Trail Running calendar near Winchester 2025-2026

Saturn’s Midweek Chasing Numbers 7-Hour Time Challenge is held at Wraysbury Skiff & Punting Club on the River Thames. The event is designed to be affordable and flexible, inviting all abilities to run or walk within a 7-hour window. Partici..

Enjoy a three day running festival over the May Bank Holiday across three Mid Sussex towns. Run single town races or combine stages into the Mid Sussex Marathon, with undulating multi terrain routes, medals, family fun and fancy dress.

Join Run Silchester on 2 May 2026 for 2.5, 5 and 7 mile trail runs around the Roman wall, ancient woodland and a 12th century church. Family friendly festival atmosphere with stalls, music and proceeds supporting local community causes.

Take on the iconic Thames Path 100 from Richmond to Oxford, 100 miles of scenic riverside trails and historic towns. Enjoy waymarked routes, plenty of aid stations and a supportive ultra atmosphere for a true point to point challenge.

Join a guided 30 mile trail run along the North Downs Way and Greensand Way led by an experienced ultra runner and coach in a supportive group run. Enjoy sweeping hilltop views, shoe demos and a possible alcohol free beer at the finish.

Experience the Isle of Wight Ultra Challenge from Chale, tracing dramatic coastal cliffs past the Needles, Cowes and Ventnor. Multiple distances, strong support and camping options welcome runners and walkers seeking a scenic big day or two..

Run a scenic woodland course at Culden Faw Estate on 3 May 2026 with solo, pair and team relays plus timed 5K, 10K and the Henley Downhill Time Trial. Expect gentle undulations, a climb before 3 km and a long downhill finish with chip timin..

Hit the Cotswolds trails with Tempo Trail Races on Sunday 3 May 2026, featuring distances from 10K up to a 100K ultra. Pick your challenge or try the new 50K option for a weekend of scenic, adventurous running.

The Bluebell Bash is a trail running event in Manswood, Wimborne, UK, organized by Tri-Counties Trail Running. It offers three distances—half marathon (13.1 miles), 10K, and 5K—with full accessibility for canicross. Runners traverse scenic..

Join a guided Box Hill Vertical KM group run near Dorking for a tough 12.5 mile route with about 1000 m of climb through woods, heath and open fields. Enjoy expert guidance, technical terrain and a social finish.

Take on the Three Forts Challenge across the South Downs with rolling hills and coastal views. Choose marathon, half marathon or 5 mile trail and even bring your dog, with net proceeds supporting local Sussex charities.

BigWayRound Winchester is a scenic trail run from 14 miles to a 50K ultramarathon across the South Downs and along the River Itchen, with chip timing and self seeded waves. Choose a finisher medal or plant a tree to celebrate your finish.

Enjoy spring trails at Harewood Forest in Hampshire with Muddy Runners, choosing from 5 km or 10 km routes across undulating woodland tracks. A friendly, scenic race perfect for trail newcomers and regulars alike.

The Collingbourne Races, held at Crawlboys Farm in Ludgershall, offer a scenic off-road running experience through the beautiful Collingbourne woods. Featuring a half marathon and a 10km race, the course includes bridle paths, woodland trac..

Take on the Westcountry Ultra Flat, a 50 mile point to point ultramarathon on 9 May 2026 from Taunton to Minehead. Enjoy a pancake flat first half followed by scenic coastal climbs, rocky beaches and unforgettable views to the finish.

Run to the Sea Brighton is a point to point 50 km ultramarathon from Christs Hospital to Hove Lawns, taking in trails, rolling downs and a seaside finish. Fully signed route, aid stations and pro medical support make for a scenic coast boun..

Take on the Westcountry Ultra 100 mile point to point across Somerset coastline and countryside, with coastal paths, limestone cliffs and a dark skies reserve. With a 32 hour cut off and 13 aid stations, this scenic but demanding ultramarat..

The Goring Gap Trails event, held in Mapledurham near Reading, offers a variety of running and walking challenges, including a 50-mile ultra, a 52K ultra, and a half marathon, alongside walking options of half marathon, full marathon, and a..

Take on the Chiltern Hills 100K, a scenic but testing ultra with over 1800m of climb through Ridgeway and Ashridge landscapes. Limited to 250, this TRA licensed UTMB index race combines marked trails and excellent support.

Test your limits at Brighton Backyard Ultra in Stanmer Park where runners tackle a 6.7 km loop each hour until a solo lap crowns the winner. A friendly but fierce endurance event in beautiful parkland with basic on site facilities.