Trail Running calendar near Chepstow 2025-2026

Run the Sid Valley Ring Half or Third Marathon on 9 May 2026 and soak up coastal, woodland and country lane scenery. Choose 22 km or 13.5 km, expect hills and mud, and help maintain the trail with your entry.

Take on Endurancelife Exmoor on 9 May for sweeping moorland, cliffs and wooded combes with routes from 10K to an Ultra, featuring stiff climbs and stunning coastal views. Fully marked courses, electronic timing and a finishers medal make it..

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.

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.

Join the Hardy Half in Dorchester for scenic trail running with a 5 mile option or a challenging half marathon with about 1400 ft of climbing. Finish at Dorchester club where an event village, entertainment and local fundraising await.

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 or walk the stunning Jurassic Coast from Corfe Castle to Bridport, passing Durdle Door, Lulworth Cove and Chesil Beach. Distances from 10 km to 100 km with full support, camping options and a finisher medal.

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.

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.

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 Grand Union Canal Race, a nonstop 145 mile ultra from Birmingham to Little Venice along scenic towpaths. Limited to 100 starters with a 45 hour limit, it welcomes supported and unsupported runners for a true canal challenge.

Take on the Rocky at 50 Run Wales, a relaxed 7 hour time challenge at scenic Dare Valley Country Park where you pick your distance from a 3 km minimum up to 50 km. Finishers earn themed medals and enjoy tasty aid station treats.

Run the scenic Southampton Common, winding through woodland, ponds and parkland with half marathon, 10K, 5K and junior races. Enjoy marshalled routes, a lively event village with food and partner stalls and optional event T shirt.

Run the Brecon Beacons at Midnight Mountain Marathon on June 6, 2026, starting in daylight and finishing under the stars, so some may need a torch. Take part in Marathon, Half Marathon or Bergen pack races and earn a medal and a mug of tea.

Join the Divorce Day Defib Fundraiser for a fun, scenic run from Coalport Village Hall along the Silkin Way and over Ironbridge. Choose 8, 16 or marathon distances and embrace fancy dress with top hats and tiaras to boost spirits.

Tackle 40 miles of the Wales Coast Path from Porthcawl to Penarth, passing golden beaches, cliffs and Ogmore Castle. No time limits and strong support let you relax and earn a Pegasus medal.

Explore the Purbeck coast with BigSea Trails WATER, a single lap trail that starts on Knoll Beach and takes in Corfe Castle, Kimmeridge Bay and Old Harry Rocks. Expect rugged coastal scenery and varied terrain for a memorable day on the tra..

Run through two lit railway tunnels beneath Bath on routes from short fun runs to ultra distances. Starts and finishes at family friendly Brickfields Park and each entry supports Sustrans, making it a memorable community day out.