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Trail Running Calendar near Chesham 2026-2027

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Explore the top trail runs near Chesham for 2026-2027! We've gathered 201 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

Riverside out and back races from Small Profit Dock Gardens along the Thames Path offering 10 km, half marathon and marathon courses with stocked checkpoints and medical support.
A largely flat 10 km multi-terrain run from Windsor & Eton Brewery with chip timing, a medal, a pint cup and a free drink at the finish.
Trail half marathon in the Chiltern Hills covering about 13 miles with grouped pacing, run leaders, a refreshment point, on site parking and a finisher medal.
A seven hour Time Challenge along the River Thames in Staines offering multiple distances, themed finisher medals, aid stations and goody bag options.
Women only trail runs at Culden Faw Estate, Henley on Thames, on 14 March 2027 with 3 km, 6.5 km and 13 km options, chip timing and finisher medals.
Multi day running series in Walton on Thames offering Ten in Ten and Twelve in Twelve formats with distances from 5 km to ultra, certified flat riverside laps and finishers medals and shirts.
A 7 hour time challenge along the River Thames with flexible lap distances from 3 km to 50 km, medals, distance pins, aid stations and goody bags.
Experience a 50km trail ultra through the Chiltern Hills with two scenic loops starting and finishing at the historic Stonor Park.
London Lea Valley Ultra is an ultramarathon event in London on 20 March 2027 organised by Camino Ultra.
A trail race of approximately 17.5 miles around the Ashridge Estate boundary on well marked paths, with water stations, finisher gifts and prizes for top male and female runners.
A 25 kilometre canal run in Welwyn Garden City on 20 March 2027, organised by Camino Ultra, with mostly flat tow path terrain, well stocked aid stations and supportive volunteers.
Trail races through Danesfield woodland near Marlow: 10K, 6.5K and a 1K junior race with on course water and chip timing.
Seven consecutive days of timed running on certified out and back routes along the River Thames in Walton on Thames. Distances from 5 km to ultra are available and finishers earn daily mementos plus a seven day lantern medal set.
Seven consecutive days of timed running along the River Thames with flexible distances from 3 km up to 50 km, lap-based half, full and ultra options, daily medals and pins, aid stations and goody bags.
April 2027
Time challenge on signed loops beside the River Thames with distances from 3 km to 50 km, medals and pins, goody bags including vegan options, and on-course aid.
Trail event in Windsor on 4 April 2027 with 10K and half marathon options, a flat course through Alexandra Gardens and proceeds supporting Brain Research UK.
A timed Friday run on a flat 5.3 km Thames towpath lap with flexible starts; the £10 charity entry supports Rays of Sunshine and all finishers receive a medal.
Scenic mixed terrain races along the Thames at Remenham Farm in Henley on Thames. Options include a Half Marathon, a 10K and a Junior Race with marked trails, marshals, chip timing and post race goodies.
Races on the Thames Path at Wraysbury Skiff & Punting Club in Runnymede offering Marathon, Half Marathon and 10 km courses with marked turnaround points and stocked checkpoints.
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