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Trail Running Calendar near Medstead 2026-2027

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Explore the top trail runs near Medstead for 2026-2027! We've gathered 140 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Timed fell run on Butser Hill in the South Downs, with junior and senior races and proceeds supporting The New Blendworth Centre.
A Henley basecamp trail event with looped options of 50 km, 25 km and 10 km, covered rest stops, GPS tracking, medical support, camping and finish-line hospitality.
Trail races at Amport Cricket Club with 5k, 10k, 10 mile and canicross on marked multi-terrain routes, cupless stations, first aid and finish-line refreshments.
A community road and trail event at Nettlestone Primary School with 5 miles, 5 km and a children's fun run on circular seaside routes with finish medals.
Enjoy a coastal run along the Hayling Billy Line with a 6 hour time limit to complete your chosen distance at your own pace.
A mixed terrain 10 km race across the grounds of Highclere Castle on 27 September 2026 supporting Thames Valley Air Ambulance and Newbury AC.
October 2026
A 7 hour Time Challenge on a signed riverside loop in Staines offering flexible distances from 3 km up to 50 km, with medals, distance pins, aid stations and goody bags.
Guided 30-mile trail run on the North Downs Way from St Martha's Hill to Box Hill with coach support, group pacing, and nearby transport; entry £55.
Trail running from Queen Elizabeth Country Park across the South Downs with five distances from 6 km to 51 km, marked courses and on-course fuel outposts.
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
Forest of Bere timed event with flexible start format, a 3.28 mile lap and options from 5 km to ultra. Aid station offers sweet and savoury food including signature potatoes and vegan choices; 20% of proceeds go to Forestry England.
Scenic half marathon and 10KM at RAF Greenham Common, family friendly and supporting New Life Special Care Babies.
Run Beaulieu on 4 October 2026 offers off-road 10k, 5k and 3k runs at Beaulieu Estate with proceeds supporting the Countryside Education Trust.
Trail running in Hurtwood Forest near Guildford with 15 km and 21 km routes, on-site facilities, water stations and medals for all.
Trail races at Cowdray Estate on 10 October 2026 offering 10 mile, 10 km, 5 km and a new 3 km kids run alongside Cowdray Farm Shop Apple Day.
Four seasonal trail races at Cowdray Estate near Midhurst offering 3km kids races, 5km, 10km, 10 mile and CaniRun categories with series prizes.
Trail and fun runs near Old Basing on 11 October 2026 with chip-timed 10K and 6K races plus a 2K family fun run supporting local schools.
Flat mixed trail races along the Basingstoke Canal and through Wellesley Woodlands with 10 km, 5 km and a 2 km fun run, chip timing and a collectable medal.
Wacky Run Six in Fareham on 11 October is a themed run with an Army Surplus Special atmosphere, a six hour personal-distance format, themed medals and limited entries.
A 100 mile trail race from Goring & Streatley using Thames Path and Ridgeway in four 25 mile out and back spurs, with 16 aid stations and a 28 hour cut off.
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