The fate of Pedestrian Night is in the hands of the Orchard Road Business Association (Orba), a loose affiliation of companies, such as shopping mall owners and retailers, each with its own ideas and bottom lines to worry about.
A study is being done among its 111 members to gauge support for Pedestrian Night, which is when Orchard Road is closed to vehicles on the first Saturday of the month. The first Pedestrian Night was in October; the next one will be this Saturday.
Orba will then decide whether to scrap it after the six-month trial ends or make it a mainstay on the famous shopping strip.
"The decision lies squarely with Orba," says Ms Melissa Ow, assistant chief executive of Singapore Tourism Board's (STB) experience development group. The STB funds most of the event's cost and is "very open" to extending support, she said.
The cost of the event, said Orba, runs into hundreds of thousands of dollars.
Orba's decision could swing either way. Most high-end shops and those hidden in malls do not like Pedestrian Night as it pulled people out from the malls.
Drivers also shunned the event, which closes Orchard Road between Scotts and Bideford roads to traffic between 6pm and 11pm.
Supporters include cafes and fast-food joints that did swift trade. The unaffected, like beauty chain Spa Esprit Group's 10 outlets that shut before Pedestrian Night began, will also likely give the event the green light.
But it shouldn't be that difficult a decision: Pedestrian Night is already a success, plain and simple. Why? Consumers loved it.
As Ms Ow said: "If you look at some of the social media posts, people loved the idea. They loved the sense of being able to reclaim the road."
The event attracted an average of 50,000 people each time. Families came down, some with their pets. Couples danced. People posted selfies online. The event was talked about and blogged about.
Such marketing and exposure for Orchard Road are priceless.
It is unlikely to be a one-hit wonder either. An STB survey of 600 visitors over three Pedestrian Nights found that over 70 per cent would return for the event.
Ms Helen Khoo, executive director of WingTai Asia, which manages Topshop and Dorothy Perkins, gets it. The group's seven Orchard outlets - except those in Ion Orchard - saw crowds thin from 5pm. But Ms Khoo is pushing for the event to go on.
"In terms of making noise for Orchard Road, it has achieved its aim. People are publicising the road for us on social media; tourists are talking about it," she said.
"Such events create interest, get people excited about shopping again. If people think Orchard Road is the place to be, that's a good thing."
Orchard Road's glitz may be hard to beat, but its allure is being dimmed by ubiquitous brands selling more of the same, jam-packed pavements, and road barriers that make crossing the street a pain.
Meanwhile, the swanky Marina Bay Sands is gunning for more shoppers, while high-street brands like H&M are opening in suburban malls near homes, and online shopping is taking off.
Orchard Road has to differentiate itself to stay relevant. It won't be so easy.
A 2013 research paper found that 89 per cent of the estimated 200 pedestrian streets built in the United States in the 1960s and 1970s to revitalise tired city centres have failed.
The successful ones, it was found, were short stretches of road and were accessible, located in major tourist destinations, and had tenants that encourage a lot of activity such as restaurants and markets. Orchard Road has these elements but can improve.
For one thing, it can keep costs down to keep it sustainable. Instead of hiring more than 30 security guards to manage crowds and traffic, it can follow Tokyo which closes Ginza to cars using a few traffic cops with pylons.
There should be more frequent trains calling at Orchard Road during the closure.
Most shops must offer discounts and open till 11pm - when Orchard Road reopens to vehicles. During the past five events, only a handful remained open.
But more importantly, businesses must unite to create special activities so that the event does not flop, as it did in 1989.
Mr Gopinath Menon, Nanyang Technological University adjunct associate professor and a retired Land Transport Authority planner who was involved in Orchard Road's prior stab at pedestrianisation, said "there were no specific organised activities, interest waned and the scheme was suspended".
Orba has to create targeted themed events rather than just rely on stores to lug their products onto the street for sales.
At London's Regent Street, a food-themed closure had 60 food stalls lining the road. Chocolatier Godiva set up a strawberry dipping bar, and Folli Follie set out deck chairs for people to eat and relax.
Another month, Regent Street hosted a garden party, with artificial grass company Easigrass creating a lawn area, and a busking competition was held.
Orchard Road could have a pet theme one night, with pet shops setting up playpens for dogs to try new chew toys, and free grooming sessions. Another night could be for bargain hunters, and another for fashionistas.
Yes, such initiatives may not generate much revenue.
But to Orba members, I say: It's a great advertising platform. Look beyond quick sales and see that these efforts help keep Orchard Road vibrant.
If Orchard Road hums, so will your cash registers.