Trail Running calendar near Winchester 2026-2027

We have found 400 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

Event Format The Purbeck Hill Challenge is a one-day long-distance walk or run event on public rights of way, featuring orienteering sections. Participants must navigate to various checkpoints. There is a mix of navigation using a standard..

Celebrate Valentine's Day with riverside laps along the scenic Thames at Xcel SPORTS HUB. Choose 5k to ultra, run as many laps as you like within a one hour start window and 7 hour limit, and earn a bespoke finisher medal.

Multi-distance trail event in Dalwood, Axminster on 15 February 2026 with 10 mile, 5 km and 3 km routes across muddy, hilly countryside. Village Hall is race HQ with parking, toilets and on-site medical support.

Take on the Hot Lips Run at Crystal Palace Park and choose how many 1.65 mile laps to tackle, from 5k to ultra, on scenic off road trails with rolling hills. Timed with a 7 hour limit and a finisher memento for all entrants.

Join Phoenix Running West Sussex for the Violets Are Blue Valentines Run at Southwater Park. Pick distances from 5 km to ultra, lap the flat compact trail at your own pace with rolling starts and claim a blue Love Spoon medal.

Run a flat, traffic free 10k on the National Cycle Network from Calne to Stanley near Chippenham, chip timed and well marshalled on an out and back multi terrain course. A 1 mile fun run for under 17s and limited entries make this a friendl..

Run Brimscombe's canal towpath at the Back to the 80s timed event, choosing any mix of 2.62 mile laps to make 5k to ultra distances. Enjoy a relaxed one hour start window, seven hour limit and a bespoke finisher medal to mark your effort.

Riverside races at Wraysbury Skiff & Punting Club near historic Runnymede. Marathon, half marathon and 10 km run on flat out and back laps along the Thames with marked turnarounds, check points and chip timing.

Looped trail and road races in Chalfont St Peter where runners choose on the day between 7k, longer loops, marathon and ultra marathon distances with aid, pacing and crew support.

A set of city-centre races in Bath that run through two long lit tunnels under the city, with distances from Colourburst fun runs up to a 50 km ultra. Brickfields Park is the hub and the event supports Sustrans with a donation per runner.

Single lap trail races in the Meon Valley from Queen Elizabeth Country Park offering 16 mile, marathon and 50km options with marked routes, aid stations and mandatory fluid carriage.

The Winter Trail Run returns for its fifth year at Gatton Park. Choose between a 5k or 10k multi-terrain loop on the day. The event includes a Canicross wave, on-site amenities, and supports The Gatton Trust Charity.

A 50k trail on the North Downs Way from Denbies Wine Estate, covering 2986 ft of ascent with four aid stations and a 10 hour cut off. The fully signed route includes a woodland loop at Norbury Park and a wooden finisher medal.

UTMB Index

The Terminator 2026 is a tough but rewarding 12 mile trail race around Pewsey, Wiltshire, mostly off road with muddy climbs and high point views. All finishers receive a unique T shirt and race village treats await.

Trail and canicross races at Gatton Park on 22 February 2026, with 5K and 10K multi-terrain loops, chip timing, marshals, on-site parking, bag drop and medals for both humans and dogs.

Guided 10 km trail runs at Thursley National Nature Reserve in Surrey on 25 February 2026 and 7 July 2026. Flat group routes include a boardwalk section, headtorches for night runs and a car park; cost £16 per person.

G3 no.3 is a running event at Newlands Corner, Guildford on 28 February 2026 offering 10 km and 15 km distances with paid entry and entries closing on 26 February.

Guided 30 mile trail run from Harting Down along the South Downs Way, visiting Beacon Hill, Cocking Down and Kingley Vale. Presented as suitable for first time ultra runners, run at a group pace with practical support and route guidance.

Three waymarked trail routes on 28 February 2026 around Lulworth Cove near Wareham, with coastal views, varied terrain and aid stations. Mandatory kit is spot-checked and rolling cutoffs apply, with a 12 hour overall limit.

UTMB Index

Chocothon is a friendly timed lap on a flat 5.3 km riverside towpath, letting you complete as many laps as you can within a seven hour window. Distances from 5 km to ultra, medals and aid stations make it perfect for all abilities.