Maidenhead
Trail Running Calendar near Maidenhead 2026-2027
Explore the top trail runs near Maidenhead for 2026-2027! We've gathered 227 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
March 2027
A guided trail half marathon around the Surrey Hills, about 13 miles from St Martha's Hill in Guildford, following parts of the North Downs Way and notable viewpoints. The run is social in format with a guided pace and evening options.
A 17.5 miles clockwise boundary trail race around Ashridge Estate, starting and finishing at Aldbury Recreation Ground, with water, a finisher gift and prizes.
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.
A two lap multi terrain 10 km trail race on Easter Monday around Mortimer Fairground and local woodlands, with a canicross option, chip timing, medal and free race photos. The undulating course is not suitable for pushchairs or wheelchairs.
April 2027
Trail run in Windsor on 4 April 2027 offering 10K and Half Marathon routes through Alexandra Gardens with Windsor Castle as a backdrop.
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.
Trail running at Froyle Village Hall with 10 km and 21 km options, waymarked routes, marshals, water stations, event photos, and proceeds supporting the village hall.
A guided 42.2 km trail run through the Chiltern Hills with qualified Run Leaders, checkpoints, mandatory trail shoes and a wooden finisher's medal.
A multi terrain run at Dummer Down Farm on 18 April 2027 offering 10 km, Canicross 10 km and a half marathon with a finisher medal and a Dell pint cup.
An untimed inflatable obstacle event in St Albans on a 2.5 km lap with distances from 2.5K to 15K, medals, music zones, and on-site facilities.
An alternative to the London Marathon at Walton on Thames featuring a UKA certified 3.28 mile lap. Options include full and half marathon or a seven hour timed event, with a 150 mm finish medal for participants.