
(Photo compliments of Milwaukee Art Museum)
Many Chicagoans may not even realize there is a sizeable attractive, action-filled metropolis a mere 90 miles north of the loop that makes Milwaukee a perfect destination for a one-night stay or daytrip.
On a whim, after planning and hosting a gathering for over 60 friends and family the previous weekend we decided to escape Chicago on the 4th of July to spend a night in Milwaukee.
Finding where to stay
To begin our brief adventure, I chose to spin the proverbial wheel using “express deals” at Priceline.com to determine where to stay. The site indicated about six 4-star hotels downtown that all sounded fine to me.
We drew the Hilton on Wisconsin Avenue across from the convention center. This was the former Marc Plaza a period hotel built in 1928 that has been very well maintained and reminiscent of the Conrad Hilton, the brand’s flagship Chicago hotel though considerably smaller.
Our room on the 16th floor with one King bed was very clean, large and luxuriously appointed with contemporary furnishings including a recently renovated bath. In spite of the location next to the elevator it was very quiet. There was a minibar and a big screen TV that greeted us with a personalized welcome message.
The ample hotel lobby has a charming early 20th Century vintage vibe with very high ceilings and wood trim with gold accents. Also, there are three restaurants on the property and room service is available.
Our discounted price was just under $150 for the night including taxes and fees, easily 1/3 lower than any of the other posted rates for the same hotel online. I got another $15 rebate using my Capital One card.
Once we arrived, I learned that parking was an additional $40 per night with in-and-out privileges. I decided to check my Spot Hero app and noticed there were several nearby options at half the price. However, since it was Saturday night and metered parking was free all day Sunday I was able to park on the street across from the hotel for free.
We checked in after 4PM then took a ride through downtown and around the east side of the city, which like Chicago is the lakeside. This is really a great get-a-way location and ideal for those looking for a big city experience that is not on the hectic level or scale of Chicago.
Beginning with an architectural adventure
Driving east from the hotel on Wisconsin Avenue I was struck by how much of the 1880’s era architecture this city has retained. Chicago has eradicated most of the enormous terracotta clad brick “skyscrapers” that defined the growing urban centers of the late 19th and early 20th century.
In this case, the Federal Building & Courthouse (1892-99) with its large stone columns; the Iron Block Building (1860) with its cast iron facade; the Pfister Hotel (1893) is the picture of Gilded Age Luxury and the Chamber of Commerce Building (1879-90) on Broadway, features an impressive façade of carved ornamentation.
There are numerous additional architectural gems spanning over 150 years to find and explore from Buckminster Fuller’s geodesic domes (1967), Frank Lloyd Wright’s Burnham Block (1912-16) to The Calatrava “Wings” (2001) part of the Milwaukee Art Museum — a movable sunscreen that opens and closes like a giant bird and is one of the most recognizable architectural features in the world.
Fireworks on the lakefront
We headed north along Lake Drive in search of some 4th of July fireworks and settled in Atwater Park just past Capitol Drive in the adjacent suburb of Shorewood. It is the equivalent of Evanston in Chicago in terms of proximity to the northern boundary of the city.
The park features a dramatic bluff about 70 feet high overlooking Lake Michigan and has a dramatic switchback path down to the beach that is enjoyable during any visit.
Luckily, I keep a couple of foldable camp chairs in my trunk which we grabbed and walked about two blocks from Edgewood Avenue and Lake Drive.
Edgewood Avenue has a number of impressive mostly single-family homes built between 1915 and 1935 that are a mix of Tudor Revival, Colonial Revival, and Mediterranean‑influenced architecture on sizeable lots that range in price between $1 million to over $2 million.
We situated ourselves comfortably near the entrance of the park next to an illuminated public art installation of a seated human figure made of interlocking alphabetic characters forming a hollow, mesh‑like body by Jaume Plensa called Spillover Il.
Since the fireworks were being launched from the beach below, we were easily half way to where they ultimately exploded providing us an intimate immersive experience.
By the way, this is a nice drive and a spectacular view even when there are not fireworks to enjoy.
Afterwards we made our way back to the hotel to enjoy a cocktail and split an order of BBQ pulled pork sliders for a perfect late-night snack at the Miller Time Pub & Grill in the lobby.
Sunday Day Tripping
Now this is where things get a bit more interesting for day-trippers as the rest of this article is about how we spent a random Sunday in Milwaukee without really planning ahead.
We got kind of a late start because we just are not “crack-of-dawn” people which is one of the reasons we chose to stay the night. So, we were in search of Sunday brunch rather than breakfast.
Day tripping this will show that you can take a couple of hours to get up to Milwaukee on a Sunday and still have a nice full day experience. By the way if you choose not to drive, Amtrak has two Sunday morning trains that get in at 10:00 AM and 12:45 PM near the Hilton (check current schedules of course). Then getting around the city is quite easy by foot and/or via rental bike, scooter, bus and or a free tram.
In search of Sunday brunch
We first looked at the 3rd Street Market Hall on Wisconsin Avenue purported to be the second-best food court in the country according to USA Today. Featuring 20+ food vendors and a unique self-serve beer tap wall, it’s modern and family friendly though a bit more meat and drink forward then we were hoping for.
