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.
May 2027
A two day, two person self supported navigation event at Newlands Corner with camping, maps and a points based route across the Surrey Hills.
Inflatable 5K in Guildford on 8 May 2027 offers lap-based inflatable obstacle distances from 2.5k to 15k, music zones, water stations and finisher medals.
A guided 30 km trail run through the Chiltern Hills with technique instruction, checkpoints, refreshments and a finisher's medal near Tring Station.
Two day obstacle race weekend in Henley on Thames featuring Sprint, Super, Beast and kids races across historic town and riverside terrain.
A 50-mile point-to-point ultramarathon on the North Downs Way from Farnham to Knockholt Pound with about 5,600 ft of ascent, six aid stations, medical support and a 13 hour cutoff.
A mid May running festival in Hackney featuring a 21.1 km half marathon on closed roads, a 10 km night run, community 5K and off road 5K, a schools challenge and a free two-day festival at Hackney Marshes.
A weekend of waymarked trail runs and walks at Mapledurham House near Reading, featuring ultras, a half marathon and supported marathon-length walks.
A single-lap 50 km multi terrain ultra in Maidenhead on May 22 2027, mainly off road along the Thames Path, Jubilee River and the Green Way. Four aid stations, chip timing, live tracking and on-course nutrition support.
A 5 km obstacle event at War Memorial Park on 23 May 2027 where participants climb, crawl and slide across mixed grass and path terrain; entrants must be 13 or older and a minimum fundraising target of £50 applies.
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.
Trail event from Richmond to Brighton offering multiple distances, GPS tracking, covered rest stops, medical support, camping and finishers items.
A 60 km point to point ultramarathon along the Ridgeway National Trail from Ivinghoe Beacon to Ridgeway View Campsite, fully marked with open tracking and four checkpoints.
June 2027
A 24 hour relay at Wasing Park, Reading where Solos, Pairs and Teams run an undulating 8 km trail lap with camping and an on-site event village.
A 5k obstacle course at Royal Windsor Racecourse with mud obstacles to climb, crawl and slide, mixed tarmac and grass surfaces, staggered wave starts and a minimum age of 13. Earlybird entry prices and a fundraising target apply.
A 5 km obstacle course at Prospect Park in Reading where participants climb, crawl and slide across grassy slopes and woodland. Waves run every 15 minutes and the event is open to people aged 13 and over.
Two trail distances around London on the Capital Ring with feed stations, chip timing and a planned finish at Old Deer Park, Richmond.