Trail Running calendar near Winchester 2025-2026

We have found 318 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

Take on the Serpent Trail in the South Downs on 4 July 2026, with routes from 10 km to 100 km across heathland, ancient woods and chalk hills. Camping, coach transfers, food and a licensed bar make it a perfect weekend for runners and walke..

UTMB Index

On 5 July 2026 the Chiltern Ridge Half Marathon offers a scenic off road challenge along The Ridgeway near Wendover, with rolling climbs and woodland views. Entries are limited to 350 runners so book early for this memorable trail experienc..

UTMB Index

Explore Thursley Common on a guided 10km trail run, a notably flat route with a scenic boardwalk and plenty of birdlife and dragonflies. Enjoy a friendly group atmosphere with kit to try and optional post run refreshment.

Run the Ridgeway to the Avebury Standing Stones in Race to the Stones, with 50 km and 100 km options including a two day format. Scenic trails, marked course, pitstops and full support make this a bucket list ultramarathon.

The The Maverick Chilterns Trail will take place in Wendover on Saturday 11 July 2026. You can run between 10 and 51 kilometers.

BigHeat CAMP FIRE is a festival style trail weekend at Mill Farm in the Surrey Hills, pairing single lap scenic trails with a fiery communal vibe. Choose from 2 km to a 50 km ultra, then unwind with camping, live music and yoga.

The Cider 5K.ish is a one-lap, 5-kilometre trail run/walk set on Myncen Farm in Minchington, near Blandford Forum, Dorset. The undulating course takes you across fields, grass, wildflowers, crops and dusty tracks on private farmland with pe..

The Cider Challenge Solo is a 12-hour trail-running event held on a privately owned farm in Dorset (Myncen Farm, Minchington, Blandford Forum, DT11 8DH). Designed for solo runners, with the option to enter as part of a team, participants ha..

Run through scenic Wendover Woods with 5K and challenging 10K trail options plus a 1.5K accessible loop. Limited to 500 runners, with chip timing and a finisher medal for all.

Event overview The Apple Plod 10K.ish is a trail running event on Sunday, 19 July 2026, organised by Running Events Devon. The race distance is 10K and is described as undulating trail on a two-lap course. Participants may run or walk; ther..

Run the ATW St Albans Summer 10K on 19 July 2026 at Highfield Park for a chip timed 10 km along the Alban Way, with a free family fun run. Festival vibes with live music, kids activities, food stalls and a custom medal while supporting Alzh..

Experience the Wye Valley Tunnel Run, racing through the atmospheric Tidenham Tunnel and scenic riverside and old railway paths. Distances suit everyone from a Colourbust family fun run to a full marathon, with trail charm and big event ene..

Join a friendly 7 hour timed run along the Thames at Wraysbury, with flat paved loops suitable for road shoes. Pick distances from a 3 km loop up to marathon and ultra, and enjoy a medal plus goody bag and riverside views.

Enjoy a scenic, flat trail run around Maidenhead Commons and Summerleaze Lake on Sunday 26 July 2026. Choose 5K, 10K or half marathon and earn a themed medal with free race photos, chip timed results and a lively event village.

August 2026

Join the North Downs 50 Ultra Challenge on Sat 1 Aug 2026 for scenic runs from Guildford across Surrey hills and the North Downs Way. Choose 10 km, 25 km or 50 km routes with full support, night markings and medical cover.

Run the Vanguard Way Marathon or Half on 2 August 2026 from Croydon along scenic Surrey and Sussex woodlands and ridges. Finishers receive a medal plus a goody bag with a race t shirt and snacks.

Take on the MTC Thames Challenge, a four day 184 mile multi stage endurance race along the scenic Thames Path from the source to the Thames Barrier. Included hotels and main evening meals connect the stages for a supported ultra experience.

Tackle the MTC Cotswold Ultra, a scenic 57 mile point to point along the Thames Path from Kemble to Oxford, with a bespoke medal and MTC head visor for all. Classic Cotswold views and trophies for winners make this a memorable challenge.

Take on the MTC Oxford Ultra, a 49 mile point to point along the Thames Path from Oxford to Henley. Expect scenic riverside trails, three support checkpoints and challenging self sufficient ultrarunning with a bespoke finisher medal.

Scenic 7 hour timed run along the River Thames on 7 Aug 2026 lets you choose any distance from 3 km to ultra. Finishers get medals and distance pins, with aid stations, cafe and vegan goody bags.