Trail Running calendar near Chepstow 2025-2026

We have found 273 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

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 bluebell forests with gentle hills and expansive views.The e..

BigWayRound - Winchester is an award-winning, Gold-rated trail running event held at Winchester Rugby Club. The event offers four distances: 14 miles, 19 miles, a marathon, and a 50K ultramarathon, catering to both new and experienced trail runners. The course features stunning views and traverses i..

The Harewood Forest Trail Race is staged in Harewood Forest in the heart of the Test Valley, near Andover, Hampshire. Runners can choose between 5k and 10k trail routes on undulating forest tracks, offering a challenging yet scenic course. Described as a spring race set in a beautiful woodland setti..

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 but still highly regarded for its competitive and enjoyable na..

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 6-mile walk featuring a river boat crossing. The event is l..

UTMB Index

Westcountry Ultra Flat 50 is a point-to-point 50-mile ultramarathon organized by Albion Running. The event starts in Taunton and finishes at West Somerset College in Minehead. The route has a flat first half and a more undulating second half, with roughly 2,100 feet of elevation change, and is ideal..

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 tracks, and single-track trails, making it suitable for runners..

Westcountry Ultra Hilly 50 is a 50-mile trail ultra run by Albion Running, starting and finishing at West Somerset College in Minehead, Somerset. The route climbs about 7,337 ft, taking in North Hill and Bossington Hill, Culbone with the UK’s smallest parish church, Porlock Weir, and Dunkery Beacon,..

Westcountry Ultra 100 Miler is Albion Running's signature 100-mile event, held in Somerset, England. The race fuses the Flat 50 and Hilly 50 routes into one epic loop from Taunton to Minehead, largely along the Taunton–Bridgwater canal path, River Parrett Trail, and West Somerset Coast Path. Runners..

Sid Valley Ring Half Marathon, hosted by Climb South West, follows the Sid Valley Ring walking route in East Devon. The Half Marathon is an uphill-start loop through quiet lanes, footpaths and coastal scenery, climbing to 236m before descending to Sidbury, Harcombe, and the coast path with views ove..

Endurancelife Exmoor, held in the western reaches of Exmoor National Park near Martinhoe, offers four distances: 10K (6.3 miles), Half Marathon (13.3 miles), Marathon (26.5 miles), and Ultra (31.8 miles). The route is billed as one of the toughest in the Endurancelife Series, delivering a true endur..

UTMB Index

The Epona 100 is a challenging 100-mile ultramarathon held in Abergavenny, featuring a demanding 17,000 feet of elevation gain. The course offers a stunning mix of iconic trails, including Offa’s Dyke, Cambrian Way, and Beacons Way, providing runners with breathtaking mountain passes and diverse ter..

The Tenacious Ten Hour Endurance Challenge is a timed loop race on Saturday 9 May 2026 at Mynydd Troed, Pengenfford Common, near Talgarth, Powys (LD3 0EY). The event is organised by Limitless Trails and has a strict 10 hour cut-off; any lap not completed before the final horn will not be recorded...

OTT Marathon & 10 Mile Race takes place at Parkwood Dolygaer, Merthyr Tydfil, in the Brecon Beacons. The event offers two distances: a looped mountain marathon of about 26.2 miles with steep climbs and stunning views, and a 10-mile option that follows part of the same course to Checkpoint 1 before r..

Jurassic Coast Challenge is part of Ultra Challenge Series along Dorset’s World Heritage coastline. Distances: 100km, 75km, ~50km and ~25km, plus a Weymouth Marathon loop and Bridport 10K. The course runs from Corfe Castle via Swanage, Lulworth Cove and Durdle Door, with Weymouth at halfway, then on..

True Grit Trail Half Marathon takes place at Bridgend Miniature Railway Centre in Aberkenfig, Tondu, near Bridgend (CF32 0EH). The 13.1-mile route is described as epicly challenging, with mixed terrain, killer hills, a Quarry section known as the Hill of Doom, and a technical downhill forestry trail..

Rocky at 50 Run - Wales is a 7 hour time challenge held at Dare Valley Country Park in Aberdare. Runners may choose their own distance during the event, with a minimum official finish distance of 3 km. Finishers who complete at least 3 km receive a themed finisher medal, and distance pins are award..

June 2026

The VOGUM 2026 is a 40-mile ultra running challenge along the scenic Wales Coast Path, stretching from Porthcawl to Penarth in the Vale of Glamorgan. This event offers runners a chance to experience golden beaches, dramatic cliffs, and historic sites like Ogmore Castle and the famous stepping stones..

BigSea Trails (WATER) is a trail running event held on the Isle of Purbeck, Dorset, starting and finishing on the sandy Knoll Beach at Studland. Part of the Classic Element Trail Series, this race celebrates the element of water with routes that showcase stunning coastal and countryside scenery, inc..

Two Tunnels Races in Bath, UK offer a unique city-centre running experience beneath the city via the Devonshire Tunnel (408m) and Combe Down Tunnel (1672m)—the longest underground section of any UK race. The well-lit, surfaced tunnels form a flat, shared-use path starting and finishing at Brickfield..