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How to Plan the Perfect Weekend Getaway in Milwaukee

How to Plan the Perfect Weekend Getaway in Milwaukee

Headed to Milwaukee for the weekend, for work, or maybe to catch a game? Well, stick around a little longer, and we’ll show you how to make the most of your time in Brew City.

There’s a lot more to do in Milwaukee than most give it credit for. To make planning your next trip even easier, we’ve put together this step-by-step guide on how to have the perfect three days in Milwaukee, and yes, there’s both beer and cheese involved.

How to use this guide to the perfect Milwaukee weekend or long weekend – This itinerary can be used in the order below, or feel free to mix and match to build your version of the perfect weekend here in Milwaukee. These are the things we do anytime we have friends or family come in from out of town! Have fun and enjoy our quirky but awesome little city!

Where To Stay for a Weekend in Milwaukee

If you’re looking for the best place to stay in Milwaukee, we suggest downtown Milwaukee hotels and over into the Third Ward. Some of the best restaurants in Milwaukee and a bunch of Milwaukee breweries are within walking distance.

There is always something going on downtown. If you’re traveling with friends or as a family, head over to Vrbo and see what homes/condos are available. Here are the best hotels in Milwaukee according to us.

Best Places to Stay in Milwaukee

Iron Horse Hotel Milwaukee (New & Trendy): One hundred years ago, the building was a warehouse. Now it’s an upscale hotel created for both bikers and business travelers alike. It has a warm, inviting atmosphere with a spectacular restaurant and modern feel that showcases art and events and is dog-friendly. Even if you’re not planning on staying, the Iron Horse is a truly Milwaukee experience that never fails to entertain. Address: 500 W. Florida St, Milwaukee – Check Rates 

Aloft Hotel Milwaukee (Great Location): It’s located near the Milwaukee Riverwalk, the Fiserv Forum & Deer District, and Old World Third Street. Aloft offers something for everyone, especially the food lover. Restaurants, brewpubs, boutiques, and so much more are steps from the door. Address: 1230 Old World Third Street, Milwaukee – Check Rates 

Pfister Hotel Milwaukee (Classic Milwaukee Hotel): Built in 1893, the Pfister has been a staple of Milwaukee Elegance for over 100 years. Everything in this hotel exudes a sense of class and style. Enjoy the night in beautiful rooms with impeccable service. The Pfister is a truly wonderful experience that harkens back to the glory of yesteryear. Address: 424 E. Wisconsin Ave, Milwaukee – Check Rates 

Milwaukee Airport Guide & Free Parking Code

Day 1 – Milwaukee Classics

Start your tour of Milwaukee with all the places and things that made the city what it is today. Your first day in Milwaukee will check off all the boxes, from beer to motorcycles to cheese.

Harley Davidson Museum - Things to do in Milwaukee

Harley-Davidson Museum

Another thing Milwaukee is known for, along with beer, is bikes, but not just any motorcycles, but Harley-Davidson Motorcycles. In 1903 William S. Harley and brothers Arthur and Walter Davidson set up shop here in Milwaukee, making their iconic motorcycles.

The Harley Davidson Museum is a collection of all things motorcycles and takes visitors through the entire history and evolution of the motorcycle. You don’t have to be a diehard biker guy to appreciate the museum. It’s a good way to spend part of your day with all types of visitors.

Lunch: Kopp’s Custard

You can’t say you’ve been to Milwaukee without eating a dish of frozen custard. You don’t even have to know what it is. Just know you need to find it when in Milwaukee. In our opinion (based on extensive sampling) one of the best places in Milwaukee to get Frozen Custard is Kopp’s Custard. Frozen custard or sometimes called Milwaukee Custard, is very similar to ice cream (but way better!).

The addition of a few more special ingredients makes for super smooth and rich ice cream like frozen custard. The flavors change every day with two special flavors in addition to vanilla and chocolate – check the flavor forecast here.

While you’re here, tick off a few more Milwaukee must-eats here, also like a delicious butter burger and deep-fried cheese curds. More than any other restaurant, this place and ones like it are the best representation of the food Milwaukeean’s love. It’s not fancy but just really good feel-good food. If you ask us, Kopp’s burgers are some of the best burgers in Milwaukee.

