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.
October 2026
A lap based Friday timed run on the Thames towpath offering distances from a single 3.28 mile lap up to ultra distances, with the ten pound charity entry supporting Rays of Sunshine and a special double sided medal.
Trail and fun runs near Old Basing on 11 October 2026 with chip-timed 10K and 6K races plus a 2K family fun run supporting local schools.
Community organised 5k in Aldershot on 11 October 2026 with a flat course on the Polo Fields and Basingstoke Canal towpath, chip timing and finisher medals.
A scenic approximate 15 km trail race in Tring on 11 October 2026, routed through Ashridge Estate, the Ridgeway and Pitstone Hill with water stations and finish facilities.
A lap-based out and back run along the Thames in Walton on Thames offering distances from a single 5.3 km lap up to ultra distances with a seven hour limit.
A lap based Friday timed run on a flat 5.3 km out and back course along the river Thames, with distances from 5 km up to ultra. Both attended and virtual entrants receive a finisher medal.
A 100 mile trail race from Goring & Streatley using Thames Path and Ridgeway, with 16 aid stations, a 28 hour cut-off and strict qualification and kit rules.
A guided 10 mile trail through Chilterns waterways and reservoirs, passing Britain’s oldest post windmill, with trail instruction and a 2026 finisher’s medal.
An off road cross country race of about 6 miles across Manor House Farm in Hardwick village with varied terrain and water crossings. Entries are limited to 300 runners and a minimum age of 17 applies.
A point-to-point 47-mile ultra along the Thames Path from Iffley to Henley-on-Thames with five aid stations, mandatory kit requirements, and live GPS tracking.
Looped races at Chalfont Park and Chalfont St Peter let runners choose distances from a 7K loop to multi lap ultras. Aid station, clear course marking, crew support and medical cover are provided.
A fully marked single loop 50K trail race around the Chilterns starting and finishing in Berkhamsted, with three aid stations, mandatory kit and a nine hour cutoff.
November 2026
Trail races in Wendover Woods on hilly, multi terrain forest loops with marathon, half marathon, 10 km and a junior run plus on site amenities and parking.
Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.