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 404 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
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 run in Surrey finishing at Greyfriars Vineyard on the North Downs with fizz, food and a guided wine 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.
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 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.