NewsMy Block


My Block: South 27th Street doubles as a business district and a neighborhood

“27th street’s the best street in the city."
Posted: 9:14 AM, Nov 22, 2022
Updated: 2022-11-22 20:23:57-05

MILWAUKEE — In Milwaukee, there's a neighborhood with barely any homes. Very few people live there. But the feeling of community is as strong as any cul-de-sac.

That neighborhood is called South 27th Street, and it's part of Historic Highway 41.

So how can a commercial district, on a busy road be considered a neighborhood? Because a neighborhood can be where you work too. After all, a neighborhood is what you make of it and the relationships you build with the people nearby.

“27th street’s the best street in the city," Jeff Majdoch who owns Big Putts on South 27th Street said.

“Every color. Every creed. Every religion. Every person you can possibly think of is in this neighborhood," Roberto Montemayor, the owner of Monterrey Market on South 27th Street said.

In this edition of the My Block series, I met with Roberto Montemayor and explored South 27th Street which is also known as Historic Highway 41. I wanted to learn about the neighborhood through his eyes and experiences. Where we went and who we talked to was all up to him. There was no script to follow. Welcome to South 27th Street.

Historic Highway 41

Historic Highway 41 runs all the way from the Upper Peninsula in Michigan down to Miami, Florida. It was constructed in 1926. Highway 41 was the main road drivers took to get between Chicago and Milwaukee until I-94 was built in the mid-1960s.

S. 27th Street
A picture of South 27th Street at Morgan Avenue taken in 1964.

The part of this long road we are examining for this story is between Oklahoma and College Avenue in Milwaukee. It's known as the South 27th Street Business Improvement District.

The neighborhood stretches from Oklahoma Avenue in the north and travels south to West College Avenue. It's roughly four miles of primarily commercial enterprises.

Roberto Montemayor & Monterrey Market

Roberto Montemayor, who is also known as Don Roberto, is the owner of Monterrey Market on South 27th Street. He also owns another location on South 13 Street too. It's a family-owned grocery store that has all types of foods and products but also carries tons of products for the Latino population that lives in the area.

1 Roberto .JPG
Roberto Montemayor is the owner of both Monterrey Market locations in Milwaukee.

"You have the ability to come into a grocery store and you’ll have those spices that you’ll be able to buy. The tomatillos. You’ll be able to buy the cilantro (and) the avocados. All that fun stuff, but, you know that you can also come here and if you’re going to have a party you're going to have a piñata as well," he said.

Roberto sees it as equally important to offer a variety of foods for all populations but also cater to the Latino demographic. They make their own homemade tortillas and have a mini taquría inside too.

As Roberto walks the isles of his grocery store, he talks to many of the people he sees - in Spanish and English.

"I know these people. I’ve known them before they were even born. Obviously, I've known some before they had children, and now they have children, and those same kids are now teenagers," he said.

His grocery store is a gathering place. It's one of the most popular businesses on the street because it's also one of the most important. It's where people come to get the ingredients for family dinners. It's the building block for family traditions.

"You do need to have that meal that - with mom, dad, and the children together," Roberto said.

Once we walked through the aisles, Roberto took us across the parking lot to his neighbor.

Ruby Hererra & Physical Therapy Milwaukee

Physical Therapy Milwaukee is directly across the parking lot from Monterrey Market. Dr. Sylvestra Ramirez owns the business and has opened three locations since 2013. She wasn't in the office when we visited. However, her employee Ruby, who knows Roberto well, was there.

“In my first grocery store, Ruby here was actually one of our first cashiers," Roberto said.

Ruby Hererra
Rub Hererra works at Physical Therapy Milwaukee and use to be an employee for Roberto Montemayor.

Ruby works at the front desk. She enjoys working at Physical Therapy Milwaukee. She feels like there is a strong sense of community among all the businesses. They know each other. They help each other out. South 27th Street is no different from any residential neighborhood. Everyone is close to each other. Plus, just as neighborhoods have community organizations, many of the businesses here are all part of the same communal group too.

“Just the fact that a lot of the businesses that are here are like either family-owned or have just been around so many years that people are very familiar with the area," Ruby said.

Beyond the physical services they offer, she is happy to be part of a bilingual business that can help people who sometimes aren't able to receive the care they need due to language barriers.

“There’s a lot of things that sometimes patients don’t understand, and having someone who speaks your own language, and is able to explain things to you is always a plus," she said.

S. 27th Street
A view of Historic Highway 41 near the corner of S. 27th Street and Howard Avenue.

South 27th Street is located on Milwaukee's southside and has a large Latino population which makes services like these so important. It's a similar philosophy to that of Monterrey Market. While both businesses can be visited by anyone, there is an emphasis on the Latino population. In fact, Physical Therapy has made it a point to open locations in Spanish-speaking areas.

"(Dr. Sylvestra Ramirez) wanted to be at a location where it's accessible to all patients. We currently just opened a second location at South Cesar Chavez," Ruby said.

After our tour of the Physical Therapy Milwaukee office, we hopped in Roberto's car and drove a mile down Historic Highway 41 to his friend's business Bigg Putts.

Jeff Majdoch & Big Putts

Bigg Putts is a miniature golf course and arcade. On the front of the building is a joke and nod to the song 'Baby Got Back' from Sir Mix-A-Lot. It reads 'I like Bigg Putts and I cannot lie'.

I like big putts
The front of the Big Putts, a miniature golf course and arcade.

Big Putts has been around since 2004 and is owned by brothers Jeff and John Majdoch. It has also experimented with offering laser tag and go-karts. These brothers are also the owners of the Halloween store by the State Fairgrounds. It's the giant Jack-o-lantern you can see from the highway.

Jeff said that his favorite part of the neighborhood is how diverse it is.

"People of every color, every race, every religion, and everyone gets along. It's kind of the best of every world right smack in the middle of Milwaukee," he said.

Jeff Majdoch
Jeff Majdoch is the co-owner of Bigg Putts with his brother.

While Jeff doesn't live in Milwaukee, he did say that South 27th Street is the best street in Milwaukee. He knows his neighbors like Roberto and he has tons of returning customers that are part of the Big Putts family.

"Having worked all over the city, this is the area that I call home."

Big Putts didn't just make a random decision with their mini golf course. They went with a 'wheel theme'. They have tons of vintage car parts and street signs that pay homage to Historic Highway 41. They also have skateboards and ramps that are a nod to the 'The Turf' skatepark that used to be nearby.

Bigg Putts
A look at the 18-hole mini golf course at Bigg Putts on S. 27th Street.

"We kind of tie everything - 27th street and the Southside - into our funny little world here."

After a few holes of mini golf and trying out some of the arcade games, it was time to head back to Monterrey Market to wrap up the tour of South 27th Street.

One Last Question

All My Block stories end in the same way. We return to the place we started, and I give the last word of the series to the tour guide. In this case, that was Roberto.

Before that, you can be part of the My Block series by reaching out to James Groh at or calling/texting him at (414) 254-8145. You can submit your neighborhood, yourself, or a neighbor for a feature.

"Is there anything else you’d like to say about your neighborhood?" I asked.

"I think what has really created this neighborhood, this community, is the fact that we are ultimately all united in one way or another," Roberto said.

Report a typo or error // Submit a news tip