The Ultimate Weekend in Milwaukee

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You don’t have to be a car fanatic to automatically associate Ford with Detroit, or Dagenham if you’re British. The same should apply to motorcycles. I know little about them and have even less desire to change that. I mounted a stationery bike once and promptly fell off, vowing never to go near one again. But even I know what a Harley-Davidson is; what I didn’t know is that they came from Milwaukee.

And that’s the thing about Milwaukee. We all know it exists, but very few know what it’s about and even fewer will ever visit. Truth be told, my only prerequisites for the city were based entirely on one scene in Love Actually.

Within five minutes of arriving in Wisconsin’s largest city, I’d fallen in love. Under-the-radar Milwaukee is truly special. Quiet, yet not boring, safe and friendly, Milwaukee is full of character. Welcoming locals who always have time for a chat give the 31st most populous city in the U.S. a small town feel, the glorious architecture transports you to a bygone era and the endless list of things to do makes you never want to leave. You may not have considered a weekend in Milwaukee, but you really should.

Getting to Milwaukee

By Air

Milwaukee Mitchell International Airport (MKE) is located less than six miles from Downtown with a regular bus service connecting the two. It’s served mainly by domestic flights along with a handful of seasonal services from Mexico.

If you’re traveling from outside the U.S., flying to Milwaukee will often involve a transfer. If you don’t fancy that, Chicago O’Hare International (ORD) is the nearest international hub. Just over an hour’s drive from Milwaukee, and well connected by public transport, flying into Chicago gives you the option of exploring the Windy City ahead of your weekend in Milwaukee.

By Land

If you haven’t rented a car, the good news is, it’s easy to reach Milwaukee by public transport. Amtrak provide a frequent service between Chicago and Milwaukee with up to 7 departures per day. The journey takes around ninety minutes. Alternatively, regular intercity buses link Milwaukee with Chicago (2 hours) and Minneapolis (7 hours).

When to visit Milwaukee

The best time to visit Milwaukee is whenever you can; there really is no bad time. Milwaukee’s climate is very similar to Chicago’s: the winters are cold with frequent snowfall whilst summers are hot and humid.

Visiting in winter allows you to take advantage of lower hotel prices. What’s more, Milwaukee looks even more beautiful under a blanket of snow. If you prefer not to have to layer up, June to August are the best months to explore Milwaukee with temperatures hovering around 20°C (70°F).

Where to stay for a Weekend in Milwaukee

There’s plenty of reasons a weekend in Milwaukee is always a good idea, but if you need another one, the choice of independent boutique hotels is it. Better still, even the very best hotels in Milwaukee offer excellent value, especially if you’re arriving after a few nights in Chicago.

Without doubt the ultimate base for this ultimate weekend in Milwaukee is The Brewhouse Inn and Suites. Housed in the original Pabst Blue Ribbon brewery, The Brewhouse is a beer lover’s dream. Complete with original fermentation tanks, the suites are beyond spacious and come with all the mod cons you wouldn’t expect from a 175-year old building. Of course, you have to sample a pint of Blue Ribbon in their bar and their classic Wisconsin tavern style pizza goes down a treat.

If you’re looking for a hotel in the heart of Downtown, look no further than Kinn Guesthouse. This upscale boutique has just 31 rooms along with a rooftop with panoramic views and an excellent brunch restaurant.

Another gem for beer lovers, The Pfister is one of the most luxurious venues for your weekend in Milwaukee. A short walk from the city’s top shopping and dining destinations, this beautiful spa hotel is steeped in history. Opened in 1893, in the days when the Mid West marked the western extreme of the U.S., the hotel was dubbed the “grandest hotel in the west”.

Itinerary for the Ultimate Weekend in Milwaukee

Day 1

Morning: Arrive and Settle In

Downtown Milwaukee is very walkable. Once you’ve dropped your bags, spend the morning getting your bearings and admiring the beautiful Victorian buildings and strolling along the banks of the Milwaukee River. Stop off for coffee at the Cafe at the Pfister. Their café and barista station are open daily for both residents and non-residents.

A great way to get to grips with any new city is to take a sightseeing bus tour. This two-hour tour departs from City Hall and passes the historic Pabst Theater, Black Cat Alley and North Point Lighthouse.

Afternoon: History & Beer

Head to the Milwaukee County Historical Society to learn about the city’s history. Home to Native Americans for thousands of years, European settlers arrived in Milwaukee in the mid-18th century. In 1846, the city of Milwaukee was founded by Solomon Juneau, Byron Kilbourn and George Walker.

The Historical Society’s permanent exhibits tell the story of the city’s founding and growth to a regional powerhouse. There areregularly changing temporary exhibitions too. The highlight for 2025 is Brew City which tells the story of brewing in Milwaukee.

