Portland
Trail Running Calendar near Portland 2026-2027
Explore the top trail runs near Portland for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail running at Charborough Estate on 29 November 2026 with 10K, half marathon and a two person relay through 600 acres of ancient woodland.
December 2026
Coastal 10 Mile and 10K runs from Hengistbury Head along Bournemouth seafront via Boscombe Pier, chip-timed with water stations, a finisher's medal and on-course support.
A level 19 km trail on a former Somerset and Dorset railway with two aid stations, marked route and a festive finish; dogs and buggies are welcome.
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.
January 2027
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 charity trail event at Lulworth Estate on 7 March 2027 offering 5 km and 10 km routes, dogs welcome and post-race cakes.
Coastal trail run from Swanage to Corfe Castle with three distances, firm chalk and sandy trails, chip timing and a vintage train return for an extra fee.
A dog-friendly obstacle course at Upton Country Park on 20 March 2027 with 2.5 km and 5 km options, music, a doggy disco and fundraising for Lewis-Manning Hospice Care.
An LDWA challenge from Cerne Abbas offering 30 or 20 mile routes across Dorset downland with checkpoints, refreshments, a finish meal for finishers and an 11 hour time limit.
Three marathons in three days along the Jurassic Coast, with checkpoints, medical cover, transport from Portland HQ and required personal kit.
A 40 miles coastal ultra from Abbotsbury to Lulworth Cove along the South West Coast Path with mandatory kit, checkpoint support, GPS tracking, and medical cover.
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
Trail races in Dorchester on 9 May 2027 with two distances (5 miles and 13.1 miles), off-road routes, aid stations and fundraising for local charities.
Multi distance trail event along the Jurassic Coast from Corfe Castle to Bridport with support, rest stops, GPS tracking, camping and finishers kit.
A muddy 5 kilometre obstacle event at Baiter Park, Poole with staggered wave starts, on-course obstacles and on-site facilities; main event for ages 13 and over.