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 398 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
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 Halloween-themed 3 km obstacle run on a new course with waves of participants, mandatory headtorch, on-course burpee penalties, and optional costumes.
Night gravel running in Alice Holt Forest with 5 km laps offering 5, 10 or 15 km, one refresh outpost per lap and a cup free refill policy.
An evening Halloween trail at Hogmoor with kids, adult and canicross looped races, medals, free parking 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.
Halloween-themed Time Challenge in Staines along the River Thames with distances from 3 km up to 50 km and medals for finishers.
Halloween themed Backyard Ultra at Meoncross School: repeat 6.7 km out-and-back laps until one runner remains, with free parking, indoor access and medals for all.
November 2026
Coastal 15.3k, 10k and 5k runs along West Wittering Beach with sea views, chip timing, on course water and a finisher medal.
Autumn trail races at Wendover Woods offering Marathon, Half Marathon, 10k and Junior Run on hilly, multi-terrain loops with on-site facilities and a six hour cut off.
Event Seven of the Wacky Races series is a seafront running event on 1 November 2026 at The Shack, Lee-on-the-Solent with 5K, distance-building options and a 6-hour challenge.
Two days of marathon and half marathon races around Caldecotte Lake in Milton Keynes on 6 and 7 November 2026, with multi-lap clockwise courses, on-course water and toilets, enforced time limits, and bespoke finisher medals.
Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.
A remembrance midweek run by Saturn Running in Staines upon Thames offering multiple distances and a poppy finisher medal along the River Thames.
Trail routes of 21.3K, 16.5K and 12K from Goodwood Racecourse through the South Downs with varied terrain, views and on-course support.
Night trail at Stonor Park with three marked routes of 7 km, 13 km and 17 km, timed results, one outpost on middle and long routes and no dogs allowed.
Trail races of 7 km, 13 km, and 22 km through Stonor Park and the Chilterns, with steep sections, marked courses, and outpost support.
Nighttime trail run around Winchester on signed routes including the South Downs Way, offered in 12 km and 22 km options with mandatory headtorches.
76km ultramarathon or 36km run or walk finishing at Portsmouth Historic Naval Dockyard on 7 November 2026.
A 27 mile night group training run at Devil's Dyke with about 1,000 m of ascent, led by Trail Run Explorers; head torches required and participants must be 16 plus.
Trail event in Windsor on 8 November 2026 with chip timed 10K and half marathon from Alexandra Gardens, featuring medals, free photos and an event village.