If there’s one thing Milwaukee is more famous for than anything else, it’s beer. Frederick Pabst moved to Milwaukee from his native Germany in 1848. Whilst employed as a ship’s captain, Pabst became friends with brewery owner Phillip Best. When, in 1863, Pabst ran his boat aground in Milwaukee harbour, he set about looking for a new career and, the next year, purchased a 50% stake in Best’s brewery.

In 1892, Frederick Pabst built Pabst Mansion where he would live with his family until his death in 1904. Now on the National Register of Historic Places, the mansion has been fully restored and guided tours are offered five days a week. It’s best to book your tour in advance.

It’s not just Pabst Blue Ribbon which is synonymous with Milwaukee. Miller was founded here in 1855, their iconic Miller Lite lager being brewed here to this day. Now part of the multinational Molson-Coors group, whereas many breweries have shifted production to cheaper locations, the Miller brewery’s production has increased with Coor Light now being brewed in Milwaukee.

Make the Miller Brewery the next beer-themed stop of your weekend in Milwaukee. Their guided tours offer a fun insight into the brewing process and you get to delve into a nother piece of Milwaukee history along the way. Better still, there’s no shortage of free samples along the way.

Evening: Theaters and More Beer

Head to On Tap at the Brewhouse Inn and Suites for a classic Wisconsin dinner. Their traditional tavern-style pizzas are divine and the fish fry could almost rival British fish and chips. Of course, there’s only one fitting drink to accompany dinner: a pint of Blue Ribbon. It was brewed in this building right up until 1996.

Continuing this weekend in Milwaukee, head downtown to catch a show at the Pabst Theater. Purchased by Frederick Pabst in 1890, the building was originally an Opera House. When it burnt down in 1893, Pabst had it rebuilt and it reopened two years later as the Pabst Theater. Today, it hosts plays, musicals, concerts and comedy with events on every day; check the calendar and book tickets in advance.

After the show, cross the road to the Newsroom Pub, Milwaukee’s quirkest bar. Serving as the headquarters of The Milwaukee Press Club, a fraternal organization for members of the press community from across Wisconsin, the walls are lined with signatures from authors, journalists and politicians who have graced the club since its inception in 1885.

If you’re not quite ready to turn in for the night, cross the river to North Dr MLK Jr Drive, Milwaukee’s nightlife hotspot. There are dozens of bars, beer halls and night clubs dotted along the street.

For something a little out of the ordinary, check out Deer Camp where the walls are lined with taxidermy and when the night gets old, Drink Wisconsibly is a long time favorite drawing a younger crowd.

Day 2

Morning: Milwaukee on Two Wheels

Kick off the second day of your weekend in Milwaukee with a hearty breakfast at Brunch It Up. They serve all the brunch classics from eggs and bacon to chicken and waffles and benedicts. For the sweeter tooth, their croissant beignets and smores pancakes are the perfect sugary start to the day.

Ready for a day of exploring, cross the Menomonee River to visit Milwaukee’s top attraction. The Harley-Davidson Museum tells the story of this iconic brand from its founding to the present day. See the very first Harley built and walk through time to see how their motorcycles have developed through the years.

The museum also hosts a factory outlet and the Harley-Davidson shop where you can purchase everything from memorobillia to your own bike. The Motor Bar & Restaurant is ideal for a quick lunch.

Afternoon: Art & Culture

The next stop on our weekend in Milwaukee is nothing if not niche. The National Bobblehead Hall of Fame is one of those places you have to go purely becuase it’s so unusual. Home to over 10,000 bobbleheads, the collection was started by two friends in 2004. By 2019, they had amassed so many, they decided to open a museum.

Heading back across the river to Downtown, pay a visit to the Grohmann Museum. Slightly more conventional, but by no means less interesting, the museum is home to the world’s largest collection of art depicting the evolution of human work. Over 1,900 paintings and sculptures show the evolution of the working human.

Evening: A Taste of Germany

Round off your weekend in Milwaukee with an evening of authentic German cuisine at Mader’s Restaurant. Set in a stunning Bavarian-style lodge, Mader’s is decked out with grand chandeliers and a $3 million collection of art. The food is just as impressive.

Expect all the German favorites from giant pretzels and wurst to saurerbraten (roast beef) and schnitzels. Their signature German sampler platter is perfect when you can’t decide. It comes with Weiner schnitzel, sauerbraten, rippchen (pork chops) and potato dumplings.

For a fitting end to the evening, head to the Old German Beer Hall, a must for every weekend in Milwaukee. An ode to the German migrants who made brewing big business in Milwaukee, their draft list is impressive.

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