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Trail Running Calendar near Aylesbury 2026-2027

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Explore the top trail runs near Aylesbury for 2026-2027! We've gathered 180 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2027
Pilgrim's Reckoning is an 81 mile circular ultra on the Bunyan Trail in Bedfordshire with a waymarked route, seven aid stations, medical support and a 40 mile option.
A 10 km trail run around Sandridge, St Albans, starting at Woodcock Hill on 12/09/2027 with entry listed at GBP 23.
A single 50 mile loop through the Chiltern Hills with 5600 ft of climb, five aid stations, a fully marked route and race medical support within a 13 hour cut off.
One-day trail event around Tring with routes between 10 and 50 km to raise funds for Humanity Direct, featuring marked routes, checkpoints and on-course medical support.
Looped trail options from 10K to approx 100 km around the Chilterns with covered rest stops, GPS tracking and on-site camping at Henley Basecamp.
A technical off road trail race in Marlow on 26 September 2027 through Chiltern woodlands and chalk ridges, with sustainable race practices and chip timing.
October 2027
A fully marked 100K trail ultra around the Chiltern Hills with six checkpoints, 1800 m ascent, GPS tracking and an event base in Chesham.
Multi-terrain 5 km and 10 km races at Blackpit Brewery near Silverstone and Stowe on 3 October 2027; finishers receive a medal, a free pint and a Blackpit pint cup.
Backyard Ultra at Turvey House on 9 October 2027 challenges runners to repeat a 4.167 mile (6.7 km) loop every hour with solo, paired and 8 hour options.
Trail race in the Chiltern Hills near Marlow and Henley on Thames with 5 km and 10 km routes, community fundraising, medals and on site refreshments.
A 100 mile trail race from Goring and Streatley run as four 25 mile out and back legs on the Thames Path and Ridgeway, with 16 aid stations and a 28 hour cut off.
A 10 km road race in Wolverton, Milton Keynes on 28 October 2027 with tiered entry fees and registration opening 29 October 2026.
A fully marked single loop 50K trail from Berkhamsted through the Chilterns with three aid stations, required navigation and a nine hour time limit.
November 2027
Enigma Fireworks in Milton Keynes on 5 and 6 November 2027 stages marathon and half marathon races around Caldecotte Lake with clockwise laps and time limits.
Point to point Half Marathon along the Grand Union Canal from Cowley to Cassiobury Park, Watford, on towpaths, trails and woodland. Entry from £35.
A Remembrance Day Time Challenge along the River Thames offering distances from 3 km to ultra with medals, distance pins and on course aid.
Trail races through Alexandra Gardens with 10K and half marathon options, chip timing, free photos and support for Brain Research UK.
December 2027
Riverside trail run from Windsor along the Thames with signed courses of 21.8K or 15.7K, chip timing and a finisher medal.
A winter cross country 10 km at Renegade Brewery in Yattendon on 24 December 2027 with a medal and a drink for every finisher.
A lakeside Christmas marathon and half marathon at Caldecotte Lake with looped, mostly gravel paths, finisher medals, water provision, and on course support.
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