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 363 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 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, course marshals, prizes and tea and cake after the race at the village hall.
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.
Coastal out and back run at Milford on Sea with a hip hop theme, flexible starts and distance choices from 5K to ultra marathon.
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.
A social 8 km trail run on the North Downs from Greyfriars Vineyard, finishing with lunch, a glass of English sparkling wine and a guided wine tasting.
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.
A relaxed night obstacle run at OPP over two 1.5 km laps, with technical obstacles, surprise elements and a strict headtorch requirement.
Night trail laps in Alice Holt Forest on 5 km circuits with 5 km, 10 km or 15 km options, one outpost per lap, free parking and no dogs allowed.
An evening Halloween run at Hogmoor with kids, canicross, 6.6 km and 10 km options, fancy dress encouraged, medals for finishers and on‑site refreshments.
A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.
Endurance loop event at Meoncross School on 31 October to 1 November 2026 where runners complete repeated 6.7 km out and back laps until one runner remains, with free parking.
November 2026
Coastal runs on West Wittering Beach with sea and downs views, chip timing and three distances: 15.3 km, 10 km and 5 km, plus on-course support and a finisher medal.
Trail races in Wendover Woods on hilly, multi terrain forest loops with marathon, half marathon, 10 km and a junior run plus on site amenities and parking.
Seafront running event at Lee-on-the-Solent on 1 November offering a 5K, distance-building options and a 6-hour challenge; entry £20 and 100 places available.