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Geylang Road was one of the earliest roads built in Singapore.

The earliest roads laid in modern Singapore after its founding in 1819 were laid out in an orderly manner as detailed in the Jackson Plan of 1822, in keeping with Sir Stamford Raffles's directions. A grid-system was adopted for the town area, with roads for carriage 16 yards wide, and that for horses at four yards. Pedestrian paths along the road sides will be two yards wide allowing room for two to walk abreast and giving rise to the famous Five foot ways which came to be associated with the sheltered walkways along roadside shophouses.

These roads were fairly advanced for the time, with Macadam-surfacing already used on High Street, Singapore in 1821, for instance. Roads were also constructed into the rest of the island, although they are usually unsurfaced. By 1842, Changi Point in the eastern tip was accessible via an extension of Geylang Road, while Pasir Panjang Road has reached Jurong River in the west. The Bukit Timah Road has also been extended to Kranji in the north by 1845, in proximity to where the Johor-Singapore Causeway will be built almost 80 years later in 1924. Still, only about 340 kilometres of road were built in a century after 1820, compared to over 2,000 kilometres built in four decades after 1965.

As is the case in other urban areas of its time, the earliest modes of road transport were via horse-drawn carriages, although ponies were used even earlier. Introduced into Malaya during the era of the Dutch East Indies where the Batak ponies from the Sultanate of Deli in Sumatra, often called palonguins or later, gharries, although they proved too small for larger carriages introduced by the Europeans later. Driven as fashion statements for the social elite, the Europeans would parade their carriages around the Padang, soon joined by their affluent Chinese and Arabic counterparts. So important were these parades in the networking opportunities they provide, that private merchants were known to volunteerily sponsor the construction of public roads to speed up road construction. Collyer Quay, for example, was noted to be constructed purely via private funding.

The most well-to-do would typically own their carriages and horses, often employing native Indian servants (popularly known as Syces) to maintain them. Carriages for hire soon became available as well, with hackneys and gharries being the earliest forms of taxis in Singapore. Other uses of pony-drawn carriages include the Singapore Fire Brigade, the predecessor of today's Singapore Civil Defence Force.

• List of bridges in Singapore
• List of expressways in Singapore

• Ilsa Sharp, (2005), SNP:Editions, The Journey - Singapore's Land Transport Story. ISBN 981-248-101-X