Southend-on-Sea
Trail Running Calendar near Southend-on-Sea 2026-2027
Explore the top trail runs near Southend-on-Sea for 2026-2027! We've gathered 64 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Experience the historic trails of Kent with 25km, 50km, or 100km races featuring scenic woodlands, castle views, and a festival style race village.
Team cross country relays at Chingford Plain on 19 Sep 2026 with junior, senior and veteran races, limited entries and specific England Athletics eligibility and team rules.
A five mile trail run on 24 September 2026 at The Viper in Mill Green near Ingatestone. Limited to over 18s with a small field; participants must be self sufficient with phone and headtorch and a tail runner is on course.
October 2026
A 25 km EcoTrail event in Bell Common, Epping on 3 October 2026, listed as part of the 2026 events calendar.
Chelmsford Brew Co hosts a one-off 10 km trail run and a relaxed hike on 03 Oct 2026, with a finishers drink, crisps and a medal.
A 50 mile coastal ultramarathon along the Essex saltmarshes, starting at South Woodham Ferrers Rugby Club and finishing at Maldon Promenade Park. Fully supported with aid stations, GPX route files, a shuttle option and a 15 hour cut off.
Looped trail event near Maidstone offering 50 km, 25 km and 10 km options. The route follows the North Downs Way and River Medway and includes covered rest stops, GPS tracking and camping at basecamp.
Trail Half Marathon and 10K in Epping Forest, London on 10 October 2026 with marked routes, chip timing, eco measures, and limited parking.
A single-lap 10K on 11 October 2026 around Burnham on Crouch, featuring sea wall coastal paths and countryside trails. The event is based at Dengie Hundred Sports Centre with free parking, facilities and post-run food and drink.
An evening tarmac trail of about 6 miles in Chelmsford with a written route, glow in the dark medal, limited places and on site parking and facilities.
A timed self supported anti clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre with a staffed pub check at 10 km.
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.
A Halloween themed 6.66 km trail run in Chelmsford on 31 October 2026 with GPX/Strava route support, fancy dress prizes and a brewery finish offering a medal, drink and crisps.
November 2026
Experience an after dark Halloween themed multi terrain run through Leigh on Sea featuring 10k and 5k routes with chip timing and finisher medals.
A November muddy obstacle event in Brentwood Essex with 6 km, 12 km and 24 km plus options across farmland, woods and lakes featuring 40 to 200 plus obstacles.
A Remembrance Sunday trail event in Brightlingsea on 8 November 2026 with live Last Post and a two-minute silence during the race. A looped course offers 10km, half, marathon and a six hour timed option with on-course aid stations.
Experience the longest established trail race in Essex with a self navigated course of 6 or 16 miles starting from a traditional pub in Chelmsford.