Recently, I teamed up with Amtrak, Passion Passport, and friend/photographer Alina Tsvor for a weekend of adventure and exploration in Chicago’s neighbor to the north: Milwaukee. We hopped on the Hiawatha Line to Brew City on a Friday evening. Although the ride is under two hours, we listened to music, researched what to do in Milwaukee on the train’s wifi, snapped perspective shots down the aisle, and enjoyed the relaxation of watching the world go by that only trains can bring.

Amtrak Passengers Aboard Train

Arriving at Amtrak’s downtown station around sunset, we grabbed burgers and walked along the river back to the hotel to rest up for our day ahead. We wondered what the dim, shimmering reflections and boat silhouettes would look like in the morning.

After several enthusiastic recommendations on Instagram, Comet Café was our first stop Saturday morning. Our expectations only grew when we saw the groups of people outside cheerfully waiting to be seated. Sipping coffee from homey mugs, the time passed quickly until we were ushered inside, the atmosphere a cross between diner and bar lounge. The first bite of my Comet Benedict—homemade biscuit, smoked ham, fried egg, with hashbrowns (only $8)—quickly confirmed that the food was well-worth the wait. For the biscuit in particular, I consciously had to pace myself and close my eyes to savor every flaky, mealy note. And although we didn’t get to experience it, the restaurant hosts Bacon Night on Sundays.

With our bellies beyond satisfied, we made our way to the Mitchell Park Conservatory. Famed for its triplet domes, approaching the glass beacons was like walking up to Emerald City: a mix of fascination and curiosity at what you’ll find inside. Each structure transported us to a different climate and horticultural theme: Tropical, Desert, and Floral Show. We leisurely strolled through the flora—from ivied waterfalls to cacti—forgetting we were even in the Midwest.

Mitchell Park Horticultural Conservatory in Milwaukee

Garden Table and Chairs in Mitchell Horticultural Conservatory, Milwaukee 2

Couple Sitting on a Pier along the Milwaukee Riverwalk

Nothing highlights the summer charm of the city like the Milwaukee Riverwalk, lined with public art and families enjoying the breeze. People-watching, dangling our feet in the water, and gazing at boats passing by during the sunset (or sunrise for the morning people) was the perfect way to wind down. Although famished, we couldn’t resist stopping by a fake British telephone booth for some snaps. If you’re feeling active, you can rent kayaks and dock for a bite or a brew in the numerous pier-side cafes, restaurants, and pubs. After a sushi dinner at Sake Tumi, we strolled around admiring the downtown architecture (my favorite of which was the Mitchell Building National Register of Historic Places) in the waning light of dusk before returning to the hotel.

We hurried through brunch at Wolf Peach—a brunch spot which offered playfully-named dishes like the ‘I’ll Have What She’s Having’—to make the most of our Sunday before leaving. We had an early afternoon departure and wanted to have plenty of time for one of the city’s star attractions.

Calatrava Milwaukee Art Museum


Calatrava Quadracci Pavilion in Milwaukee Art Museum

No visit to Milwaukee is complete without a visit to the Milwaukee Art Museum. Even before entering, the MAM opens your eyes with its bridge and wide, white ‘wings’ (reminiscent of sails) contrasted sharply against the blue sky. The interior is just as magnificent as you are greeted by the famous Quadracci Pavilion (designed by Spanish architect Santiago Calatrava) upon entering. You are drawn to the latticed windows overlooking out onto Lake Michigan; it’s almost as if you’re at the helm of a giant, white spaceship. Only once your eyes adjust to the pristine, glaring white do you manage to pull yourself away to discover the rest of the Museum’s gems of geometric hallways to its 30,000 works of art including the current exhibit Van Gogh to Pollock: Modern Rebels. With not nearly enough time there, we had to be mindful to not lost ourselves too heavily in the art and architecture so we could make it back to the train.

Across the street from the Downtown Milwaukee Amtrak Station is Stone Creek Coffee Roasters, a homey and friendly place to grab a delicious scone and brew if you have some time to spare before catching your train.

After a brief but fun-filled 48 hours, boarding the return train home was bittersweet. We hunkered down in our seats to catch up on emails and grin about memories made over the weekend. We made sure to walk through Chicago Union Station’s grandiose Great Hall as our final stop before returning to real life.

Amtrak Union Station Great Hall with American Flag in Chicago by Alina Tsvor

For me, the most pleasantly surprising discovery of the weekend was the chameleon diversity of Milwaukee. There you can span the spectrum from Midwest charm along the river to Parisian refinery in classical architecture to spaceship modernism in the ethereal vision of Calatrava, all in the span of a few blocks. As a Chicagoan, it’s easy to overlook other cities in the Midwest, but in doing so you miss out on a lot. Milwaukee is an easy, enjoyable escape from the Windy City and only a train ride away.


Words by: Elliot Vernon; Images by: Alina Tsvor and Elliot Vernon

Elliot and Alina visited Milwaukee through a collaboration between Amtrak and Passion Passport. All opinions are their own.