Upper Woolhampton
Trail Running Calendar near Upper Woolhampton 2026-2027
Explore the top trail runs near Upper Woolhampton for 2026-2027! We've gathered 122 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
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 at Renegade Brewery on the Yattendon Estate. The course is mostly off road with one water refill station and finishers receive a medal, a pint cup with a free drink and a mince pie.
A traditional 3.5 mile Boxing Day run around Hindhead commons and the Devils Punch Bowl, with Mens, Ladies and a Drinking Run category. All profits support Holy Cross Hospital.
A winter cross-country event at Butlers Lands Farm featuring water crossings, Roman Walls, fields and footpaths. Distances are 10K and 10 Mile with entry fees from £32 to £35; finish-line refreshments include mulled wine and mince pies.
January 2027
A flexible seven hour time challenge on a signed Thames riverside loop with distances from 3km to 50km, medals, pins and goody bags.
Trail run near Winchester on 10 January 2027 with 21.4k and 12.1k routes around Farley Mount, chip timing and finishers medals.
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.
A seven hour time challenge along the River Thames with distances from 3km to 50km, medals and pins, mixed path and trail terrain.
A two day 66 mile winter trail event on the North Downs Way with marked routes, staffed aid stations, overnight accommodation and luggage transfers.
A 30 mile non-competitive group trail run from Harting Down along parts of the South Downs Way, passing Beacon Hill, Cocking Down and Kingley Vale. Led by an experienced guide and recommended for those who have run at least 22 miles in training.
March 2027
A 10 km mixed-terrain run from Windsor & Eton Brewery along towpaths and parkland, with staggered starts, a pint cup and free drink at the finish, chip timing and downloadable race photos.
A 24 hour endurance format at Alice Holt Forest where runners repeat a 6.7 km loop each hour, finishing laps within 60 minutes. Wooden medals are given to finishers and a wooden trophy is awarded to the overall champion.
A 50km trail ultramarathon through the Chilterns centered at Stonor Park, run as two 25km loops with 4000 ft of climb, five aid stations and full medical support. The event has a nine hour finish limit and medals for all finishers.
Point to point trail races on the South Downs Way offering a 50 mile ultra, a 50 km ultra and a marathon with marked routes, aid stations, coach transfers and an option to plant a tree instead of taking a medal.