The week of Thanksgiving, Jason Puskar wasn’t worried about brining and roasting the turkey.
He was worried about his alley’s fate that winter, putting the final design touches on a flier reminding neighbors in the 2900 blocks of North Stowell and Prospect avenues to chip in for private snow-removal service for the alley behind their homes.
In Milwaukee, a city where plows and salt are part and parcel of winter, only roads receive these services. Residents are responsible for clearing alleys and sidewalks. And that’s not uncommon; Chicago, Detroit and Cleveland – three other Midwestern cities notorious for snowfall – also do not plow alleyways. However, it’s not unheard of, as residents of both Minneapolis and Pittsburgh will tell you.
While Milwaukee’s Department of Public Works declined to comment for this story, common reasons cities give for not providing city-contracted snow-removal services are the risk of damaging garages or blocking cars in, as well as technicalities: in some cities, alleys are not public rights-of-way as sidewalks and roads are. That doesn’t apply in Milwaukee though, as alleys are officially public right-of-way.
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Many Milwaukee suburbs remove snow from alleys, including West Allis, where according to its website the city’s Snow and Ice Control service, “contingent on staffing availability, does a one-time pass-through to treat and plow approximately 42 miles of alleys when snowfall is greater than 2 inches.” Wauwatosa also plows its alleys.
But in Milwaukee, residents living adjacent to alleys must take it upon themselves to hire their own service. Puskar’s three-person team treats it like a business. Puskar handles email and flier outreach, another neighbor sends out bills and manages finances, and another hashes out the plow service’s contract. They collect neighbors’ fees in a joint account at a local bank, in part to avoid suspicion any of them are skimming.
“We have high participation,” says Puskar, “about 95% [not counting rental properties].” This adds up to 30 houses. Each address pays $20 through check or Venmo for an entire season of snow removal in the alley, with the plow clearing every snowfall of 2 inches or more. If a household has more than one car that uses the alley, it’s an additional $20.
It’s a lucrative source of business for plow services. Dan Wenzel, owner of D&B Lawn Service in Oak Creek, contracted with six South Side blocks for the current winter, doubling that number from a year prior. He relies on word-of-mouth advertising, not traditional methods such as print, radio or television ads. “I give them a flat rate, and they divide it up among the houses,” he says. “Some people [in the block] pay, some don’t.”
Early on, Puskar – who took over outreach 11 years ago – and his block’s two other plow leaders vowed to not harass neighbors to sign up. “If you try shaming, it just pisses people off,” he says. “Nobody’s policing it.”
The Upper East Side is home to some of the city’s oldest neighborhoods, with the bricks in Puskar’s alley laid in 1909. Due to its rough surface and deep wheel ruts, “the city has told us this is one of the four or five worst alleys in the city to plow,” says Puskar. “We tell [our service] to be liberal with the salt. Otherwise, we get these crazy wheel ruts. A flat plow can only clear down to the highest point, leaving the ruts full. The snow in those low ruts gets packed down, melts, refreezes, and it ends up about as nice and smooth as the moon.”
On the other side of town in Bay View, Daniel Dickover coordinated his first year securing alley plow service for his block of South Herman Street and Clement Avenue. Before the snow flew, 20 of the 35 households along his alley had paid up, leaving him about $350 short of the $1,500 contract. He was still hitting up neighbors as the new year approached. “I would pay $200 [all season] for this,” he says. “When you’re slaving away for five hours removing snow, how much is it worth?”
Puskar doesn’t mind putting in the time each fall to recruit households’ fees. “It’s the law of the land,” he says. “We knew what we were getting into when we bought [our house].”

How Much Would It Cost the City?
DURING THE THREE WINTERS ending in spring 2018, Milwaukee’s Alley Plowing Pilot Study used front-end loaders to remove snow from the alleys of two neighborhoods, one near Capitol Drive and I-43, and another just south of Silver Spring Drive between 35th and 42nd streets. In an 11-page report to the Common Council, then-Commissioner of Public Works Ghassan Korban cited various challenges, including snow blocking the garage apron (the concrete slab in front of an overhead door) and limited space to deposit cleared snow. End-loaders were slow and expensive to operate, says the report, and a better alternative would be plows attached to pick-up trucks. “The cost estimate for a city alley snow plowing program is estimated to be an initial $4,618,367 and $3 [million] to $3.2 million annually thereafter,” reads the report. For comparison, the city budgeted $9.6 million for plowing and salting streets in 2021.