For a list of all the best Frozen Custard shops in Milwaukee, in case they don’t have your flavor while you are in town. There are 3 Kopps locations around the Milwaukee area:

  • 5373 N. Port Washington Rd. Glendale
  • 7631 W. Layton Ave. Greenfield
  • 18880 W. Bluemound Rd. Brookfield
Lakefront Brewery in Milwaukee - home to the best brewery tours

Miller Brewing Tour – Alternatively, Lakefront or MKE Brewing Tour

Milwaukee is the city that beer built. At one point in time, Milwaukee produced more beer than any other city in the world. Dubbed ‘Brew City’, Milwaukee was once home to several of the major beer brands in the United States.

Most of the big, old-time brands have shut their doors, but Miller Brewing still calls Milwaukee home, and you can take a tour through their extensive beer caves and sample three beers, and the best part – it’s free!

If you fancy a smaller craft brewery instead, then make your way to either Lakefront Brewery or MKE Brewing. Both of these local favorites put on a great tour with lots of samples.

Lakefront has been known as the best brewery tour in Milwaukee for many years, but MKE Brewing has really stepped up its game recently with great guides and lots of good beer samples.

You really can’t go wrong with either of these Milwaukee classics. If you happen to make a visit to Lakefront Brewery on a Friday, try and get a spot at the table for their famous fish fry.

In Milwaukee, Fridays are for fish fries, and Lakefront does one of the best in the city, with a full Polka Band and all!

Milwaukee Pabst Mansion

Pabst Mansion

Take a walk around the house that PBR built, which is a lot more classy than a can of the Blue Ribbon. Get a glimpse of life back into the rich and famous of Milwaukee’s early days at the Pabst Mansion.

This glorious estate was once home to one of the early beer barons of Milwaukee. There are several tours on offer every weekend, most of which include beer.

  • Address: 2000 W Wisconsin Ave, Milwaukee

Related Article: Things to do in Wisconsin Dells

Mader's Restaurant Milwaukee Building

Dinner at Mader’s

Get a taste of Milwaukee’s German heritage with a trip to Mader’s restaurant on Old World Third Street. Mader’s has been around since 1902 and is always on the top of the best restaurants in Milwaukee list. If you’re hungry, you can’t go wrong with the #1 selling dish, the pork shank.

  • Address: 1041 N Old World 3rd St, Milwaukee

Holler House

Finish off your day with a few frames at the oldest bowling alley in the world, yes – the world. I bet you didn’t know little ole’ Milwaukee, Wisconsin is home to the oldest commissioned bowling lanes anywhere.

They are so old the pins are still set by hand. Come for the nostalgia, stay for a few drinks. While in Milwaukee, make sure to sample the wide array of craft beers, and don’t miss the classic Wisconsin style Old Fashioned, made with brandy instead of Whiskey.

  • Address: 2042 W Lincoln Ave, Milwaukee

Weekend in Milwaukee City Skyline

Day 2 – Quirky Milwaukee

Breakfast/Brunch/Coffee: Comet Cafe

One of the most popular spots for brunch is Comet Cafe, located on the Eastside. This quirky Milwaukee cafe serves up one of the best brunches in Milwaukee. It doesn’t get quirkier than meatloaf omelet and bacon pancakes, but there is boring traditional stuff too.

They have extensive menu options for vegans & vegetarians as well. If breakfast isn’t your thing make sure to come for lunch or dinner. Their compact turkey dinner is to die for. Everything is made from scratch in-house.

  • Address: 1947 N Farwell Ave, Milwaukee

Cheese Head Factory

If there is anything you know about Wisconsin before visiting, it’s probably our very unique headgear that we wear to sporting events – The Cheese Head. The main season to wear such a cheese-inspired headdress is for the cooler months when the Green Bay Packers play, but the Cheesehead was actually invented here in Milwaukee.

Come see where it all started at Foamation Inc, in Milwaukee’s 5th ward neighborhood. Here you can take a tour of the factory and even make your own cheese head as part of a special tour.

  • Address: 1120 S Barclay St, Milwaukee

Related Article: Things to do in Door County Wisconsin

Lunch: Sobelman’s

Stop into Sobelman’s, a Milwaukee Landmark, for lunch and possibly the world’s largest Bloody Mary. The bloody’s here are a meal in themselves with a whole spread of food artistically skewered and perched on top of a pint glass.

Even though most Bloody Marys come with a slider sticking out the top, Sobelman’s burgers are not to be missed. A trip to Sobelman’s pairs well with a Brewer game the Brew Crew plays just down the road. However, game days can be quite busy here.

  • Address: 1900 W St Paul Ave, Milwaukee
Girl with the Fonze statue in Downtown Milwaukee

Take a Selfie with the Fonz

If you’re of a certain generation, you’ll want to schedule a few minutes out of your time in Milwaukee to pay a visit to one of its most famous residents, the Bronze Fonz.

