Royal Naval Hospital, Portland

Merchant's Railway was a horse drawn and cable operated incline railway on the Isle of Portland, Dorset, England, built for the stone trade on the island. It was the earliest railway in Dorset, opening in 1826. The railway ran two miles from many working quarries at the north of Tophill, along the edge of Verne Hill, to a pier at Castletown, from where the Portland stone was shipped. It was in operation from 1826 to 1939. Since becoming disused the original path of the railway has become a popular public footpath.

Castletown is a small village in Underhill on the Isle of Portland in Dorset. It is located close to Fortuneswell, on the shores of Portland Harbour, and includes a sandy beach, as well as one of Portland's notable highlights; Portland Castle, while the Weymouth and Portland National Sailing Academy is also located nearby. As with the rest of Portland's villages and settlements, Castletown has been designated as a conservation area, as it is a place of special architectural and historic interest. Underhill, incorporating Castletown and other settlements became designated in 1976 with boundary extensions in 1997 and 2000.

Portland Castle is an artillery fort constructed by Henry VIII on the Isle of Portland, Dorset, between 1539 and 1541. It formed part of the King's Device programme to protect against invasion from France and the Holy Roman Empire, and defended the Portland Roads anchorage. The fan-shaped castle was built from Portland stone, with a curved central tower and a gun battery, flanked by two angular wings. Shortly after its construction it was armed with eleven artillery pieces, intended for use against enemy shipping, operating in partnership with its sister castle of Sandsfoot on the other side of the anchorage. During the English Civil War, Portland was taken by the Royalist supporters of King Charles I, and then survived two sieges before finally surrendering to Parliament in 1646. Portland continued in use as a fort until the end of the Napoleonic Wars in 1815, when it was converted into a private house. Fresh concerns over invasion led to the War Office taking it over once again in 1869, but the castle was not rearmed and was instead formed accommodation for more modern neighbouring fortifications. During the First and Second World Wars it was used as offices, accommodation and as an ordnance store. In 1949, the War Office relinquished control, and in 1955 it was opened to the public by the state. In the 21st century it is managed by English Heritage and operated as a tourist attraction, receiving 22,207 visitors in 2010. Historic England consider the castle to form "one of the best preserved and best known examples" of King Henry's forts.

Victoria Gardens is a public garden, located at Underhill, Isle of Portland, Dorset, England. It is found close to Fortuneswell village and overlooks both Victoria Square and Chiswell. The gardens, which were created to mark the 1897 Diamond Jubilee of Queen Victoria, have remained a focal point since their opening in 1904.The gardens are made up of grassed and formal bedding areas, with a large rockery running along its centre. There is a children's play area, tennis courts and a bowling green managed by the Portland Victoria Bowls Club.

Royal Manor Theatre is a theatre located in Fortuneswell, Isle of Portland, Dorset, England. Formerly a Methodist chapel, the building was later converted into the Royal Manor Theatre, which opened in 1978.

Underhill is the name given to the area of very steep land, at the northern end of the Isle of Portland in Dorset, England, which contains the villages of Chiswell, Castletown and Fortuneswell. The remaining part of the island is known as Tophill. The geology of Underhill is different from Tophill; Underhill lies on a steep escarpment composed of Portland Sand, lying above a thicker layer of Kimmeridge Clay, which extends to Chesil Beach and Portland Harbour. This Kimmeridge Clay has resulted in a series of landslides, forming West Weares and East Weares.

Chiswell , sometimes , is a small village at the southern end of Chesil Beach, in Underhill, on the Isle of Portland in Dorset. It is the oldest settlement on the island, having formerly been known as Chesilton. The small bay at Chiswell is called Chesil Cove, and the beach promenade and sea wall which form Chiswell's coastal defences are a prominent feature. The village occupies much of the flat land close to sea level adjacent to the beach, and is distinguished from the adjoining village of Fortuneswell which occupies the steeper hills and streets above. At the northern entrance to the village is the 19th-century development of Victoria Square, which forms a roundabout on the main A354 road onto the island. As with the other villages and settlements on Portland, Chiswell was designated as a conservation area as part of Underhill in 1976, as it is a place of special architectural and historic interest. The village has been maintained by the Chiswell Community Trust since 2003.

Victoria Square is a public square on the Isle of Portland, Dorset, England. Developed in the 19th century, it is situated at the entrance to Portland, close to Chesil Beach, Osprey Quay, and the small fishing village of Chiswell.

St. John's Church (also known as St John the Baptist Church) is an Anglican Church of England church in Fortuneswell, on the Isle of Portland, Dorset. It was built between 1838–40 and has been a Listed Grade II building since January 1951. The churchyard walls, gate piers, railings, and steps of St. John's Church, dating from 1839–40, became Grade II Listed in September 1978. At this same time, two headstone monuments, about 5 metres north east from the west tower of the church became Grade II Listed.Designed by Edward Mondey or Charles Wallis, the church cost £2,315. Built of Portland stone, the church has a Gothic design in Commissioners' Early English style. It has also been described as Norman in its architecture.The church remains active, as part of the Portland Parish - a host of three churches; St John's Church (St John the Baptist), All Saints Church and the Avalanche Memorial Church (St Andrew's Church).

Conjurers Lodge is a former Methodist chapel and workshop on the Isle of Portland, Dorset, England. It is located on the corner of Clements Lane within the village of Chiswell. Established in 1816, the chapel was in use for a decade. The lodge has been Grade II Listed since 1993 and is described as a "rare surviving example of its kind" on the island.Following rumours of local Methodists believing in witchcraft, investigations by Rev. Francis Derry led to 50 members of Portland's society being expelled in 1816. This group then established a chapel on the upper floor of a workshop in Chiswell, which gained the name Conjurers Lodge. It remained in use for ten years until 1826, when the Methodist society was united once again. Portland Joinery later used the building as a workshop from 1973 to 2003.

Chiswell Walled Garden is a community walled garden, located on the Isle of Portland, Dorset, England. It is found in the village of Chiswell, close to Chesil Beach, within the remaining ruins of an old Jacobean house. The garden was created between 2001-06 by the Chiswell Community Trust, with funding from Countryside Agency under their Doorstep Green Initiative. It is maintained by volunteer members of the trust and is open to the public.

The Portland Mulberry Harbour Phoenix Units are two reinforced concrete caissons, built as part of the artificial Mulberry harbours that were assembled as part of the follow-up to the Normandy landings during World War II. Out of a total of 148 produced units, two units still remain at the Isle of Portland, in Dorset, southern England. They are located at Portland Harbour, close to Queen's Pier. The two units became Grade II Listed in 1993.