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 67 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 10K run through the private parkland and tree lined avenues of Chevening Estate in Sevenoaks, combining estate heritage, timed results and official photography.
A charity trail run from The Zach Willsher Pub in Benfleet offering two undulating routes of about 5.7 miles and 12 miles, with written route instructions and timed entries. Funds raised go to Macmillan and finishers receive a pub voucher.
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.
An autumn running event at Foxes Farm, Colchester on 27 September 2026 offering 10K, 5K and a 1K family dash over traffic-free farm tracks and past pumpkin fields, with chip timing, medals and an event village.
October 2026
London EcoTrail 25 km is a trail running event in Bell Common, Epping on 03 Oct 2026. It is organised by London based ultramarathon event company Camino Ultra as part of their 2026 events.
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.
A half marathon and 10K through Epping Forest, London on 10 October 2026, run on marked woodland trails with aid stations, chip timing and an eco friendly focus.
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.
Approx 6 mile self navigation trail in Chelmsford with glow in the dark medals and light refreshments, limited to 120 places; minimum age 16.
A timed, self supported anticlockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre. The mostly coastal route includes sea wall, grass and gravel paths, a 10k pub check point and a four hour cut off.
Trail marathon and half marathon near Canterbury through Kentish countryside; marathon requires navigation and both races use CCCU Sports Centre as HQ.
A countryside walking event from Blackmore with a 26 mile figure of eight route and an 18 mile option, forming part of the Essex and Herts Triple Challenge.
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
An after dark multi terrain 10 km and 5 km event in Leigh on Sea with chip timing, mandatory headtorches and sustainably sourced finishers medals.
A November muddy obstacle event in Essex offering 6 km, 12 km and 24 km+ courses with natural and man‑made obstacles including a Deathslide and zip wire.
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.