We also wanted to be outside. With no plan in mind, we headed on foot a few blocks north on Dr. Martin Luther King Jr. Drive to the 3rd Street Historical District.
This is a roughly a one block stretch of quaint old Italianate storefronts with a German vibe leftover from when this was the core of the German-American commercial area of the 1860s and early 1900s. Anchors on the street are the iconic Mader’s Restaurant and the Usinger Sausage Headquarters with the Pabst Brewery Complex nearby.
The three or four pubs on the street are more geared to beer and sausage than Sunday brunch but we landed outside the “Old German Beer Hall” whose chalkboard outside said “Sunday Brunch” including Chicken Schnitzel & Waffles ($14) and Bavarian Skillet ($14). We got one of each.
Surprisingly, they did not have coffee. So after we ordered I walked back a block to Starbucks in the Hyatt for a couple of Ventes.
The outside is long tables and benches and inside is classic old school German Hofbrau. This would surely to be a great place to watch a game or hangout with a group of friends. Food here is an afterthought and I give it a solid five out of ten but it was an overall pleasant experience. If you’re looking for sausage and beer you will do well in this area. If you’re looking for a brunch experience do a little more research and plan ahead.
A waterfront boat ride
We thought we would enjoy the Milwaukee Art Museum which alone is well worth the trip. But since it was nice summer weather and we were near the river we decided to do a river excursion which was the highlight of the day. We’ll save the museum for another trip in the fall or winter.
We opted for the mimosa Sunday Funday excursion on the Harbor Lady rather than the narrated historic tour on the Edelweiss. I think either (about $30 for 1.5 hours) would be fine but I was not in the mood for taking in a lot of information and instead just wanted to enjoy the sights. Tickets are available online at edelweissboats.com or at their ticket office on Highland at the river. By the way the riverwalk is a nice place for a stroll either before or afterwards.
The excursion from the landing along the river and out to the harbor was delightful. Great architecture along the way. A view of several bascule and lift bridges as well as an opportunity to view the activity along the shore and in the water including kayaks, sailboats, motor craft and other excursion boats.
Some highlights of the trip included viewing the Daniel Hoan Bridge from the lake with its bright yellow arch design that soars almost 120 feet above the water terminating on the north end near the Summerfest grounds.
We also passed the stunning Milwaukee Art Museum and got a glimpse of the Historic Third Ward which was our next destination.
The Historic Third Ward
By this time, you might gather I enjoy vintage architecture and Milwaukee has it in spades. Many years ago when were first married we lived here for three years and none of this was developed. The 3rd Ward area at that time was just a collection of mostly derelict light industrial and manufacturing buildings.
Now it is a very hip neighborhood of small businesses, trendy condos and a variety of neighborhood bars and restaurants along the river with the focal point being the Milwaukee Public Market reminiscent of Pike Place Market in Seattle with a large contingent of both prepared food and grocery vendors as well as of course plenty of beer options. We were looking for something light and opted for a couple of delicious tacos and lemonade at a bar near the front door.
A free ride
After exiting the market we spotted the Milwaukee Hop, a modern streetcar that uses both a pantograph (overhead electric lines) and its own battery power for certain segments. What caught my eye was the sign in the window that said, Free Rides. We thought, “what the heck” and got on, not knowing where it went.
As it turned out it was a very pleasurable easy tour of the city that passed by some of the places and buildings we had seen and many we had not. This is another great way to do some significant building and people watching. If you are inclined you can get off and explore then continue on to the end of the line (like we did) or grab another trolly back to where you began.
As it was, we logged about 4 miles of walking by the end of the day, so I did not mind doing a little riding as well by boat and trolly.
Meeting people
I don’t know if Milwaukee is any more friendly than anyplace else but we had a few enjoyable encounters. All of the waitstaff we interacted with were particularly nice and accommodating. At the fireworks we met a retired couple from Michigan now living in Milwaukee who told us about using the ferry from Milwaukee to Michigan to visit her elderly father. Sounds like a possible future trip idea.
On the boat we chatted with a nice fellow visiting from Sheboygan for the day and on the trolly we had a nice conversation with a young couple living in Milwaukee who were on their way to meet friends at the Public Market.
On the way home
No trip to Milwaukee is complete for us without a stop on the way out of town at Leon’s Frozen Custard on Layton on the south side. Established in 1947 this is not retro it is the real deal. A massive neon emblazoned frozen custard stand featuring outstanding frozen custard offered in a spectacular vintage drive-up only edifice.
One last tradition is an obligatory visit to the Mars Cheese Castle outside Racine on I94. If you forgot to pick-up some beer or cheese in Milwaukee this is you last chance to make your purchase with authentic Wisconsin hospitality. I have a friend that insists I bring him two or three loafs of cheese bread from their bakery and I’m fond of the giant elephant ear cookies which seem hard to find in Chicago.
This is hardly everything there is to do in Milwaukee – it’s not even a list of the best things to do, but hopefully it will inspire you to plan a day trip of your own when you just want to go someplace nearby for a short get-a-way.
Reno Lovison
(Reno Lovison is a Chicago video marketing professional and theater reviewer)





