Walking Chicago’s Beer Baron Row: A Journey Through Wicker Park’s Liquid History

When I travel, I seek out tours that go deeper than the postcard version of a city. On a recent trip to Chicago with my daughter and her friend, I connected with Henry from Portal Tours, someone who had once joined one of my Buenos Aires food tours. He designed a custom Chicago walking tour for us through Beer Baron Row Chicago in Wicker Park, focused on the city’s long, complex relationship with alcohol. It turned out to be the most memorable afternoon of our trip.

Exploring Beer Baron Row Chicago: Mansions of the Brewing Elite

We began on Hoyne Avenue, better known as Beer Baron Row Chicago. In the late 1800s, German immigrant brewers built lavish homes here, their fortunes from lager and tied-houses etched into turrets, stone trim, and sprawling gardens. Henry stopped at several of these mansions, sharing stories of the families who helped shape Chicago’s beer culture.

One of the grand mansions on Beer Baron Row Chicago, built by German brewing magnates in the late 18

Another historic home on Beer Baron Row Chicago, showcasing bay windows, stone trim, and lush garden

Wicker Park Walking Tour on the 606 Trail

Our path crossed The 606, the elevated greenway built on a former rail line. This 2.7-mile park connects neighborhoods like Logan Square, Humboldt Park, Bucktown, and Wicker Park. Henry explained the city is exploring plans to extend it toward the lakefront — proof of how Chicago continually reinvents its urban spaces.

Crossing the 606, Chicago’s elevated trail built on a former rail line. This 2.7-mile path links Wicker Park with nearby neighborhoods, blending green space, public art, and city views.

Schlitz Tied-Houses and Chicago’s Beer History

Next came a highlight: a former Schlitz tied-house, built in 1898 and restored with its colorful “belted globe” emblem. These brewery-owned taverns sold only Schlitz beer, part of a strategy that reshaped Chicago’s drinking landscape. Ironically, many tied-houses were a response to temperance efforts to restrict alcohol — efforts that ended up making beer cheaper and more widespread.

We later passed another tied-house, painted entirely white, its emblem erased. The contrast between preservation and erasure was striking, a reminder of how fragile local history can be.

A restored Schlitz tied-house in Chicago, built in 1898 and marked with the brewery’s colorful belte

Close-up of the Schlitz belted globe emblem, a symbol that once marked brewery-owned taverns across

A former Schlitz tied-house painted entirely white, even covering its belted globe emblem. A stark c

The Map Room and the Chicago Handshake (Malört + Old Style)

Our walk took us to The Map Room, a bar I remembered from my Chicago days. Opened in 1992 as a “traveler’s tavern,” its walls are still lined with maps and vintage guides. Here Henry treated us to the legendary Chicago Handshake: a shot of Malört with an Old Style chaser.

The “Chicago Handshake” — a shot of Malört with an Old Style chaser. A bitter-sweet local tradition that every visitor has to try at least once.

Malört’s reputation as “the bitterest drink in the city” precedes it. Personally, I didn’t find it unbearable, like Sol in the video below — maybe our palates are already trained by Fernet — but the lingering aftertaste was unforgettable. And in a place like The Map Room, it felt right at home.

First taste of Malört! My daughter coughed and swore it off immediately, while her friend Sol compared it to Campari and said it wasn’t that bad — the perfect snapshot of Chicago’s most infamous drink.

Quirks, Cannons, and Wicker Park Oddities

Wicker Park is full of surprises. We spotted quirky yard displays, Cubs flags mixed with animal figures, and even a mansion with a WWI-era howitzer cannon in its yard. Built in 1878, the home later became an American Legion Post, and the cannon has stood there since 1934. Only in Chicago do you find a beer baron mansion with artillery on the lawn.

The Sommers/Plautz House on Beer Baron Row Chicago, built in 1878 and later used as an American Legion Hall. Its red brick design and unusual cannon on the lawn make it one of Wicker Park’s most distinctive mansions.

A Taste of History: Cohasset Punch, Chicago’s Forgotten Cocktail

Back at the park where we started, Henry had one last surprise: a taste of Cohasset Punch. First bottled in 1899, this fortified wine-style liqueur was once called “the definitive Chicago cocktail.” Sweet, bold, and port-like, it was the perfect closing toast to a tour that balanced architecture, immigration, prohibition, and culture.

Close-up of Cohasset Punch, a historic Chicago liqueur first bottled in 1899. Sweet and port-like, it was once called “the definitive Chicago cocktail.

Why Beer Baron Row Chicago Belongs on Your Itinerary

What made this tour special wasn’t just the places — it was the stories. Henry connected the dots between German immigrants, tied-houses, Prohibition, Malört, and forgotten classics like Cohasset Punch. It was Chicago told through its drinks and its bricks, its resilience and its quirks.

Henry from Portal Tours shares a final surprise in Wicker Park — Cohasset Punch, a forgotten Chicago classic, enjoyed right on the grass.

If you’re planning a trip to Chicago and want more than the usual Loop or lakefront highlights, I highly recommend Portal Tours. You can stroll through Beer Baron Row Chicago or come up with some custom itinerary of your preference. Henry knows how to bring history alive one mansion, one pint, and yes, even one shot of Malört at a time.