Maidstone
Trail Running Calendar near Maidstone 2026-2027
Explore the top trail runs near Maidstone for 2026-2027! We've gathered 63 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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 along the River Medway from Rochester to Tonbridge with four aid stations, live timing and an athletics track finish.
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.
Community 3k and 5k runs at Dunorlan Park on mainly grass and woodland terrain with some inclines and limited general parking.
Trail half marathon in Chiddingly, Sussex on 6 June 2027 with chip timing, two checkpoints, a 5-hour limit and a 400 runner entry cap.
Race for Life Basildon on 19 June 2027 at Gloucester Park offers 3k and 5k courses around park lakes with accessible facilities and a minimum fundraising target.
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.
Mud and water obstacle run at Hole Park Estate on Sat 19 Jun 2027 with 5k, 10k and 30k options and a 4.7 rating from 164 reviews.
A 24 hours endurance event at Cherry Orchard Country Park where solo runners or teams cover as many 8 km laps as possible to raise funds for homelessness in Essex.
Annual not for profit run organised by Istead & Ifield Harriers from Cyclopark through the Kent countryside with proceeds supporting local charities.
July 2027
A 24-hour multi-terrain relay near London offering solo or team entries (2 to 8 runners) on repeated 5.75 mile laps, with free camping and on-site facilities.
A multi-format running festival at Blackland Farm on 24–25 July 2027 offering 24 hour and 12 hour solos, team relays, P24/P12 challenges, camping options, and finisher medals.
August 2027
A bi-annual trail and road race series around Bewl Water in Kent offering 10 km, half marathon, marathon and 50 km ultra with lakeside views.
London Backyard Ultra at Frylands Wood Scout Outdoor Centre uses the Backyard Ultra format: run a four mile loop each hour until only one runner remains.
Experience a scenic 10k trail run through Shoreham Woods in Kent featuring chip timing and a dedicated Canicross category for runners with dogs.
September 2027
A bi-annual trail and country-lane race around Bewl Water in Kent offering 10 km, half, marathon and 50 km ultra courses with lake views.
A weekend of obstacle races at Pippingford Park on 25 and 26 September 2027 featuring Sprint, Super, Beast, Ultra, Trifecta racing and kids races.