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Trail Running Calendar near Hadleigh, Benfleet 2026-2027

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Explore the top trail runs near Hadleigh, Benfleet for 2026-2027! We've gathered 68 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

December 2026
An evening self navigation trail of about 6 miles from The Compasses in Littley Green with a secret destination, cryptic clue bonuses, refreshments and entry vouchers.
A social 12k run on 19 December 2026 with a GPX/Strava route, brewery and finish bar drink tokens, festive medals and a post-run rum option.
A 50 km trail ultra along the North Downs Way from Detling to Wye with about 1,000 m of ascent, three checkpoints and mandatory kit requirements. The route passes Boxley Warren, Thurnham Castle, Lenham Cross and the Wye Downs.
20 Dec 2026 at Abberton Reservoir Visitors Centre: repeat just over 5 km laps in a timed up to six hour challenge, with medals and proceeds to Essex Wildlife Trust.
Navigate an 11 mile circular trail between Maldon and Mundon using written instructions on a course that is 95 percent off road.
Boxing Day event at Friday Woods where runners and cyclists race off-road for the Markham Cup, with junior and senior lap distances.
A winter trail 10k at Trifarm in Boreham on 27 Dec 2026, mostly off road on public footpaths and bridleways and serving as the final race of a four-round series.
A self-navigation trail race at The Prince of Wales, Stow Maries offering 6 or 11 mile routes with a £4 pub voucher included and age restrictions in place.
January 2027
A narrative trail marathon around Danbury with 95% off-road terrain, three checkpoints, finishers' medal and hot food, based at East Hanningfield Village Hall.
County cross-country championships at Gloucester Park, Basildon on 9 January 2027 with races from U12 to Senior Men and team medals.
A 15 mile multi terrain trail race at Hadleigh Country Park with muddy hills, seaside sections and Thames Estuary views; cupless water stations require a reusable cup.
February 2027
Lapped running on the Flitch Way at Rayne with 5.3 km loops, multiple distances, an aid station every lap and a bespoke medal and goody bag.
A 42-mile trail race from Chipping Ongar to the ancient Chapel of St Peter-on-the-Wall, following an old pilgrimage route through rural Essex. Mostly off-road and often muddy, the route is waymarked with GPX support, four outdoor checkpoints and mand..
A single lap undulating 10k trail race at Hadleigh Country Park with steep hills, deep mud, technical terrain and mandatory trail shoes.
March 2027
Sevenoaks Circular Challenge on 14 March 2027 offers three new routes of 14, 20 and 30 miles with indoor checkpoints and catering; the 30 mile route has 4200 ft ascent and an 11 hour limit.
Looped, timed runs at Ranscombe Farm Nature Reserve on 14 March 2027 offering distances from 5 km to ultra with medal and a no medal entry option.
A PARAS'10 event in Friday Woods featuring a 3-mile woodland loop with one to three laps, offering run, TAB and canicross categories plus a 2-mile youth race.
A flat 10 km out and back along the river from Chartham to Canterbury with village-hall facilities, a finisher's medal and mixed feedback on mud, signage and marshals.
April 2027
Fifth Galloping Grind 10k trail run on 04 Apr 2027, held on a predominantly anti-clockwise Spring course with limited onsite parking and post-race hot drinks and cakes.
An evening 5 mile trail run from The Black Buoy pub in Wivenhoe on 06 April 2027 with route provided in advance and a tail walker on course.
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