High Wycombe
Trail Running Calendar near High Wycombe 2026-2027
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.
October 2026
A monthly five mile run in Wimbledon organised by Thames H&H running club, held on the second Sunday of each month with online entries and published results.
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 guided 10 miles through the Chilterns along canals, reservoirs and past Britain’s oldest post windmill, with trail instruction and a finisher’s medal included.
Off road cross country race of about 6 miles around Manor House Farm in Hardwick, with water crossings, limited to 300 runners and minimum age 17.
Trail runs of 10 km and 5 km around Blackpit Brewery on October 18 2026, using private multi terrain trails through woodlands and estate tracks. Entrants receive a medal, a pint cup and a free drink at the finish.
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, themed medals and distance pins, an aid table, goody bags including a vegan option, and on the day number collection.
Conquer 58 floors and over 1,500 steps at 22 Bishopsgate to support RNLI lifeboats while enjoying panoramic views of the London skyline.
Looped events where runners choose how many laps to run on the day, with maps, aid stations every lap and distances from 5K to 50K across several venues.
A social 8 km trail run on the North Downs from Greyfriars Vineyard, finishing with lunch, a glass of English sparkling wine and a guided wine tasting.
Single loop 50K trail race around the Chilterns from Berkhamsted with three aid stations, fully marked navigation and a 9 hour cutoff.
Halloween-themed Time Challenge in Staines along the River Thames with distances from 3 km up to 50 km and medals for finishers.
November 2026
Autumn trail races at Wendover Woods offering Marathon, Half Marathon, 10k and Junior Run on hilly, multi-terrain loops with on-site facilities and a six hour cut off.
Two days of marathon and half marathon races around Caldecotte Lake in Milton Keynes on 6 and 7 November 2026, with multi-lap clockwise courses, on-course water and toilets, enforced time limits, and bespoke finisher medals.
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.
A seven hour timed event in Staines upon Thames on 6 Nov 2026 offering distances from 5 km to ultra, a poppy finisher medal, and on-course aid with vegan options.