Sittingbourne
Trail Running Calendar near Sittingbourne 2026-2027
Explore the top trail runs near Sittingbourne for 2026-2027! We've gathered 53 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
Looped trail event from Maidstone with supported 50 km, 25 km and 10 km routes, covered rest stops, camping and on course medical support.
Military style obstacle mud run at Hever Castle Kent with 3 km, 6 km and 12 km options and many obstacles modelled on Royal Marines training.
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.
Trail races at Bedgebury National Pinetum & Forest on 18 October 2026, offering half marathon, 10 km and junior distances on traffic free woodland trails.
A 10 km trail run through the private grounds of Hole Park, a historic estate near Cranbrook, Kent, on 18 October 2026. Entry is priced at £25 and the event includes timed results, finisher medals and official race photography.
Timed, self supported anti clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre, with a pub check point about 10k in and a four hour cut off.
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 5 km night trail run at Langdon Nature Discovery Park with glow sticks plus a free 800 m Little Monsters children's trail, raising funds for local charities.
A Halloween brewery trail run in Chelmsford with a devilish 6.66 km route, fancy dress rules, a finishers medal and limited places.
November 2026
An after dark multi terrain 10 km and 5 km run in Leigh on Sea on 1 Nov 2026 with chip timing, themed medals and support for local charities.
Muddy obstacle runs in Brentwood, Essex offering 6 km, 12 km and 24 km plus options across farmland, woods and lakes with dozens of natural and man made obstacles.
A self-navigation trail race on paths, tracks and country lanes with approx 16 and 6 mile routes and a different course each year.
A 6.66 mile woodland trail run at Kings Wood near Ashford featuring muddy, hilly and technical sections, limited to 200 runners and organised by Ashford Tri Club.
An 8.5 km mostly trail loop around Northiam with a marked and marshalled course, prizes for first male and female, and entry limited to 60 runners.
December 2026
A hilly five mile trail race in Lesnes Abbey Woods on 13 December 2026 in memory of Ray Marshall, with manual timing and a 90 minute cut off.
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.
Navigate an 11 mile circular trail between Maldon and Mundon using written instructions on a course that is 95 percent off road.
A charity off-road three mile run in Saltwood on 26 December 2026 that usually attracts over 1,000 entrants, with medals for all finishers and several entry options.