Trail Running calendar near Winchcombe 2025-2026

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 Sheinton Steeplchase is a 5.3 km cross-country race held near Sheinton Church by Cressage in the West Midlands. Featuring a total ascent of 100 meters, it offers a challenging yet accessible course that is not a traditional fell race bu..

Tackle the Bat Challenge at Beacon Hill Country Park: a six hour off road loop where you choose your pace and complete as many 3.3 mile laps as you can. Expect a steady climb to scenic high points and a fun, supportive atmosphere.

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.

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..

Join a friendly, inclusive weekend of trail running and festival fun at scenic Deene Park near Corby on May 9 and 10 2026. Pick from short loops, an evening 10k, a hilly half marathon or the full challenge, with medals for all finishers.

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..

Epona 100 is a bold 100 mile trail race from Abergavenny that links Offa's Dyke, the Cambrian Way and the Beacons Way across roughly 17,000 ft of ascent. Expect rugged trails, aid station support and a generous 50 hour time limit.

Join the Ridgeway 40 on May 9 2026 for a scenic 40 mile walk along the Ridgeway across chalk downland. Limited entries and checkpoint support make this a rewarding challenge for prepared walkers.

Apocalypse Ultramarathon in Church Stretton on 9 May 2026 offers 10 to 50 mile options across four scenic but brutal loops. With a 16 hour limit, rolling food at HQ and limited places this is a bold endurance challenge.

Explore Northamptonshire on the Shires and Spires Anti Clockwise Edition, offering 10K up to a 35 mile ultra across scenic roads and trails. Waymarked routes, checkpoints and GPS support make this a great test of stamina and navigation.

Take on the Greenway Challenge in Letchworth Garden City: a self guided 13 mile clockwise run starting and finishing at Standalone Farm. Enjoy marshalled crossings, a wooden medal, and cake at the finish while supporting Headway Herts.

Tackle the scenic and challenging North Downs Way 50, a 50 mile trail run from Farnham to Knockholt Pound on 16 May 2026. Expect rolling hills, great trail views, well stocked aid stations and a friendly Centurion Running race atmosphere.

On 16 May 2026 choose the OTT Trail Marathon or 10 Mile in the Brecon Beacons, tackling Pen Y Fan and rugged upland trails. Expect epic views, testing climbs and a friendly finishers vibe with a coaster and buff for everyone.

Take on the True Grit Trail Half Marathon on 16 May 2026 for a gritty 13.1 mile test across quarry sections, forestry trails and the scenic Bedford Park. With 50 places available this muddy, wild route rewards finishers with a bespoke medal..

Run the scenic Berkshire Downs at the Compton Downland Challenge on 16 May 2026, with 26.8 mile or 16 mile trail options along the ancient Ridgeway. Expect climbs, muddy paths, aid stations, chip timing and a hearty post race BBQ.

Tackle the Merrell Cannock Chase Challenge on 16 May 2026 at Tackeroo Campsite with 10 km, half or full marathon over scenic off road trails. Limited to 500 entries, enjoy rolling terrain, aid stations, free parking and a finisher medal.

The Shindig in the Shire showcases scenic routes past Ironbridge Gorge and the Iron Bridge, with some climbs to keep it lively. Pick 8, 16 or 26.2 mile courses and enjoy finisher bling, ales and pub food at The Unicorn Inn.

Join the Semington Slog on 16 May 2026 at St Georges School for 10k and 2k routes through the village and along the Kennet and Avon Canal towpath. Family friendly fun with marshalls, refreshments and a Slog Dog for every finisher.