South East (England)
Trail Running Calendar South East (England) 2026-2027
Explore the best trail runs in South East (England) for 2026-2027! Our updated list features 395 exciting trail runs across the region. Find your next trail run in South East (England) below and join the trail community at these great events!
October 2026
A mixed-terrain 10 km and 5 km race around Frieth in the Chiltern Hills featuring woodland paths, country roads and notable climbs.
A single lap 10 km trail race through Limpsfield Common and the High Chart, mostly off-road with varied slopes, a water station at about 5.5 km, and finisher T-shirt and medal.
Community-supported trail runs at Old Basing offering 10K and 6K chip timed races plus a 2K fun run to raise funds for local schools.
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 10 km undulating multi-terrain race from Buckingham Town Centre through Stowe National Trust gardens and countryside, with medals for finishers and local charities supported.
Wacky Run Six in Fareham on 11 October is a themed run with an Army Surplus Special atmosphere, a six hour personal-distance format, themed medals and limited entries.
Biweekly free Sunday morning trail runs from Surrey Trek and Run with varied routes and distances, limited to 10 places per leader.
A lap based Friday timed run on a flat 5.3 km out and back course along the river Thames, with distances from 5 km up to ultra. Both attended and virtual entrants receive a finisher medal.
A 100 mile trail race from Goring and Streatley using the Thames Path and Ridgeway in four 25 mile out and back spurs, with 16 aid stations and a 28 hour cutoff.
An annual 25 km or 50 km countryside challenge in Kent Surrey and Sussex with written route directions, checkpoints, included food and GPX files.
Trail and multi terrain races at Dummer Down Farm on October 17 include a 10 km, a Canicross 10 km and a two lap half marathon with finishers' pint and camping option.
Trail races at Bedgebury National Pinetum & Forest on 18 October 2026, offering half marathon, 10 km and junior distances on traffic free woodland trails.
Off road cross country race of about 6 miles around Manor House Farm in Hardwick, with water crossings, limited to 300 runners and minimum age 17.
A 10 km trail run through the private grounds of Hole Park, a historic estate near Cranbrook, Kent, on 18 October 2026. Entry is priced at £25 and the event includes timed results, finisher medals and official race photography.
Trail event in Fernhurst with a 10 km route to Temple of the Winds and a shorter 4.5 km adult trail, licenced by the Trail Running Association.
Trail runs of 10 km and 5 km around Blackpit Brewery on October 18 2026, using private multi terrain trails through woodlands and estate tracks. Entrants receive a medal, a pint cup and a free drink at the finish.
Timed multi-lap running at Buchan Country Park in Crawley with lap based distances from 5 km up to ultra, flexible start times and a seven hour time limit. Medal and lower cost no medal entry options are offered.
An 8 km trail loop around Herstmonceux with over 70% trail, prizes for first male and female, village hall facilities and a 60 person entry limit.
A trail running weekend at Beachy Head offering Ultra, marathon, half and 10k distances with coastal scenery, staffed aid stations and marked routes.
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.