eCards, parking on forest tracks, toilets and nearby pubs make it a convenient winter forest adventure.

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.