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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 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.
A 7 hour time challenge along the River Thames in Staines with flexible distances, chooseable medals, on course aid and goody bags.
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.
An evening Halloween trail at Hogmoor with kids, adult and canicross looped races, medals, free parking and on-site refreshments.
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.
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.
A torchlit trail run from Winchester Athletics Track with 12 km and 22 km options across the South Downs Way and local trails. The course is fully marked; headtorches and at least 500 ml of fluid are required.
76km ultramarathon or 36km run or walk finishing at Portsmouth Historic Naval Dockyard on 7 November 2026.
A licensed 7 hour Time Challenge in Staines along the River Thames with multiple distances from 3 km to 50 km, commemorative medals and distance pins.
A commemorative 7 hour Time Challenge in Surrey along the River Thames with options from 3 km up to 50 km, medals, distance pins and on-course aid.
Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.
A multi-terrain 5K and 10K race in the Chiltern Hills on 15 November 2026, organised by the Radnage Primary School PTA, with water stations, first aid, a village hall cafe and proceeds supporting the school.
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