The pedestrian strip that stretches from Ion Orchard to Ngee Ann City was brightly lit with multi-coloured neon lights as the first in a series of monthly weekend events kicked off yesterday evening.
The first edition of Night At Orchard drew more than 8,500 visitors, said organiser Orchard Road Business Association (Orba).
About 30 pop-up stores offering local fashion, five food trucks and live acts lined the bustling strip. The event will run from 5pm to 10pm this weekend.
Orba said it is part of an eight-month-long pilot to revitalise the iconic road and showcase fashion, arts, street food, drinks and music with a different theme every month.
For the upcoming seven editions, the roving event will show up at different pockets of Orchard Road.
The locations are yet to be decided, but the programme line-up may coincide with special occasions such as National Day and the Singapore Grand Prix, said an Orba spokesman.
The place is crowded, but I could still move around and find a spacious place to sit and have my food while enjoying the performance.
MR JOEL LOH, a polytechnic student who was at the event.
Night At Orchard comes as larger plans are under way to transform the 2.4km stretch into a more lively and green street.
In January, government agencies announced that new retail concepts, attractions, entertainment and events will be introduced in Tanglin, Somerset, Orchard and Dhoby Ghaut to strengthen Orchard Road's position as a lifestyle destination.
Part of the road may also go car-free to connect green spaces at the Istana Park, Dhoby Ghaut Green and the open space at Plaza Singapura.
Yesterday, food trucks from local favourites such as Old Chang Kee to Michelin-starred restaurant Shisen Hanten by Chen Kentaro sold street food at up to $10.
The restaurant in Mandarin Orchard Singapore also created two items for the street event for easy consumption.
"We wanted to make our Michelin-starred food not exorbitant, but affordable. Since the customers are not going to sit in a restaurant, we are not going to charge too much," said Ms Francine Loh, marketing communications manager at Mandarin Orchard Singapore.
The shopping belt is no stranger to night street events.
From 2014 to 2016, Orba organised Pedestrian Night, where a 660m stretch of Orchard Road was closed to traffic on the first Saturday of every month.
The roads were filled with magicians, music performances, themed activities and contests.
Although the initiative attracted more than 50,000 shoppers - twice the average Saturday night footfall - to each monthly event during its first six months, the higher traffic did not translate into better business in the shopping malls.
Mr Joel Loh, 20, who was drawn to the event when he saw the food trucks, said: "I've never bought food from a food truck before and you don't get to see food trucks at many places in Singapore. "
The final-year Nanyang Polytechnic student, who was busy munching his dinner when The Straits Times spoke to him, added that he would attend future Night At Orchard events.
"The place is crowded, but I could still move around and find a spacious place to sit and have my food while enjoying the performance."