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

November 2026
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.
Seven hour time challenge on a signed riverside loop in Staines offering distances from 3 km to ultra, themed medals, goody bags and the book's author as guest.
A timed, lapped Cakeathon at Mowsbury Park on 22 November 2026 offering flexible starts, a flat 5.3 km lap, distances from 5 km to ultra, and a seven hour limit.
Berks, Bucks & Oxon Cross Country Championships at Broughton Castle on 22 November 2026, with junior and senior races, team scoring and chip timing.
Three evening trail time trials in the Chilterns on 23 September, 21 October and 25 November, each on a marked, chip timed course of about 8 km with a head torch required.
A community silent disco run at Rose Hill Community Centre on 28 November 2026 with a group warm up, headphones for music, glow items, post-run music, raffle and on-site refreshments.
A looped race series where entrants choose how many laps to run on the day, with aid stations, medals, medics and manual timing across several venues.
A community charity run in Campbell Park, Milton Keynes offering 1.5k, 5k, 10k and half marathon options with chip timing, medals, refreshments and a fancy dress element to support Movember and men's health.
A 7 hour Time Challenge along the River Thames with flexible distances, themed medals, goody bags and Krispy Kreme donuts at the finish.
Trail races at Mapledurham Estate in 2026 with 10K, 10 mile and half marathon courses across muddy paths, woods and estate roads and postrace refreshments.
Community 5 km fun run and children's Dasher Dash at The Forest Centre Marston Moretaine on 29 November 2026 raising funds for Mind BLMK.
Watlington XC 10k is a 10 km cross country fell run over the Ridgeway and Chiltern Hills for runners aged 16 and over, with pre-registration required and no entries on the day.
December 2026
A timed challenge along the River Thames in Staines offering distances from 5 km up to 50 km with a medal, bobble hat and on-course aid.
A charity trail event supporting the Hospice of St Francis with a guided 8 km run and a 4 km family walk, mince pie included and dogs welcome with canicross equipment.
An end of season trail championship at Wendover Woods featuring a 10 km route with 295 m of climb, chip timing and entry for qualified runners.
A Santa themed community run at Wembley Stadium on Wednesday 9 December 2026 with a charity toy drive, a £50 prize for most laps and refreshments available.
A festive time challenge along the River Thames in Staines where runners choose distances from 3 km up to 50 km. The event is signed, offers medals and pins, aid stations and goody bags.
Forest trail event at Salcey Forest on 13 December 2026 with 10 km, 5 km and a 1.2 km junior run, medals, prizes and fundraising for Shelter.
Join a festive Christmas run along the flat Jubilee River. Choose your own distance in this 6-hour timed event on a scenic towpath. All finishers receive a bespoke festive medal.
Trail runs at Wendover Woods in the Chilterns offering a family Santa Mile plus 5 and 10 mile races with chip timing, medals, and finishers refreshments.
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