Maidenhead
Trail Running Calendar near Maidenhead 2026-2027
Explore the top trail runs near Maidenhead for 2026-2027! We've gathered 228 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A trail half marathon from Creasey Park across the Dunstable Downs, run mainly on footpaths and bridleways. The self navigated course includes checkpoints and guide runners, a GPX file, on course drink stations and event facilities.
30 August 2026 in Alexandra Gardens Windsor offers 10K and half marathon routes with views of Windsor Castle. The event includes chip timing, free race photos and an event village.
Day nine of the Duck n Run Totally Quackers series on 30 August 2026 in Walton on Thames features timed laps on a flat riverside out and back course, with distances from a single 3.28 mile lap up to an ultra within seven hours.
September 2026
A mixed terrain trail along the Thames at Remenham Farm in Henley on Thames offering a half marathon, 10K and a junior race, with chip timed results, a themed medal and free race photos.
Choose a half marathon or full marathon along a flat, scenic riverside towpath from Walton on Thames to Hampton Court and back, run in laps for easy pacing. Limited places and medals for all finishers plus a giveaway for every entrant.
A 12-hour looped run at Bloor Homes Southern Regional Office in Newbury where participants complete 3.5 km loops to earn a bespoke medal, with prizes for most loops. The event supports New Life Special Care Babies, is limited to 100 entrants and is 1..
An ultra endurance event in Heartwood Forest where participants cover four mile loops within a 12 hour window, solo or in relays up to eight people. Winners are decided by distance and all finishers receive a medal.
Half marathon and 10k at Wimbledon Common on 6 September 2026, with marked trails, marshals and a 3.5 hour cutoff. An event village offers food, drink and finish line goodies and the event supports the Beder charity.
A scenic 10K through the private grounds of Loseley Park in Surrey on 6 September 2026, with timed results, finisher medals and official photography.
Community led 10 km trail at Dummer Down Farm with chip timing, post run food and brewery drinks, a race village and a donation to Mind.
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 timed, lap-based Friday run along the Thames with flexible rock up and run starts; the £10 affiliated entry is donated to Rays of Sunshine and participants receive a double-sided charity medal.
A multi-distance walk, jog and run along the River Thames from Putney Bridge to Henley in September 2026 and 2027. Distances span 10 km to 100 km with rest stops, catering, medical support and GPS tracking via an event app.
Trail running in the Surrey Hills with 10k, 21k and 42k routes on chip timed, well marked courses, aid stations and finisher medals. Starts and finishes at Shere Recreation Ground with free parking and an event village.
A trail running event on 13th September 2026 in Seale, based at Myrtle’s Courtyard, with marathon and half marathon routes along the Pilgrims Way and North Downs Way that raise funds for local charities.
A wine-themed running event at Denbies Wine Estate near Dorking offering a half marathon and 10 km through vineyards with wine stops, food and live entertainment.
A 10 km trail race in Sandridge, St Albans on 13 September 2026, starting and finishing at Sandridge Primary School playing field. Organizers publish route information and FAQs, and the event is supported by Sandridge Parish Council.
An annual off-road event on Ashtead Common offering 10 km and 2 km races that raise funds for local charities while promoting low-impact travel.
Timed laps on a 5.3 km riverside course along the Thames allow runners to build distances from 5 km up to ultras. First 50 entries receive a black and yellow plushie and a Feisty mini me medal; a no medal option is available.