Great post and very timely. You posted it in time to help my research on virtual events and tradeshows. The Woodbridge Township is considering whether it would be best to cancel / postpone the Holiday Stroll that normally is held on Small Business Saturday.

A virtual event would not be able to provide the experience of the horse & buggy ride - or similar activities that belong to the bricks & atoms world. But a virtual event opens up the possibility of better reach and "offerings" that might have overlooked earlier. 

• A drone flyby of window decorations
• Tradeshow-like setup to include Main Street and other local merchants
• Musical performances (can be delivered in Zoom breakout rooms too)
• DIY guidance for face painting at home 

Virtual events would also encourage local Main Street businesses to go online. Going online need not be restricted to hosting a catalogue and offering an online shopping cart. It could also incorporate by-appointment or scheduled open timeslots when prospects and patrons could drop in for a chat. 

One of the challenges that I can envision is the ownership, expertise and budget (time, effort, money) needed to organize this. The other side of the equation is training the merchants to convince them that it is worth their time. Then, of course, this the "minor" matter of drawing in the shoppers with an intent to spend :-) 

Meetup is expecting that virtual and hybrid events will carry on in a post COVID era. There is no reason why it should not. So even if Downtown miss the bus this year, they might want to observe others and put up an event later.