Upper Woolhampton
Trail Running Calendar near Upper Woolhampton 2026-2027
Explore the top trail runs near Upper Woolhampton for 2026-2027! We've gathered 130 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A guided 30 mile trail run from Haslemere that follows sections of the Serpent Trail and Sussex Border Path, aimed at runners attempting an ultra for the first time. Group pace, varied terrain, cost £55.
Trail running at Mapledurham Estate on 29 November 2026 with 10 km, 10 mile and half marathon routes across muddy paths, woodland and fields.
December 2026
A hilly woodland trail race of 10 km around Hughenden Manor near High Wycombe, fully marked with a water stop at 5.3 km and a GPX route available.
A winter trail event on Salisbury Plain offering Marathon and Half courses, marked routes, stocked aid stations, marshal support and on-route medical cover.
Mince Pi Run on 13 December 2026 at Shalford Park, Guildford offers looped offroad races from 3.14 to 31.4 miles, a Pi marathon option and a one mile fun run shaped like the Pi symbol. The course runs along the water and results are posted online.
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 timed festive event on the Itchen Way in Winchester with flexible rock up start times, a measured out-and-back course, lap options up to ultramarathon distance, and a bespoke finisher medal.
A 10 km trail run and Canicross 10 km on December 24th around Yattendon Estate with hilly woodland trails, a medal, mince pie and a pint cup included.
Trail event at Butlers Lands Farm with water crossings, Roman Walls and fields, offering 10K and 10 Mile options plus finish line mulled wine and mince pies.
Off road races at Longmoor across sand dunes, ponds and mud with single and two lap options and medals for all finishers.
January 2027
A riverside 3.28 miles out-and-back event at Wraysbury offering distances from 5K to ultra and a six hour challenge, licensed by TRA and run under UKA rules.
Timed out and back event on The Itchen Way in Winchester with flexible starts, lap distances from 2.62 miles up to ultra distance, and on-course vegan options.
A winter trail run near Winchester with two off-road routes around Farley Mount, chip timing, on-course support and a finisher medal.
A flexible 7 hour time challenge along the River Thames in Staines offering distances from 3 km up to 50 km, medals, distance pins and on-course aid.
Scenic winter trail run in Windsor offering 10K and half marathon distances, with chip timing and proceeds supporting Brain Research UK.
February 2027
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.