Isle of Wight
Trail Running Calendar near Isle of Wight 2026-2027
Explore the top trail runs near Isle of Wight for 2026-2027! We've gathered 72 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
April 2027
A blindfolded navigation challenge in Winchester where participants are dropped at unknown locations and must find their way back on foot. Options include 6 miles for visitors and 10 or 15 miles; no maps or GPS and a sealed emergency bag is used.
May 2027
Coastal trek and trail event on the Isle of Wight with routes from 10 mile to 106 km, regular support stations, camping, transfers and GPS tracking.
A mud obstacle 5k at Southsea Common with climbs, crawls and slides on a mainly flat route. Waves start every 15 minutes, participants must be 13 or older, and the event supports fundraising for Cancer Research UK.
June 2027
BigSea on the Isle of Purbeck starts and finishes on Knoll Beach and offers Half Marathon, 18 Mile, Marathon and 54k routes across the Purbeck Hills and coastal landmarks. Aid stations provide snacks, water and vegan options and PH 1000 electrolyte d..
A 100 mile nonstop race along the South Downs Way on 12 June 2027, with 12 aid stations, a 30 hour cut off and mandatory kit checks.
A 50 km nonstop trail race across the South Downs National Park with 1150 m ascent, four aid stations, full medical cover and a nine hour cut off.
A muddy 5k obstacle course around The Common in Southampton where participants climb, crawl and slide through obstacles while raising funds for cancer research. Waves run every 15 minutes and participants must be 13 or older.
July 2027
Trail running event near Petersfield, Hampshire, offering 100k, 75k, 50k, 20k and 10k routes with camping, coach transport and on-site food.
A family friendly inflatable obstacle run in Southampton offering 2.5k, 5k, 10k and 15k laps with music zones, water stations and a finisher medal for every participant.
September 2027
A guided, hilly 30 mile trail run along the Jurassic Coast and Isle of Purbeck with coastal landmarks, group pacing and on-route guidance from an experienced ultra runner. Entry includes pre-run information and a possible alcohol free beer at the fin..