Isle of Portland
Trail Running Calendar near Isle of Portland 2026-2027
Explore the top trail runs near Isle of Portland for 2026-2027! We've gathered 30 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
An off road ultramarathon from Maiden Newton of about 35.9 miles with roughly 1,300 m of ascent, passing hillforts and coastal views. Six aid stations offer water and cake, GPX files and maps are provided for navigation.
A twilight off-road 10 km through a reputedly haunted parish of Dorset, starting and finishing in the park in front of Eastbury House. The route passes Chettle woods, Bloody Shard Gate and Chettle Long barrow.
A 7 mile chip timed trail race around The Blue Pool in Dorset on 7 November 2026. The route passes woodland, hills, heath and ridges and includes a capped canicross category; entry includes pool access for one adult and up to two children.
An evening trail run from Corfe Castle with three routes across muddy heath and woodland, lit by headtorches and offering ridge views of Purbeck.
A trail event through 600 acres of Charborough Estate woods offering a 10K, a double-loop half marathon or a two-person relay on 29 November 2026.
December 2026
Coastal 10 mile and 10K runs from Hengistbury Head along Bournemouth seafront with chip timing, water stations and a finisher medal.
A level 19 km trail race along a converted railway through the River Stour valley. The family oriented event has marked route, aid stations, a canicross option and prebooked transport between start and finish.
A charity 5 km fun run and 2 km kids run on Weymouth Beach on 20 December 2026 supporting The Will Mackaness Trust youth projects.
February 2027
Self-navigation coastal trail run on Portland offering marathon (two loops), half and 10k, mandatory kit and GPX navigation, entries capped at 500.
March 2027
A measured 10 km charity run in Weymouth organised by MCC Promotions. The mostly flat road course runs from Bowleaze Green toward Pleasure Pier and includes on day registration, race facilities and prizes.
Trail races and a charity walk at Lulworth Estate near East Lulworth on 7 March 2027, with 5 km and 10 km routes, chip timing, medals and post-race treats.
Coastal trail runs from Swanage seafront to Corfe Castle with three distances, firm chalk and sandy tracks, on-course support and a vintage steam train return.
A countryside challenge from Cerne Abbas offering 20 or 30 mile routes across Dorset downland and river valleys with checkpoints and an 11 hour time limit.
Three consecutive long distance days along the Jurassic Coast from Charmouth to Shell Bay. Daily support includes checkpoints with food and drinks, transport from HQ, GPS tracking, medical cover and a bespoke finisher medal.
A 40 mile coastal ultra from Abbotsbury to Lulworth Cove along the South West Coast path, featuring rugged terrain, checkpoints every 10 to 20 km, compulsory safety kit and GPS tracking; ITRA and UTMB recognised.
April 2027
A Backyard Ultra on Portland where runners repeat a 6,706 m (4.167 miles) loop each hour until one remains; camping, chip timing and on-site support are included.
May 2027
Multi distance trail event along the Jurassic Coast from Corfe Castle to Bridport with support, rest stops, GPS tracking, camping and finishers kit.
The Pretty Muddy 5 km obstacle course at Baiter Park, Poole on 29 May 2027 runs across grass and tarmac with staggered wave starts every 15 minutes. Participants must be 13 or older and there is a minimum fundraising target.