- December 18, 2025
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A nightmare is igniting in Winter Park’s public consciousness just as the sun goes to sleep, full of loud noises and interloping minstrels from places unknown. Would rampaging exotically accented drunkards stumble screaming through Hannibal Square and into the night if we suddenly legalized European-café-style on-street dining? What if we didn’t ban sidewalk musicians? Would they run rampant, bringing an ever more cacophonous vibe shaking the concrete along Park Avenue?
The answer is likely none of the above, though from the sounds of the debate inside the makeshift City Commission chambers at the Civic Center it could tear apart the conservatively gilded silk of Winter Park.
Winter Park’s image is a coveted one. Other cities outwardly look to emulate what Central Florida’s most walkable city has cultivated over the course of more than a century. They use the city as an example in their council and commission meetings. In a nation awash in all things new and fabulous, Winter Park’s upscale fashion-forward image stands as an aspirational ideal. But still, the city’s good ideas have to come from somewhere. What’s more trendy than Europe for the last 400 years or so?
Enter the idea of the street café, one borrowed — like much of Winter Park’s charm — from the walkable, visitor-friendly streetscapes of Western European cities. At Monday’s Commission meeting, the idea of closing the tiny road called Hannibal Square to cars between 5-11:30 p.m. for restaurant use was proposed for a trial run. It’s an idea with so much precedent that it predates the car by more than 100 years. Who wouldn’t want to eat outside when the weather’s nice?
Of course outside dining is already happening. Park and West New England avenues have become go-to promenades for a casual evening on the town, replete with tables spilling out onto sidewalks for those who prefer more naturally conditioned air and a street-side ambiance.
Such has been the case on both sides of Hannibal Square, along sidewalks filled with al fresco enthusiasts who choose to eat ever so close to the street, but not quite.
But the cries of potential horrors to befall the city’s streets still rang out Monday, portending restless nights nearby in Hannibal Square neighborhoods. All of this was still perfectly possible before the road closed, since diners could still eat outside if they pleased. They could still make just as much noise, which in buttoned-down Winter Park has always been more hushed than the worst-case scenario of bustling downtown Orlando.
It could be an issue of volume, both in customers and noise. The more table space that nearby restaurants could use, the more potential for noise on the street. But as has already been pointed out by city staff, the nearest home is 200 feet away.
Mixing into the quiet versus quaintness argument at Monday’s meeting, the fear of sidewalks overrun with street performers also caused a stir, amid more legitimate cause for concern over noise levels and the possibility of loud, panhandling musicians-cum-street urchins scaring off customers.
Should there exist some vetting or permitting mechanism for nighttime street performers along Park Avenue? Local musician John Holley already has one: ask the store’s owner for permission to play out front. His answer has invariably been yes, though as was pointed out at the Commission meeting, there is some accounting for taste. Is an accomplished, trained musician just as welcome as a paint bucket drum circle? That question remains to be answered, as the Commission passed the decision whether to regulate street performers back to city boards to come up with a concrete plan.
Some play for the love of music, or to get noticed, as has been the case with Holley. Playing for change brings with it a mixed bag of true musicians along with the occasional drunken trumpeter.
Whether street dining and sidewalk musicians get to stay in Winter Park remains to be seen. The former seems likely. The latter may come down to a question of taste. Both have their pluses, but no one wants to see Winter Park’s laid back but conservative image tarnished like well-worn brass.