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 397 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
Trail races at Bedgebury Pinetum on 18 October 2026 offering a half marathon, 10K and a junior race on 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 along the Thames Path from Iffley to Henley on Thames with five aid stations, GPS tracking, mandatory kit and a progressive 11.5 hour cut-off.
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, themed medals and distance pins, an aid table, goody bags including a vegan option, and on the day number collection.
Hip-hop themed coastal out-and-back at Milford on Sea with self-chosen distances from 5K to ultra and 5.3 km laps, cupless aid stations and sea views.
Off road marathon and half marathon south of Canterbury with live tracking, checkpoints, mandatory kit lists, event HQ facilities, and a charity donation from entries.
Looped events where runners choose how many laps to run on the day, with maps, aid stations every lap and distances from 5K to 50K across several venues.
Social 8 km trail run with North Downs views, finishing at Greyfriars Vineyard for lunch, a glass of English sparkling wine and a guided tasting.
Free biweekly Sunday morning trail runs from Surrey Trek and Run with multiple distances and a limit of 10 participants per leader.
Guided trail run at Box Hill with approx 14 km or 18 km routes, free for up to 50 runners and including guided group running, giveaways and post-run food.
A 7 hour time challenge along the River Thames in Staines with flexible distances, chooseable medals, on course aid and goody bags.
An overnight self supported 50 km ultra from East Grinstead to Brighton on 30 to 31 October 2026, in person event with tickets at £14.46 and no refunds.