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Trail Running Calendar near Upper Woolhampton 2026-2027

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Explore the top trail runs near Upper Woolhampton for 2026-2027! We've gathered 155 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Thames Valley LDWA challenge walk in Marlow on 4 October 2026 offering 25 km, 40 km and 50 km routes with checkpoints, mandatory kit and entry limits.
A 7 hour Time Challenge along the River Thames with flexible distances from a 3 km minimum up to ultra and 50 km options. Finishers choose a medal from past events and have access to aid stations and a goody bag.
Half marathon and 10 km races at RAF Greenham Common in Thatcham, Berkshire. The traffic free, flat course has water stations, free parking and a children's race paid on the day for £5; proceeds support New Life Special Care Babies.
A mixed-terrain 10 km and 5 km race around Frieth in the Chiltern Hills featuring woodland paths, country roads and notable climbs.
Community-supported trail runs at Old Basing offering 10K and 6K chip timed races plus a 2K fun run to raise funds for local schools.
Flat mixed trail races along the Basingstoke Canal and through Wellesley Woodlands with 10 km, 5 km and a 2 km fun run, chip timing and a collectable medal.
A 100 mile trail race from Goring and Streatley using the Thames Path and Ridgeway in four 25 mile out and back spurs, with 16 aid stations and a 28 hour cutoff.
Trail and multi terrain races at Dummer Down Farm on October 17 include a 10 km, a Canicross 10 km and a two lap half marathon with finishers' pint and camping option.
A 47-mile point-to-point ultra from Iffley to Henley-on-Thames along the Thames Path with five aid stations, mandatory kit checks and live GPS tracking.
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, themed medals and distance pins, an aid table, goody bags including a vegan option, and on the day number collection.
Social 8 km trail run with North Downs views, finishing at Greyfriars Vineyard for lunch, a glass of English sparkling wine and a guided tasting.
Night gravel runs in Alice Holt Forest offering 5 km, 10 km or 15 km on marked laps with one outpost per lap and parking on site.
Evening Halloween run at Hogmoor with kids and adult looped races, muddy sandy terrain, canicross, fancy dress and a medal for every finisher.
A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.
Halloween-themed Time Challenge in Staines along the River Thames with distances from 3 km up to 50 km and medals for finishers.
November 2026
Timed multi lap run at Coate Water Country Park with 3.28 mile laps, finishers receive a medal and the event supports the British Legion.
A seven hour timed event in Staines upon Thames on 6 Nov 2026 offering distances from 5 km to ultra, a poppy finisher medal, and on-course aid with vegan options.
Night trail running at Stonor Park with three route distances, outposts on middle and long courses, no dogs and a cup-free outpost policy.
Three trail distances through Stonor Park and the Chilterns with marked courses, fuel outposts, on site facilities and notable gradients.
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