A loop of Portland from Chesil Beach

This difficult 12.6-mile (20.3 km) hike loops around the Isle of Portland, offering a challenging experience with 1079 feet (329 metres) of elevation gain. You can expect to complete it in about 5 hours and 36 minutes. The trail features varied terrain, from long uphills on open quarry paths to technical descents on a "zig zag goat path" and narrow cliff-top sections. You will see dramatic cliffs, hidden coves like Church Ope Cove, and the iconic Portland Bill Lighthouse marking the halfway point.

Because of the demanding and varied terrain, which can be rough and wet, you should wear sturdy hiking shoes. Some paths are narrow with steep drops, and you will encounter steep ascents and descents. Be aware of recent cliff erosion in the west cliff section, where marked diversions are in place. This route requires very good fitness due to its arduous and tricky sections.

The Isle of Portland is part of the UNESCO Jurassic Coast, making this hike geologically significant. You will pass through disused quarries now reclaimed by nature, showcasing the island's history of providing white limestone since Roman times. The Fleet Lagoon, visible from the cliffs, is a Site of Special Scientific Interest known for its diverse wildlife, including many coastal birds. Towards the end, you will also walk through an eerie Sculpture Park, adding an artistic touch to the natural landscape.