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.
February 2027
A fully signed 50 km trail ultra on the North Downs Way and Norbury Park with about 2986 ft of ascent, four checkpoints and a finishers medal, based at Denbies Wine Estate.
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.
Group guided 10 km trail run across the boardwalk and heathland of Thursley National Nature Reserve with evening and night options, car parking and a post-run alcohol-free beer.
Saturn Running's Midweek Chasing Numbers in Staines is a seven hour time challenge along the River Thames with flexible lap distances and finisher medals.
March 2027
Guided 10 km trail run around Silent Pool near Guildford, following parts of the North Downs Way and Netley Heath forest. Sessions run at dusk or at night with headtorches in a led group and a recommended pace of about 10 min per mile.
A 7 hour Time Challenge along the River Thames where participants choose distances from 3 km up to ultra with medals, distance pins, goody bags and aid stations.
A Friday timed run at Xcel SPORTS HUB Stadium with flexible rock up and run starts, lap distances along the Thames and a charity medal for the Run for a Tenner entry.
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.
Multi terrain 10 km by the River Thames near Windsor & Eton Brewery with a finisher medal, a drink option and a commemorative pint cup.
Trail half marathon in the Chiltern Hills covering 13 miles with 300 m ascent, led groups, a midway refreshment point and a finisher’s medal.
A 24-hour endurance event at Alice Holt Forest where runners repeat a 6.7 km loop each hour, aiming to complete as many laps as possible.
A quirky running event in Dorking where pairs carry an adult over a 380 m out and back course with obstacles, a weigh in, helmet requirement and novelty prizes.
A hilly 13.1 miles out-and-back trail from Dorking to Leith Hill Tower with about 1,800 feet of ascent, water stations and marshals. Race HQ is The Priory School and entry includes a postrace cooked breakfast and a reusable medal.
Twelve consecutive days of timed riverside running in Walton on Thames with multiple distance options, collectible daily lantern medals, finishers shirts, and a Double-Down option to run two half marathons each day.