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.
December 2026
A looped trail event in Crystal Palace Park where runners complete 2.65 km laps within a 7 hour time limit. Distances range from 5 km to ultra and all participants receive a finishers' medal.
January 2027
An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.
Running at Bewl Water on 10 January 2027 with 10k, 5k and a junior run on multi terrain routes beside the reservoir; maps and GPX files are provided.
A 10‑mile and 5‑mile trail challenge at Pippingford Park with 1568 ft of climbing, hard packed forest trails, wide views and bespoke medals.
February 2027
Trail races of 10 Mile, 5 Mile and a junior run take place in Bedgebury National Pinetum & Forest on 7 February 2027. The undulating multi terrain courses can be muddy after wet weather and include a bespoke medal and free photos.
A timed lap event in Crystal Palace Park on 21 February 2027 where runners complete 2.65 km laps to reach distances from 5 km to ultra, with a seven hour limit and a finishers' memento for all participants.
A single lap undulating 10k trail race at Hadleigh Country Park with steep hills, deep mud, technical terrain and mandatory trail shoes.
March 2027
May 2027
A four leg stage trail relay along the Roach Valley Way covering 23 miles in total. Teams of four navigate by maps and way markers while proceeds support Havens Hospices.
Muddy obstacle races at the Secret Nuclear Bunker Estate in Essex with 6 km (40+ obstacles) or 12 km (70+), featuring a 20 foot Deathslide and zip lines.
Off road 10 km, 5 km and family runs at Milton Creek Country Park on 9 May 2027 supporting The Oliver Fisher Special Care Baby Trust. Varied trail terrain, route maps and event medals are provided.
A multi distance trail event around Bewl Water reservoir near Lamberhurst, Kent. Races include 50km, marathon, half marathon and 10km on wooded trails and country lanes with start and finish at the Visitor Centre.
Inflatable 5K at Brands Hatch offers laps of 2.5 km with giant inflatable obstacles, multiple distance options, music zones, finisher medals and on course hydration.
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.
Point-to-point 50 km trail from Rochester to Tonbridge along the River Medway, predominantly flat with four aid stations, chip timing and an athletics track finish.
Point to point 30 km trail race along the River Medway from East Farleigh to Tonbridge with three checkpoints, chip timing and an athletics track finish.
Park-based 3k and 5k runs at Dunorlan Park with mixed grass and woodland terrain. The event is organised by Cancer Research UK and includes a fundraising pack and a finishers medal.
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.
A trail half marathon from Chiddingly, Sussex along the Wealdway and Vanguard Way with two checkpoints, chip timing, a five hour limit and a choice to donate instead of a medal.