Medstead
Trail Running Calendar near Medstead 2026-2027
Explore the top trail runs near Medstead for 2026-2027! We've gathered 146 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A repeated loop Backyard Ultra around Chilton Manor Farm featuring private trails, varied terrain and a scenic climb to Bugmore Hill Trig Point, with base camp facilities and an aid station.
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 3 hour timed event on 25 October in Portsmouth where runners choose 5K, 10K or a Half Marathon and bring non-perishable food donations for a local food bank.
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.
November 2026
Coastal 15.3k, 10k and 5k runs along West Wittering Beach with sea views, chip timing, on course water and a finisher medal.
Event Seven of the Wacky Races series is a seafront running event on 1 November 2026 at The Shack, Lee-on-the-Solent with 5K, distance-building options and a 6-hour challenge.
A 5km run at Osborne House on the Isle of Wight featuring woodland, parkland and coastal sections with free entry for up to three spectators per runner.
Trail run from Goodwood Racecourse into the South Downs with three distances, varied trails, scenic views and finisher medal and refreshments.
A torchlit trail run from Winchester Athletics Track with 12 km and 22 km options across the South Downs Way and local trails. The course is fully marked; headtorches and at least 500 ml of fluid are required.
Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.