Logo

Winter Woolly 10km

Upper Woolhampton, United Kingdom • 24 Dec 2025

The Winter Woolly 10km is a popular trail running event held annually on December 24th at Elstree School in Upper Woolhampton, Berkshire. Now in its sixth edition, the race features a scenic multi-terrain course covering 10 kilometers with 80% off-road paths, including lanes, footpaths, trails, woodlands, and some hills, offering stunning views of the rural countryside. The event includes a separate Canicross 10km race and is a cup-less event with no water stations on the course. Participants enjoy chip timing, medals, mince pies, mulled wine, prizes, and free race photos. The race has a friendly festive atmosphere and ample facilities such as toilets, parking, and bag drop. Visit the organization's website for the most recent information.

United Kingdom South East (England) Upper Woolhampton

Race information

Website
10 km
114 m+
Visit the organization's website for the most recent information.
Trail runs nearby

Blended Trails - Backyard Ultra

New Alresford - 22 mi from Upper Woolhampton

The Blended Trails - Backyard Ultra will take place in New Alresford on Saturday 30 August 2025.

Henley River Half Marathon

Henley-on-Thames - 14 mi from Upper Woolhampton

Henley River Half Marathon, 10k & Juniors August 2025 is a RunThrough UK event held in Henley-on-Thames, UK. The course offers a fast scenic trail around Henley-on-Thames, starting and finishing by Temple Island Meadows, the official start line for the Royal Henley Rowing Regatta. Distances availabl..

Andover Trail Marathon

Enham Alamein - 17 mi from Upper Woolhampton

The Andover Trail Marathon, held in North Hampshire at Kings Road, Enham Alamein, offers both a full marathon (26.2 miles) and a half marathon (13.1 miles) through scenic trails. The marathon route follows the Testway up to Coombe Gibbet, Hampshire's highest point, then returns via the Conholt estat..

Hackpen Hill Trail Run

Uffcott - 28 mi from Upper Woolhampton

The Hackpen Hill 10k Trail Run is an annual off-road event held near Weir Farm, Broad Hinton, Swindon, Wiltshire. Celebrating its tenth year, the race features a challenging one-lap course that traverses farm tracks, fields, mud, and rolling hills alongside the historic Ridgeway trail. Suitable for..

Bradenham Blast

High Wycombe - 23 mi from Upper Woolhampton

Bradenham Blast is a trail running event in the Chiltern Hills at Manor Farm, Bradenham, near High Wycombe, UK. Boondock Events offers 5km, 10km, and a new half-marathon for 2025. The courses are hilly, scenic, and suitable for many abilities, weaving through tranquil beech woodland and rugged trail..

SOX 10km

Ipsden - 11 mi from Upper Woolhampton

SOX 10km is a 10km multi-terrain race organized by Racing Line Running, taking place on September 7, 2025, starting and finishing at the South Oxfordshire Brewery taproom in Ipsden, Oxfordshire. The course blends private terrain, trails, woodlands, fields and local roads, with around 60% off-road an..