Orchard Road Presbyterian Church

Wesley Methodist Church is the oldest Methodist church in Singapore. It is the second Methodist Church to be built in Singapore after the Methodist Episcopal Church at Coleman Street which subsequently became a school hall. It is located in Fort Canning Hill.

Amber Mansions was a shopping centre and residential building located at the curve between Orchard Road and Penang Road in what is currently known as Dhoby Ghaut, Singapore. Constructed in the 1920s, the shopping centre was one of the first shopping centres in Singapore.

Fort Canning Tunnel (Chinese: 福康宁隧道; pinyin: Fúkāngníng Suìdào), abbreviated as FCT, is a vehicular tunnel in the Central Area of Singapore. Besides the utilisation of relatively new engineering techniques, special care was taken to minimise impact on the environment of the surrounding Fort Canning during construction. The original contract for the FCT project was awarded to Sato Kogyo for S$25.95 million.The FCT was one of four Technical Tours organised by the Land Transport Authority and Association of Consulting Engineers on 29 September 2006 during the World Roads Conference 2006 held in Singapore.

The YMCA Building is the current headquarters of YMCA of Singapore. It also operates a hotel under the name of YMCA @ One Orchard.

The Kempeitai East District Branch was the headquarters of the Kempeitai, the Japanese military police, during the Japanese occupation of Singapore from 1942 to 1945. It was located at the old YMCA building, at the present site of Singapore's YMCA Building on Stamford Road. Opened in 1911, the distinctive Art Deco YMCA building was the site of interrogation and torture of many innocent civilians, including the war heroine Elizabeth Choy. After the war, the Singapore government erected several memorials with some at the former massacre sites. In 1995, the former site of the old YMCA building was gazetted by the National Heritage Board as one of the eleven World War II sites of Singapore.

The Cathay is a mixed-use 17-storey cinema, shopping mall and apartment building located at Handy Road and Mount Sophia in the Museum Planning Area of Singapore.

The Cathay Building (simplified Chinese: 国泰大厦; traditional Chinese: 國泰大廈; Malay: Bangunan Cathay) was opened in 1939 by Dato Loke Wan Tho as the headquarters for the British Malaya Broadcasting Corporation. Located at 2 Handy Road in the Museum Planning Area of Singapore, the building was most known for its air-conditioned theatre known as the Cathay Cinema, then a technological marvel and the first to be built in Singapore. Cathay Building was the first skyscraper in Singapore and tallest building in Southeast Asia at that time.

Dhoby Ghaut () is a place in Singapore that often refers to the Dhoby Ghaut MRT station, a major interchange station on Singapore's Mass Rapid Transit network connecting the North-South Line, North East Line, and the Circle Line. As a place, Dhoby Ghaut lies along the eastern end of Orchard Road. There is a shopping mall above the MRT station called Plaza Singapura.

The National Museum of Singapore is a public museum dedicated to Singapore's art, culture and history. Located within the country's Civic District at the Downtown Core, it is the oldest museum in the country, with its history dating back to when it was first established in 1849, starting out as a section of a library at the Singapore Institution as the Raffles Library and Museum. After several relocations over the next few decades, the museum moved to its current permanent site at Stamford Road in 1887. Between 1993 and March 2006, it was briefly known as the Singapore History Museum, before it returned to its present name that was first given in 1965. The museum preserves and interprets Singapore's social history, exploring the key events and people that have shaped the nation. Over the centuries, the National Museum of Singapore has expanded and undergone various expansions and renovations, with the most recent being a three-and-a-half-year restoration that was completed in 2 December 2006, and was officially reopened on 7 December 2006 by former President of Singapore S. R. Nathan and the Minister for Information, Communications and the Arts Lee Boon Yang. The Singapore History Gallery opened on 8 December that same year. It is one of six national museums in the country; the other five being the two Asian Civilisations Museums at Empress Place Building and Old Tao Nan School respectively, the Singapore Art Museum, Peranakan Museum as well as the National Gallery Singapore. The National Museum of Singapore is also one of the country's national monuments, having been designated as such in 1992 by the National Heritage Board. It is one of the largest museums in Asia. Admission to the National Museum of Singapore is complimentary for Singaporean citizens and permanent residents.

The MacDonald House is a historic building and monument in Singapore, located at Orchard Road in the Museum Planning Area, within the Central Area. It was the first building to be fully air-conditioned in Southeast Asia. Located a short distance from the Istana, it was the last remaining office building in facing brick in the central area. Initially built for a bank, it continues to function as a banking hall (albeit for a different bank) today, although it is better known as the site of a bombing attack in 1965 at the height of Indonesia–Malaysia confrontation.

The MacDonald House bombing was a terrorist attack on the MacDonald House building in Orchard Road, Singapore. Occurring just a few months before Singapore's expulsion from Malaysia, the nitroglycerin bomb was planted by Indonesian saboteurs during the period of heightened Indonesia–Malaysia confrontation, also known as the Konfrontasi. The explosion killed three people and injured at least 33 others. At the time, the building was used by HSBC.During this period, Indonesia openly opposed the formation of Malaysia, perceiving in its view that it was merely a neo-colonial state, especially for the British. Indonesian saboteurs mounted a campaign of terror in Singapore, then a major state and city within Malaysia. There were a total of 37 bombings from 1963 to 1966. They were trained to attack military installations and public utilities. However, when the saboteurs failed in their attempts to attack these installations that were heavily guarded, they set off bombs indiscriminately to create panic and disrupt life in Singapore as well as in Malaysia. By 1964, bomb explosions became frequent. To help the police and army defend Singapore from these attacks, a volunteer force was set up. More than 10,000 people signed up as volunteers. Community Centers served as bases for the volunteers to patrol their neighbourhoods. In schools, students underwent bomb drills. The government also warned Singaporeans not to handle any suspicious-looking parcels in the buildings or along streets. Despite the efforts of the British, small groups of saboteurs managed to infiltrate the island and plant bombs. By March 1965, a total of 29 bombs had been set off in Singapore.

Dhoby Ghaut MRT station is an underground Mass Rapid Transit (MRT) interchange station on the North South, North East and Circle lines in Singapore. Located beneath the eastern end of Orchard Road shopping belt in Dhoby Ghaut, Museum Planning Area, the station is integrated with the commercial development The Atrium@Orchard. The station is near landmarks such as The Istana, the MacDonald House, Plaza Singapura and Dhoby Ghaut Green. Dhoby Ghaut station was part of the early plans for the original MRT network since 1982. It was constructed as part of Phase I of the MRT network which was completed in 1987. Following the network's operational split, the station has been served by the North South line since 1989. To construct the North East line platforms, which were completed in 2003, the Stamford Canal had to be diverted while excavating through part of Mount Sophia. The Circle line platforms opened in 2010 along with Stages 1 and 2 of the line. Currently the only triple-line MRT interchange station in Singapore, Dhoby Ghaut station is one of the deepest and largest stations, with five underground levels. Its deepest point is at 28 metres (92 ft) below ground. The station features many forms of artworks, three of them under the Art-in-Transit scheme in the North East line and Circle line stations, a set of Art Seats at the Circle line platforms, and an art piece above the North South line platforms.