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.
May 2027
Inflatable obstacle-course event at Brands Hatch on 15 May 2027 with 2.5k to 15k lap options, music zones, family entries and finishers' medals.
A 10th anniversary half marathon and new 10k in Chislehurst that explores local green spaces and raises funds for The Maypole Project.
Trail races of 10 mile and 5 mile at Cammas Hall Farm, Essex on 16 May 2027 with chip timing, water stations and finisher t-shirt and medal.
June 2027
A 27 mile evening trail marathon near Purleigh across saltmarsh, towpaths, vineyards and woods, with a 6.5 hour cutoff and a field limited to 50 runners.
A point-to-point 50 km trail race along the River Medway from Rochester to Tonbridge with a predominantly flat course, four aid stations and a 9 hour cut-off.
A point-to-point 30 km trail along the River Medway from East Farleigh to Tonbridge with three checkpoints, chip timing, bag transfer and an athletics track finish.
A 10 km out-and-back race through gravel paths and woodland at Weald Country Park in Brentwood, organised by MCC Promotions. The event includes on-day registration, water stations, prizes and supports the charity Sport In Mind.
Timed trail weekend at Leybourne Lakes with a fully marked 2.5 km loop and 6, 12 and 24 hour solo and relay options plus race village facilities and live timing.
Annual not for profit run organised by Istead & Ifield Harriers from Cyclopark through the Kent countryside with proceeds supporting local charities.
July 2027
An 82 mile point-to-point ultramarathon from Epping to Harwich along mixed trail and road, with checkpoints, GPS tracking, a race medical team and a 24 hour cut-off.
A muddy 5km obstacle run at Wild Forest in Brentwood on 3 July supporting Essex Wildlife Trust, with safety teams, parking, showers and a medal for each participant.
A 24 hour multi terrain relay or solo race at Albyns Farm with teams of two to eight running repeated 5.75 mile laps and onsite camping and facilities.
Pretty Muddy 5k at Hylands Park Chelmsford on 18 July 2027 is a grass obstacle course with climb crawl and slide elements, staggered wave starts and a minimum age of 13.
August 2027
A navigational trail event near Little Baddow, Essex with a roughly 14 to 18 mile route, team entries of two or three, waterproof maps provided and mandatory compass and phone.
Inflatable obstacle laps at Hylands Park Chelmsford on 7 August 2027 with 2.5 km to 15 km options, music zones, medals and on course water.
A Backyard Ultra at Cut Hedge Park where runners complete a 4.167 mile loop each hour until one athlete remains, with camping and on-site facilities.
Experience a scenic 10k trail run through Shoreham Woods in Kent featuring chip timing and a dedicated Canicross category for runners with dogs.