Orchard in the Monsoon.

Orchard Road Promenade outside Liat Towers after the rain.

Orchard Road got its name from the nutmeg, pepper and fruit orchards or the plantations that the road led to in the mid-1800s. Commercial development only began in the twentieth century, and took off in the 1970s.

Orchard Road was already cut in the 1830s, though the new road was not named in George Coleman's 1836 Map of Singapore. In the 1830s the Orchard Road area was the scene of gambier and pepper plantations. Later, nutmeg plantations and fruit orchards predominated, hence its name.

By 1846, the spread of houses had reached up to Tank Road. There were none on the left side and only three or four houses went past Tank Road on the right side of Orchard Road.

One major sight during this period was a Dr Jun tending his garden, which helped endorse the road's name. He had a garden and plantation at the corner of what is now Scotts Road and Orchard Road.

Towards the later part of the 1840s, graveyards began to appear along the road. By 1846, the Chinese had a large graveyard around what is now the Meritus Mandarin Hotel and Ngee Ann City, while the Sumatrans from Bencoolen had their burial ground where the current Grand Central Hotel stands. Later a Jewish cemetery was established; it was located where Dhoby Ghaut MRT Station is now situated, and demolished in 1984.

In the 1860s, Orchard Road had a great number of private houses and bungalows on hills looking down through the valley where the road passed through. Early in the 1890s, King Chulalongkorn, the then King of Siam, acquired "Hurricane House" in the vicinity of Orchard Road through Tan Kim Ching, the Thai Consul in Singapore. Two further pieces of adjoining property were added later and these subsequently became the site of the present Royal Thai Embassy at 370 Orchard Road.

In the early 20th century, it was noted that Orchard Road "present[ed] the appearance of a well-shaded avenue to English mansion[s]", comparable in its "quiet but effective beauty to Devonshire lanes." The Chinese called the area tang leng pa sat koi or "Tanglin market street". The Tamils refer to the road as vaira kimadam or "fakir's place", and muttu than (high ground), a reference to the hilly nature of the area.

Flash floods occurred at the road's iconic junction with Scotts Road on 16 June 2010 after 100mm of rain fell from 8 am to 11 am that morning, reportedly the worst flood at the junction since 1984. Shopping malls along Orchard Road like Lucky Plaza and Liat Towers were affected by the flood. The flood had caused some shopping mall and car park basements to be submerged in the water. Rescuers had to pull out about 70 passengers from cars and buses, as flooding shut down Orchard Road, which is lined with high-end shopping malls and tourist attractions. No one was injured.