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Trail Running Calendar near Bembridge 2026-2027

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Explore the top trail runs near Bembridge for 2026-2027! We've gathered 74 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

January 2027
Timed out-and-back event on the Itchen Way in Winchester with multi-lap options, a themed atmosphere and an aid station with vegan choices.
Night time runs at Cowdray Park with 3 km kids, 5 km and 10 km options including dog friendly races; head torches required.
A four-race seasonal trail series at Cowdray Estate offering 3km kids, 5km, 10km and 10 mile courses, series prizes, linking medals and CaniRun options.
Trail run at Queen Elizabeth Country Park in the South Downs offering three off road distances, chip timing, on course refreshments and a finisher medal.
Timed out and back event on the Itchen Way in Winchester with 2.62 mile laps, flexible starts, an aid station with hot potatoes and medals for all participants.
February 2027
Single-loop trail races of 50 miles, 50K and 20 miles around Ditcham Park School in Hampshire, following parts of the Staunton and Monarchs Ways and the South Downs Way.
Two coastal half marathons in Portsmouth and Langstone Harbour over a Valentine weekend with an optional ferry crossing and a bonus medal for completing both.
Trail event at Queen Elizabeth Country Park on 21 February 2027 offering 16 mile, marathon and 50 km single-lap routes with aid stations and kit requirements.
A 30 mile non-competitive group trail run from Harting Down along parts of the South Downs Way, passing Beacon Hill, Cocking Down and Kingley Vale. Led by an experienced guide and recommended for those who have run at least 22 miles in training.
Coastal trail run around the Chidham Peninsula with harbour views, a low-tide foreshore crossing and options of 21.3 km or 16.1 km routes.
5k and 10k routes through Pondhead Inclosure raising funds for a new Lyndhurst FC clubhouse, with chip timing and Race HQ at the Crown Stirrup Pub.
Isle of Wight cross-country at Smallbrook Stadium with a 10 km championship race and a 6.5 km U18 course, marked trails, road crossings and onsite facilities.
March 2027
Coastal out-and-back at Milford on Sea with distances from 5K to ultra, 5.3 km laps, an aid station, medal and local facilities.
Wacky Run Eleven on 7 March 2027 at Meon Valley Trail offers timed six hour trail options from 5K to ultra, Mean Machine medals for finishers and 100 places only.
Point to point trail races on the South Downs Way offering a 50 mile ultra, a 50 km ultra and a marathon with marked routes, aid stations, coach transfers and an option to plant a tree instead of taking a medal.
Trail runs at Stansted Park near Rowlands Castle with three distances, woodland and South Downs views, chip timing, on-course support and a metal finisher medal.
Trail races of 5 km, 16 km and 24 km around Winchester in the South Downs with marked, timed courses and outposts for the longer routes.
A time-based trail challenge at Robin Hill where solo runners or relay teams complete as many 5 km laps as possible within 6 or 12 hours.
April 2027
A single loop 50 km trail ultra around the South Downs from Arundel with 3,200 ft elevation, four aid stations, full waymarking and 2 ITRA points.
Trail races at Cowdray Estate include 3 km kids, 5 km, 10 km and 10 mile options plus dog friendly canicross and a scored 10 km series.
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