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

October 2026
Timed trail event in the Forest of Bere using a 3.28 mile out and back lap with distances from 5 km to ultra. Aid station offers sweet and savoury food including potatoes and vegan options; 20% of proceeds support Forestry England.
Half marathon and 10 km races at RAF Greenham Common in Thatcham, Berkshire. The traffic free, flat course has water stations, free parking and a children's race paid on the day for £5; proceeds support 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 events at Cowdray Estate offering 3 km to 10 mile options, CaniRun and kids races with series scoring, prizes, linking medals and free photos.
Community-supported trail runs at Old Basing offering 10K and 6K chip timed races plus a 2K fun run to raise funds for 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.
Biweekly free Sunday morning trail runs from Surrey Trek and Run with varied routes and distances, limited to 10 places per leader.
A 100 mile trail race from Goring and Streatley using the Thames Path and Ridgeway in four 25 mile out and back spurs, with 16 aid stations and a 28 hour cutoff.
Trail and multi terrain races at Dummer Down Farm on October 17 include a 10 km, a Canicross 10 km and a two lap half marathon with finishers' pint and camping option.
Trail races from Fernhurst Recreation Ground around Blackdown, featuring a 10 km route to the Temple of the Winds and shorter junior and adult options.
Social 8 km trail run with North Downs views, finishing at Greyfriars Vineyard for lunch, a glass of English sparkling wine and a guided tasting.
A relaxed three hour timed running event in Portsmouth on 25 October 2026 offering 5K, 10K and half marathon options while collecting food for a local food bank.
Biweekly free Sunday morning trail runs from Surrey Trek and Run with varied routes and distances, limited to 10 places per leader.
Night gravel runs in Alice Holt Forest offering 5 km, 10 km or 15 km on marked laps with one outpost per lap and parking on site.
Evening Halloween run at Hogmoor with kids and adult looped races, muddy sandy terrain, canicross, fancy dress and a medal for every finisher.
A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.
A Halloween themed backyard ultra at Meoncross School on 31 October to 1 November 2026 where runners repeat 6.7 km out and back laps until a single runner remains.
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