On the east side of that charming, close-knit enclave, however, lies an impoverished swath of rundown homes, shuttered storefronts and vacant factories that harken to the city's industrial heyday.
For two nights, protesters torched a half dozen businesses, smashed cars and and hurled rocks at police on Milwaukee's north side.
People who live here, both black and white, have long known this. It's only now, however, that authorities -- and the nation -- are waking up to it.
"These young people don't have much, and they're treated like they don't have much," said state Representative David Bowen, a man who isn't much older than many of those protesting.
"We have written them off."
Curfews and prayer alone won't solve the issues
The weekend violence was largely confined to Sherman Park, a predominately black neighborhood on the city's north side. In other parts of Milwaukee, however, life seemed to go on as usual.
"Other than the people who live in the community, everyone else knows what's happening because of the news," Jackson said.
The site where protests raged this weekend now smolders. At times on Monday night, it seemed like a wake. People came to pray, to cook food, to raise money for Smith's family.
At other times, it seemed like the neighborhood would explode again as cops in riot gear pulled up in vans and pounced on young men.
Police erected a temporary plastic barrier around Sherman Park, which was also the site of violent clashes between police and dozens of young men in June after a city bus was vandalized. The park is now closed from 6 p.m. to 6 a.m.
But resolving Milwaukee's problems will take more than curfews and prayer.
"How do we lift our young men out of the cracks?" asked Valencia Morgan, 52, who stood outside Sherman Park with her daughter and her grandchildren.
"They come from homes where mom and dad are on drugs," she said. "Kids are growing up by themselves, taking care of their siblings."
She brought with her six dozen freshly baked cupcakes and a handwritten sign that read: "Free cupcakes, free hugs!!!"
A pair of white police officers in a van took up the offer, stepping out of their the van to eat a few and exchange hugs with the group.
"I know they are misunderstood," said Morgan, who is black. "I'm happy they felt comfortable enough to stop."
One of the worst cities for racial inequality
The reaction to Smith's shooting death by police only highlighted deeply rooted issues here
"The killing was simply the spark in a very combustible situation," said Reginald Jackson, a teacher and community activist who lives blocks from the unrest.
On virtually every indicator of racial inequality, Milwaukee consistently ranks among the worst five cities
in the country.
Milwaukee's racial tension goes back decades, but it's largely tied to the collapse of its industrial economy. When manufacturing jobs were cut, the segregated black community was hurt disproportionately as many people began moving to the suburbs.
Over the years, the city has been a flashpoint for a number of racially charged political battles over voter ID laws, affordable housing and school reform. About 70% of Milwaukee's black children attend hyper-segregated schools -- nearly the same levels as 1970.
The city, which one of the poorest in the nation, has also fought for two decades over a never-built regional rail transit system.
Blacks are overwhelmingly concentrated in the city and a few nearby suburbs, while the surrounding suburban counties are less than 2% black and less than 5% Hispanic. Because there is almost no public transportation between these parts of Milwaukee, the metro area remains racially, economically and politically divided.
Standing near the burned down gas station Monday night, moments after a tense confrontation between protestors and heavily armed officers, Rep. Bowen said the city "needs to listen" to this community's "calls for help."
"A big portion of the population is starting to give up hope that Milwaukee will ever change," he said.
Where it's easier to buy a gun than find a job
Nealena Poe, 19, walked by the charred remains of the BP gas station Monday evening and joined a group of strangers holding hands. They bowed their heads and said a prayer behind the yellow police tape.
"There are killings every day, Little children are dying. There are no jobs. And there are some racist cops," she said. "But we're killing each other, too."
Asked if she planned to attend the protests later, she shook her head. "I have a child to live for."
Milwaukee is the eighth most violent city in the US. There were seven violent crimes for every 1,000 people in 2015, according to FBI statistics. It had 145 homicides last year.
So far this year, 83 homicides have been reported. Five of those occurred between Friday and Saturday.
James Miller, 54, said it's easier to buy a gun in Sherman Park than to find a job or a decent place to eat. He said more than a dozen young men, armed with handguns, rushed past his house on their way to the protests Sunday night.
"The kids, they have more weapons than the cops," said Miller, who has lived in Sherman Park for 20 years. "They don't have the skills to navigate life without violence, which rules here."
Alderman Khalif Rainey and others have said the street violence stems from deep-seated inequities, unemployment and lack of educational opportunities.
"No one can deny the fact that there are problems, racial problems in Milwaukee, Wisconsin, that need to be rectified," Rainey said.
Smith's death was just the latest flashpoint in a simmering city. Last year, protesters took to the streets after the district attorney declined to prosecute a white police officer who fatally shot a mentally ill man named Dontre Hamilton
The area, according to Rainey, has been a "powder keg" for unrest.
"The black people of Milwaukee are tired; they are tired of living under this oppression," he said. "This is their life."