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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.

November 2026
Multi terrain 5K and 10K trail races in Radnage, Chiltern Hills, raising funds for the village school and including a one mile children's fun run.
A 7-hour time-challenge along the River Thames in Staines with flexible distances from 3 km up to 50 km, themed medals, distance pins, goody bags and aid stations.
A roughly 9 mile trail race around Avebury, Wiltshire, over mixed terrain with chip timing; proceeds support Wiltshire and Bath Air Ambulance.
A riverside trail run from Alexandra Gardens in Windsor with two measured routes, riverside landmarks, chip timing and a finisher medal.
A 10 km single lap route at Long Valley featuring mud, marshes, steep climbs and named water features; a 5 km option was added in 2022.
A 7 hour Time Challenge along the River Thames offering flexible distances from 3km up to 50km, with medals, distance pins and aid tables.
A guided 10 km trail run around the Devil's Punchbowl in Hindhead with group pacing, headtorch night options and equipment trials.
A timed 21 km trail run at Farleigh Wallop Estate on 28 November 2026 with cupless water stations, medics, onsite parking and a sustainable finisher medal.
A guided 30 mile trail run from Haslemere on the Serpent Trail and Sussex Border Path, led by an experienced ultra runner at a social group pace.
A 7 hour Time Challenge in Staines offering flexible lap distances, themed medals, goody bags and Krispy Kreme donuts at the finish.
Trail races at Mapledurham Estate in 2026 with 10K, 10 mile and half marathon courses across muddy paths, woods and estate roads and postrace refreshments.
Watlington XC 10k is a 10 km cross country fell run over the Ridgeway and Chiltern Hills for runners aged 16 and over, with pre-registration required and no entries on the day.
December 2026
A timed challenge along the River Thames in Staines offering distances from 5 km up to 50 km with a medal, bobble hat and on-course aid.
Winter marathon and half marathon across Salisbury Plain with marked trails, stocked checkpoints, on course safety support and finisher medals.
A festive community run at Frimley Lodge Park on 6 December 2026 with a new mostly flat course, 5K and 1K Fun Run, Santa hats and medals.
A festive 7 hour time challenge along the River Thames with distances from 3 km to 50 km, medals, goody bags and on-course aid.
An offroad multi-lap event at Shalford Park, Guildford offering runs from 3.14 to 31.4 miles, a Pi marathon option, a 1-mile kids run, and bespoke Pi Pie medals.
Christmas themed timed run at Coate Water Country Park with 3.28 mile laps, oak medals and an aid station offering vegan and gluten free options.
Join a festive Christmas run along the flat Jubilee River. Choose your own distance in this 6-hour timed event on a scenic towpath. All finishers receive a bespoke festive medal.
A 10 km trail run on the Yattendon Estate at Renegade Brewery on December 24th, with a Canicross category, medal, pint cup and a mince pie for finishers.
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