^ Raffles Hotel (1) opened in an old bungalow facing the beach on 1 Dec 1887. The main building was opened in 1889, established by 3 Amenian Sarkies brothers, Raffles Hotel became THE place in Singapore for entertainment, dining and accommodation before the WWII. Today it includes a shopping arcade, a museum, romantic courtyards and Jubilee Hall, the Victorian-style theatre that is a popular venue for film screenings and performances.
^ CHIJMES (2) (pronounced "chimes") was once the Convent of the Holy Infant Jesus (CHIJ) established in 1854.The Convent of the Holy Infant Jesus was a school founded by Father Jean-Marie Beurel and French nuns in 1845. It was relocated in 1983. In 1995, the area was converted into a commercial complex known as CHIJMES.
^ Cathedral of the Good Shepherd (3) was built between 1843 and 1847 and was consecrated a Cathedral on 14 February 1897. Built at a cost of $20,000, this Roman Catholic cathedral takes the form of a crucifix in the Renaissance style. The cathedral became an emergency hospital during WWII. This Cathedral's architecture was inspired by two English churches of the time, St Paul's in Convent Garden and St Martin-in-the-Fields. It was built to meet the needs of the growing Catholic population in Singapore.
^ Former St Joseph's Institution (4). Transformed from a 19th century mission school to a dynamic institution of multi-cultural 20th century art museum. Designed by Brother Lothaire, a French priet-architecture, and marked the beginning of Catholic boys' school education began. In 1987, the school moved to a larger building in Malcom Road but the statue of St John Baptist de la Salle by Cesare Aureli still remains in the Singapore Art Musem.
^ The Singapore Art Musem (5). The restoration of the building to an art museum started in 1992. During restoration, the original design of the building was respected. At the same time, all the requirements for a state-of-the-art museum was integrated into the building. The three historical structures, the Central building, the Anderson block and the Chapel were retained. The Singapore Art Museum is the nation’s premiere venue for international arts exhibitions.
^ The Cathay Building (6). Being the first air-conditioned theatre in Singapore, people from different communities had visited this landmark which has great significance. It was home to the British Malaya Broadcating Corporation until the Japanese invaded Singapore in 1942 and the building was used as the Japanese Propaganda Department HQ. The history of this landmark educates Singaporeans to be psychologically strong in any emergency and unites us against anybody who tries to conquer us.
Look out for the WWII memorial plaque (above right picture) facing Handy Road.
^ MacDonald House (7) was built in 1949 for the Hong Kong & Shanghai Banking Corporation and was the first large building after the war. One of the first high-rise buildings in Orchard Road, it housed mainly British, American and Australian companies. In 1963, during the Indonesia Confrontation in Singapore, a bomb planted in the building by Indonesia terrorists and killed several people.
^ Istana Park (8) is situated directly opposite the Istana, the official residence of the President of Singapore, the park was designed by Ren Matsui, a prominent Japanese landscape architect. It features a unique reflecting pool and the Festival Arch, a 16m high structure of concrete and stainless steel.
^ The Orchard Road Presbyterian Church (9), a.k.a. Greja Kechil and the Scots Church, is the earliest Presbyterian church in Singapore. Built in 1877, it currently runs services in multiple languages.
^ The YMCA Building (10). The Singapore Chapter of the YMCA acquired this site in 1909. During the WWII, the building was used by the Kempeitai, the Japanese Military Police. The interrogation and torture of many innocent civilians took place here. In 1981, the old building was torn down and rebuilt to cater for the Association's numerous activities.
^ Singapore History Musuem (11) showcases some of the most valuable displays concerning Singapore's history. Designed by McCallum and McNair, the museum was called the Raffles' Library and Museum - Singapore's first museum and library. It was renamed to national Museum in 1960. This museum focuses on Singapore's political and social history.
^ The Fort Canning Park (12) is located at Fort Canning Hill. The park belongs to the British to hold its Government Office. It is also a strategic British battleground command centre during WWII as it overlooks the Singapore Town. Many underground bunker and cannons are built here. This history connected to the park during WWII educates the public about what the British did during the war, and how it is important to be united during times of emergency. Now, cultural shows, concerts and events are held here.
^ Peranakan Museum (13), formerly known as Asian Civilisations Museum @ Tao Nan. It focus on the distinctly local Peranakan culture. This building was formerly Tao Nan School established in 1906 by the Hokkien Clan Association for the local Chinese
^ National Archives of Singapore (14). Formerly the Anglo-Chinese Primary School, the National Archives of Singapore was located to this site in 1997. There is a wealth resources, including wonderful old photographs of Singapore, oral history tapes, old maps and documents.
^ Singapore Philatelic Musuem (15) was originally part of the Anglo Chinese Primary School which used to house the headquarters of the Methodist Church and the Methodist Book Room. This museum houses a unique collection of stamps and first day covers.
^ Armenian Church (17) is regarded as early Singapore architect George Coleman's masterpiece. Modelled after the Mother Church in North Armenia, this is Singapore oldest church. It was built in 1835 and dedicated to St Greogory, the illuminator. Take a walk in the peaceful memorial garden where pioneers of the Armenian community are buried
^ The Central Fire Station (18) opened in 1909, this station is Singapore's oldest fire station. Today, it houses the Singapore Civil Defence Force. the Fire Bridage's successor. The station is open to the public on Saturdays morning.
^ The Ministry of Information and the Arts (MITA) (19). The old Hill Street Police Station was built in 1934. The largest government building of its time, this 6th storey building with its arcades and central courtyards was designed in the neo-classical style then fashionable in England.
^ St Andrew's Cathedral (20) has its origin in the St Andrew's Church which was designed by Coleman and was completed in 1834. In 1852, it was declared unsafe and a new building was erected. This became the present St Andrew' Cathedral. A window inside this oldest Anglican house of worshipin Singapore commemorates Raffles, regarded as the founder of modern Singapore. it is named after St Andrew, patron saint of Scotland. Designed in early English Gothic style by Colonel Ronald Macpherson, it was built by Indian convict labout. The Cathedral's glossy white exterior is the result of using Madras Chunam, a mixture of shell lime, egg white and sugar.
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