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These Are The 3 Underrated U.S. Cities Which Surprised Me The Most

Alex Johnson

Alex Johnson

August 12, 2026 · 6 min read

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These Are The 3 Underrated U.S. Cities Which Surprised Me The Most
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I’m lucky enough to have travelled the length and breadth of the United States. Along the way, I’ve seen the good, the bad and the ugly, though mostly the former. Of course, like most British travellers, my first visits to the U.S. were focused on ticking off those bbig-namedestinations.

trees and a lake on boston common boston usa
My first trip to the U.S. took me to Boston. It feels like a lifetime ago now (Credit: Alex Johnson)

But once I’d done New York (can you evertruly “do” New York?), Boston and LA, I decided I hadn’t seen enough. So, I set about working my way around those cities which fly under the tourist radar. These are the three which surprised me most, and all of them in a good way.

1. Milwaukee

I’ll be straight from the outset: I am in love with Milwaukee. I’d wanted to visit ever since first watching Love Actually, in which Colin Frissell leaves London for Milwaukee in search of love. Love, he found, and to an extent, so did I, albeit the kind a traveller reserves for those special few destinations.

a snowy scene in a park in milwaukee wisconsin usa
Milwaukee looks even better under a blanket of snow (Credit: Alex Johnson)

I arrived in Wisconsin’s largest city on a snowy winter’s afternoon. First impressions count for a lot, and The Brewhouse Inn & Suites made a lasting one. If ever you need a hotel in Milwaukee, make it the Brewhouse.

Of all that Milwaukee is famous for, beer is generally top of the list. Over the years, the city has given us Miller Lite, Pabst Blue Ribbon and dozens more hoppy delights. To this day, Molson Coors have their head office here. They alone produce 1.2 million barrels in Milwaukee every year.

original pabst blue ribbon production facilities at the brewhouse inn and suites hotel in milwaukee wisconsin usa
The Brewhouse occupies the former Pabst brewery (Credit: Alex Johnson)

I paid a visit to Pabst Mansion, the former home of Capt. Frederick Pabst, who founded the brewery, was before grabbing dinner at the hotel’s restaurant. Iapologizee to anyone from Chicago, but Milwaukee’s tavern-style pizza is in another league entirely.

a tavern style pizza topped with sausage, mushrooms and garlic aioli at on tap restaurant in milwaukee wisconsin usa
I can still taste that garlic aioli (Credit: Alex Johnson)

My evening in Milwaukee was one of the best anywhere in the U.S. The Milwaukee Press Club might just be one of the best, and certainly most unique, bars in the country. The walls are adorned with signatures of the makers and shakers who’ve graced it. Plus, the barman makes amazing cocktails.

signatures and presidential seal on a wall at milwaukee press club a bar in milwaukee wisconsin usa
The Press Club is open to all (Credit: Alex Johnson)

After a night of bar hopping- Deer Camp and Drink Wisconsinbly were my favourite spots- I spent the next morning learning all about Milwaukee’s other famous export. Harley-Davidson motorcycles have been manufactured here since the very beginning, and their museum and visitor centre is well worth a visit.

Sadly, Minneapolis was calling, so I hit the road and bade farewell to Milwaukee far too soon. I’ll be back, and you should go to.

2. Detroit

We’ve all heard about Detroit, and generally for all the wrong reasons. The home of the U.S. automotive industry went through a very rough patch towards the end of the 20th century. Unemployment skyrocketed, as did poverty, and the city became rife with crime.

the skyline of detroit michigan usa at night
Detroit has grown to become a financial hub (Credit: Alex Johnson)

I’m glad to say, those days are over. Detroit has rebuilt and is back stronger than ever. Michigan’s largest city is somewhere you really should consider visiting.

I arrived late on a Flixbus from Toronto in need of some form of excitement. The drive through Ontario has to be one of the most boring I’ve encountered. I checked into a massive corner room at a Wyndham overlooking the Detroit River before setting off to a rooftop bar.

michigan central station a restored railroad terminus in detroit michigan usa
Michigan Central Station spent decades lying in rack and ruin before being redeveloped between 2018 & 2024 (Credit: Alex Johnson)

It was at the Motor Bar in the old Cadillac Building that I met a very interesting insurance broker who was only too keen to show me his favourite haunts. Another fun evening followed, and he left me with plenty of tips for the following day. Top of his list was to visit Michigan Central Station , which has recently undergone a $740-million facelift.

But before that, there was one place which has been on my bucket list for years: the Henry Ford Museum of American Innovation. Safe to say, I’m extremely glad I was finally able to visit. There’s far more here than Ford cars; planes, trains and automobiles from every decade are on display. You could quite easily spend a whole day at the museum.

the bus on which rosa parks kicked off a civil rights movement in montgomery alabama on display at the henry ford museum of american innovation in detroit michigan
The original bus on which Rosa Parks refused to move seats for a white person is the star of the show (Credit: Alex Johnson)

I’ve often stolen a saying from Aldous Huxley. It goes “to travel is to discover that everyone else is wrong about other countries”. This is oh-so-true of Detroit, albeit a city, and I highly recommend you give Motor City a chance to prove everything you’ve heard is wrong.

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3. Cheyenne, WY

I had no plans whatsoever to visit Cheyenne. To all intents and purposes, my time in Wyoming was meant to be spent in Sheridan. A winter storm put pay to that idea, and I found myself with a night in Cheyenne instead.

a skywest airlines united express bombardier crj200 at cheyenne airport wyoming usa in snow
The pilots did an amazing job in getting us to Cheyenne despite the weather (Credit: Alex Johnson)

The snow had put pay to any chance of getting a rideshare from the airport, but some locals kindly phoned a friend to give me a lift to the Historic Plains Hotel. The less said of the hotel, the better. I’m sure it was once a grand place to stay, but time hasn’t treated it well.

I spent the following day exploring Wyoming’s tiny capital, population 65,132, a figure the kindly gentleman who drove me from the airport knew off by heart. I headed first to a fantastic railway museum. Cheyenne sees no passenger service, though it is an important freight depot as BNSF and Union Pacific meet here.

a model railway at cheyenne depot museum wyoming usa
The upstairs of the museum is given over to an elaborate model railway. The curator was so enthusiastic, I thought he’d never let me leave (Credit: Alex Johnson)

Train-fix completed, I spent a couple of hours wandering around through the snow-covered streets. There isn’t all that much to do in Cheyenne, but it’s a wonderful city for aimless strolls, especially under a blanket of snow.

I thoroughly enjoyed my unexpected stopover in Cheyenne. One of the wonderful things about travel is encountering the unplanned. Sometimes it pays off, sometimes you find yourself stuck somewhere you really don’t want to be. On this occasion, Cheyenne didn’t disappoint, and I had no regrets ending up there.

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Alex Johnson

Alex Johnson

I've always loved travel. All the little annoyances: the rigmarole of airports, the missed connections, the breakdowns, the missing reservations, are not annoyances to me. They're what I live for. Travel, I think, is best measured in experiences, not distance. It’s the people you meet, the unexpected encounters, the weird, and the wonderful of this world that makes every journey special. Sometimes, a short hop on the train to a new town can be just as rewarding as a first-class flight across the Atlantic. My favourite destinations are those less visited, which led me to writing my first book, A Long Weekend in Ulaanbaatar. My second book, Running the Milk, focuses on another of my passions: air travel.

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