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

September 2026
A scenic 10K trail run through the historic grounds of Loseley Park on 6 September 2026, licensed under UK Athletics with official timing and finisher medals.
Free MHAC end of summer gathering at Dummer Down Farm with guided 3K, 5K and 8K trail runs, coffee, food, beer, live music and optional donations to Mind.
Experience a scenic trail marathon or half marathon through the Surrey Hills along the historic Pilgrims Way and North Downs Way.
Seven hour Time Challenge along the River Thames in Staines offering lap based distances from 3km to ultra, with medals, pins, aid stations and goody bags.
A single loop 50 mile race through the Chiltern Hills with 5600 ft of climb, five aid stations, full medical cover and a 13 hour cut off on 19 Sep 2026.
A countryside multi-terrain 10K in Longworth village with kilometer markers, water stations, a kids fun run, and entries limited to 200 runners.
A Henley basecamp trail event with looped options of 50 km, 25 km and 10 km, covered rest stops, GPS tracking, medical support, camping and finish-line hospitality.
Three community races at Harcourt Hill, Oxford on 26 Sep 2026 with 10 km, 3 km and 1 km options. The 10 km is mostly off road and includes a section of the Oxford Greenbelt Way; medals and prizes are provided.
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 run in Bisham, Marlow on 27 September 2026 with Half Marathon, 10k and 1k routes along the Thames and through woodland.
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.
Walking routes of 25 km, 40 km and 50 km around the Hambleden and Stonor valleys from Marlow with checkpoints, on-route food and a finish badge.
Scenic half marathon and 10KM at RAF Greenham Common, family friendly and supporting New Life Special Care Babies.
Road and trail races in the Chiltern Hills on 11 October 2026 offering 5 km and 10 km routes with woodland paths, country lanes 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 functional fitness race in Swindon combining ten Xercises and repeated runs with solo, doubles or five person relay options for entrants aged 18 and over.
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 on the Thames Path and Ridgeway, run as four 25 mile out and back legs with 16 aid stations and a 28 hour cut off.
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.
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