Arthur Herbert Fonzarelli’s character from the TV series Happy Days is immortalized in bronze along the banks of the river in downtown Milwaukee. The show was set in Wisconsin, hence the connection to the city and state.

  • Located: On the Riverwalk Way just off of Wells St
Pedal Tavern Boats in the Milwaukee river - things to do on a weekend in Milwaukee

Pedal Tavern

With selfies out of the way, spend your afternoon aboard one of the most unique modes of transport in Milwaukee – The floating pedal tavern.

You may have seen peddle taverns in other cities, but in Milwaukee, we have one that is outfitted with a giant old-timey paddle wheel, and you and your group peddle the paddle down the river, stopping at riverside bars.

Dinner: The Safe House

To keep the quirkiness levels high, make plans to have dinner in a cold war era-inspired spy bar in Downtown Milwaukee. Inside the doors of this unassuming and relatively unmarked building sits a hidden spy lair that serves food and drinks – BUT, there’s a catch.

You have to know the password to get in. If you know the phrase, you’ll be ushered through a set of very spy-like doors, but if you don’t, you’ll have to pass a bunch of interesting tests that are sure to amuse the guests already inside who will be watching on the CCTV.

Once inside, you’ll notice the maze of old-time mail delivery tubes used for drink delivery here, and make sure to have your martini perfectly shaken, not stirred. If you aren’t hungry yet, it’s still a fun place to grab a drink.

After dinner, if you are still looking for some more entertainment, make the short trip down to Old World Third Street for some of the city’s most unique bars.

If you’d prefer to know the password in advance, send us a message.

  • Address: 779 N Front St, Milwaukee

Sunset at Milwaukee Art Museum - Top things to do in Milwaukee - Weekend getaway

Day 3 – Artistic Side of Milwaukee

If you’re an early riser, start your day down at the lakefront to take in the sunrise. If you like travel photography, this is one of the best times to get some great shots of Milwaukee.

Most mornings, the skies over Lake Michigan light up in soft pastel colors for a few breathtaking moments.

A great subject to put in your frame is the sweeping lines on the Milwaukee Art Museum alongside the colorful early morning. Unfortunately, most of Milwaukee’s main attractions don’t open for another few hours past sunrise, but take the time and grab a coffee or breakfast.

Breakfast: Collectivo Coffee (Lakefront Location)

Just down the road is one of Milwaukee’s favorite coffee shops Collectivo Coffee, located right across the street from the lake and marina. This old cream city brick building was once part of the public waterworks system in Milwaukee but now serves up some great coffee and light meals.

The Milwaukee Art Musem – MAM (pictured above)

After fueling up with some coffee, make your way back down to the lakefront to go inside the Milwaukee Art Museum. Whether you are an avid art viewer or not, the MAM has something for just about everybody. The sweeping organic lines of the bright white entrance and exhibit hall are a work of art itself.

To add to the interest – it moves. “The Wings,” as most have dubbed them, are a series of beams that move up and down on a motorized system. If you want to see this unique building in action, make your way outside to the front of the building at noon each day for the show. In Milwaukee, we love this building. It has become the symbol of the city.

Historic Old Third Ward

Spend your afternoon perusing the many interesting and eclectic shops of Milwaukee’s Historic Third Ward. The Third Ward has no shortage of restaurants, bars, and trendy shops.

We suggest strolling through the Milwaukee Public Market and grabbing a mid-morning snack or picking up a souvenir t-shirt at the MKE Home store.

Make sure to check the events calendar and see if there is a festival down at the Summerfest grounds. If you’re there during the Summerfest it’s a must to catch a free concert or two. We always enjoy a peaceful walk on the Riverwalk before making our way to lunch.

Milwaukee Ale House Brewery Milwaukee riverfront

Lunch: Milwaukee Ale House

One of the best places to end your trip to Milwaukee is on the Milwaukee River at the Milwaukee Ale House. There are several restaurants along the Riverwalk, but we love the Ale House.

As the name suggests, they are a brewery that serves up some tasty beers to go along with lunch. Some of our favorites on their menu are cheese curds, burgers, and chicken pot pie. They also have great weekday lunch specials.

  • Address: 233 N Water St, Milwaukee

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pinterest pin for weekend getaway in Milwaukee Wisconsin - City skyline at sunset


Tuesday 13th of April 2021

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Thursday 13th of May 2021

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