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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 136 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Trail races at Amport Cricket Club with 5k, 10k, 10 mile and canicross on marked multi-terrain routes, cupless stations, first aid and finish-line refreshments.
Trail event near Marlow offering Half Marathon, 10K and a 1K fun run with chip timing, medals and on course water stations.
A mixed terrain 10 km race across the grounds of Highclere Castle on 27 September 2026 supporting Thames Valley Air Ambulance and Newbury AC.
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.
Scenic half marathon and 10KM at RAF Greenham Common, family friendly and supporting 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.
A MacTuffX fitness racing event in Swindon on 11 October 2026 offering solo, doubles and relay formats over 10x400m and 10x800m with included t-shirt and medal.
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 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.
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.
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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