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Trail Running Calendar near High Wycombe 2026-2027

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Explore the top trail runs near High Wycombe for 2026-2027! We've gathered 221 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Experience a scenic trail run through the Bedfordshire countryside with a choice of a half marathon or metric half marathon along the Grand Union Canal and woodland paths.
Three trail distances through Stonor Park and the Chilterns with marked courses, fuel outposts, on site facilities and notable gradients.
A fundraising running and walking challenge on 7 November 2026 offering 76 km from Aldershot or 36 km from Petersfield, finishing in the Historic Dockyard Portsmouth.
A trail event in Windsor on 8 November 2026 offering a 10K and a half marathon on flat off road trails from Alexandra Gardens. The event features chip timing, race photos, post race goodies and an event village.
A licensed 7 hour Time Challenge in Staines along the River Thames with multiple distances from 3 km to 50 km, commemorative medals and distance pins.
Remembrance Run in Surrey along the River Thames: a 7 hour time challenge with distances from 3 km to 50 km, medals, aid stations, and a two minute silence.
A riverside marathon and half marathon on 8 November 2026 featuring a two minute silence pause, flat towpath laps, limited places and medals for all participants.
Join a community of runners at Richmond Park for a series of timed races supporting Movember. Enjoy a hilly tarmac course with distances ranging from a kids mini run to a half marathon in a supportive atmosphere.
A point to point 13.1 mile race along the Grand Union Canal from Cowley to Cassiobury Park with chip timing, four water stations and an optional coach transfer from the finish.
Second Sunday 5 on 8 November 2026 at Richardson Evans Memorial Fields in Wimbledon Common is an informal two lap event organised by Thames Hare & Hounds.
A three day, 84 miles ultra along the Ridgeway from Buckinghamshire to Wiltshire with overnight stops, accommodation and food options.
A flexible Friday running event on a flat 5.3 km out and back course along the Thames offering distances from 5 km to ultra, timed over a seven hour limit with bespoke finishers medals.
A 50 mile trail race in Wendover Woods made of five 10 mile loops with 10,000 feet of climb, nine aid stations, medical support and a 15 hour cut off.
A multi-terrain 5K and 10K race in the Chiltern Hills on 15 November 2026, organised by the Radnage Primary School PTA, with water stations, first aid, a village hall cafe and proceeds supporting the school.
A 7-hour time challenge along the River Thames with distances from 3 km to 50 km, themed medals, aid stations and parking in Staines.
Walking and running event from Barton-le-Clay Village Hall with 12, 18 and 26 mile routes through undulating countryside and checkpoints on each route.
Timed multi-lap run on a flat Thames towpath in Walton on Thames with distances from 5 km to ultra, a seven hour limit, flexible one hour start window and finishers medal options.
A fully marked 50 km trail race from Putteridge Bury across the North Chilterns with three aid stations and an 8 hour 45 minute time limit.
Riverside trail run from Alexandra Gardens in Windsor with two distance options, chip timing, on-course support and a finisher medal.
Half day 6 miles 10 km trail run in the Chiltern Hills with a private Tring Brewery tour, tasting and a bottle or a pint included.
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