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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 149 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

A 7 hour time challenge at Northampton Active offering flexible distances from 3 km to ultra with medals, goody bags, aid stations and distance pins.
Saturn Running's Midweek Chasing Numbers in Staines is a seven hour time challenge along the River Thames with flexible lap distances and finisher medals.
March 2027
A 7 hour Time Challenge along the River Thames where participants choose distances from 3 km up to ultra with medals, distance pins, goody bags and aid stations.
Multi terrain 10 km by the River Thames near Windsor & Eton Brewery with a finisher medal, a drink option and a commemorative pint cup.
Trail half marathon in the Chiltern Hills covering 13 miles with 300 m ascent, led groups, a midway refreshment point and a finisher’s medal.
Trail races from Harrold-Odell Country Park offering 25 km and 50 km routes through Bedfordshire on 13 March 2027.
An all-female trail event at Culden Faw Estate near Henley on Thames offering 3 km, 6.5 km and 13 km routes with timed results and on-site refreshments.
Experience a 50km trail ultra through the Chiltern Hills with two scenic loops starting and finishing at the historic Stonor Park.
A 7 hour time challenge around the Northampton Washlands offering distances from 3km to ultra, with medals, pins, goody bags and aid stations on maintained paths.
A 17.5 miles clockwise boundary trail race around Ashridge Estate, starting and finishing at Aldbury Recreation Ground, with water, a finisher gift and prizes.
April 2027
Trail run in Windsor on 4 April 2027 offering 10K and Half Marathon routes through Alexandra Gardens with Windsor Castle as a backdrop.
Scenic mixed terrain races along the Thames at Remenham Farm in Henley on Thames. Options include a Half Marathon, a 10K and a Junior Race with marked trails, marshals, chip timing and post race goodies.
Races on the Thames Path at Wraysbury Skiff & Punting Club in Runnymede offering Marathon, Half Marathon and 10 km courses with marked turnaround points and stocked checkpoints.
A 50K trail ultra along the Ridgeway in the Chiltern Hills, starting at Berkhamsted Castle and finishing in Wendover, with three checkpoints and a 9 hour limit.
Windsor 50 offers supported looped trail routes of 50 km, 25 km and 10 km from Windsor Racecourse through the Great Park, Thames Path and Runnymede.
A guided 42.2 km trail run through the Chiltern Hills with qualified Run Leaders, checkpoints, mandatory trail shoes and a wooden finisher's medal.
Multi-terrain 5 km and 10 km races at Ibstone with routes through Wormsley Estate plus a 1 km or 2 km Run in Colour for ages 4 to 11.
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