November 2025
Why Milwaukee?
We have wanted to see Milwaukee for quite some time (we booked a trip several years ago and had to cancel) and we wanted to take the Amtrak, which departs from Union Station right across the street from our house. Thanksgiving seemed like a good time to travel by train.
This is a blog focused on hotels, so tell me a little about how you made your lodging selection for this trip. Were there lots of good choices?
If we don’t have a specific property in mind, we typically check a handful of sources to develop a short-list and then narrow down from there. Milwaukee isn’t a big enough destination to be covered on its own in most of our go-to sources, but just Googling “best hotels in Milwaukee” turned up a number of guides that we could then use to triangulate recommendations. We also typically check booking.com to see a property’s overall score and any trends with reviews; we did that for Milwauikee (even though we recommend — once a decision is made — to book directly with the hotel).
For this search, we pretty quickly arrived at a list of three hotels that met our criteria of (1) being centrally located, (2) having an on-site restaurant/bar (in case we couldn’t find a good option on Thanksgiving) and, (3) quite simply, looking interesting.
Why The Pfister?
The Pfister is Milwaukee’s historic “grand” hotel — it opened in 1893 — and, based on our research, it looked like a hub of activity for tourists and residents alike. We live a few blocks away from St. Paul’s classic, historic hotel — The St. Paul Hotel — and it always does a great job of celebrating the holidays. We imagined the same would be true for The Pfister. We weren’t wrong.
We arrived at The Pfister on a snowy Thanksgiving evening to find the lobby packed: folks heading to dinner at the hotel’s steak house, others enjoying a drink in the lobby bar, and some seemingly there just for the scene. As we checked in, staffers were putting the finishing touches on the lobby Christmas tree, which was a popular site for photos during our two-night stay. We also saw lots of preparation for traditional breakfasts with Santa that started the day after Thanksgiving.
Did The Pfister meet your expectations? If not, why not? What’s your assessment of the room given the price?
Our “premier king” room — in the tower (aka the round 1960s wing) — was perfectly comfortable. We technically had a view of Lake Michigan, but it was tucked behind other downtown buildings. One cool thing about the Pfister is its commitment to the arts. Not only does it house the largest Victorian art collection of any hotel in the world, the hotel also hosts an artist-in-residence program, and our room featured a print from one of the artists. We imagine that each guest room features a piece from a past artist-in-residence.
What else to say about the room? Its classic interior design aligned with the rest of the hotel, and everything seemed well-maintained. (A lovely person we met at a gallery during our stay noted that the hotel was in the process of renovating rooms; we think ours had been through a recent renovation.)
If we were to visit again, we might book a room in the original 1893 buildling. The historic side of the hotel is beautiful, and while the rooms might be smaller, we imagine they likely better align with the overall aesthetic of the hotel. (Our room in the round tower felt a little at odds with the hotel’s design.)
One of us forgot to sing the Bedbug Song. Do you regret this now?
I think, at this point, we can confidently say we’re in the clear, but the Bedbug Song can never hurt. You sing it at all hotels, even the fanciest, and the tradition has served us well.
“Bed bug, bed bug, leave me alone. Stay out of my bag; stay out of my home….”
What is one thing you will remember about the hotel?
How about two things?
First, the liveliness of the place. In addition to holiday events, the hotel hosted an Irish step dancing competition during our stay. Let’s just say, those dancers brought a lot of life — and a lot of luggage — to the hotel.
Second, the art collection was fun to see. We took time to wander the hallways and common areas, and it was like a visit to a museum. Milwaukee has a great art scene, which we didn’t expect, and The Pfister helps contribute to that.
It has been a long time since either one of us was in Milwaukee. How would you sum up your impressions of the city after this visit? Would you return?
We had only one full day in the city, but we made the most of it and ran out of time before we ran out of things to do. We would definitely return — maybe in the summer when we could more fully explore the area around Lake Michigan, the Riverwalk, and the Third Ward.
By the way, how was the Amtrak experience?
The ride down was great. It was Thanksgiving day, so we had a car practically to ourselves. The route is beautiful, and sipped a Bloody Mary while watching the scenery sweep past. On the way back, the train was fully booked, and we had to scramble to find seats, which weren’t together. The Borealis — the train between St. Paul and Chicago — doesn’t do reserved seats like the Empire Builder –the longer route — does. My guess is that lots of Borealis riders would be happy to pay a little more to get a reserved seat. We definitely would.
Even though the return trip started a little rocky, we arrived back in St. Paul to a snowy holiday evening with the European Christmas Market at the depot in full swing. It was pretty magical and awesome to get off the train and walk right across the street to our home.
Stay details:
- The Pfister Hotel, Milwaukee
- 2-night stay: November 27 and 28
- Premier King
What we did, where we ate:
- Dinner at Mason Street Grill
- Coffee at the Milwaukee Public Market
- Walking tour of the Riverwalk and the Third Ward
- Milwaukee Art Museum
- The Bradley Collection Exhibit — excellent!
- Drinks at Central Standard Distillery
- Dinner at La Dama
hotelling.org 