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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
A 7 hour Time Challenge on a signed riverside loop in Staines offering flexible distances from 3 km up to 50 km, with medals, distance pins, aid stations and goody bags.
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.
Trail and fun runs near Old Basing on 11 October 2026 with chip-timed 10K and 6K races plus a 2K family fun run supporting 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 race at Dummer Down Farm offering 10 km, canicross 10 km and a half marathon with mainly off road terrain and a pint cup plus a free drink included.
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.
A social 8 km trail run on the North Downs from Greyfriars Vineyard, finishing with lunch, a glass of English sparkling wine and a guided wine tasting.
Night trail laps in Alice Holt Forest on 5 km circuits with 5 km, 10 km or 15 km options, one outpost per lap, free parking and no dogs allowed.
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.
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