Weekend Getaway: A Guide to Milwaukee, Wisconsin

Welcome to our Weekend Getaway series! While it’s our preference to discover a country slowly and thoroughly, realistically time often only allows for a long weekend of exploring. Each week we’ll focus on a different city and highlight how to get the most out of a 2-4 day stay. Sometimes we write about the city ourselves, while other times we’ll have awesome guest bloggers giving us the low-down.

If you’re interested in guest blogging on this series, shoot us an email!  

A Weekend Getaway To 

What makes Milwaukee a good place for a weekend getaway?

In the last few decades, residents of Milwaukee have been striving to turn their dilapidated buildings and industrial reputation into that of a hip, up-and-coming city. With cool events and exciting happenings, they’ve been doing a great job of invigorating this Wisconsin city. 

What’s the best way to travel to Milwaukee

As with most places in the US, it’s easiest just to fly straight into Milwaukee’s General Mitchell International Airport. It is relatively small (especially when compared to nearby Chicago O’Hare and Midway Airports) and easy enough to get around. In 2005 an Amtrak route opened up between Chicago and Milwaukee however, so if you find yourself with a much cheaper flight into Chicago, you can grab yourself a cab/Uber ride to Union Station, then purchase a train ticket for the hour and a half ride for around $25. 

Public transportation: Is it available in this city, and is it easy to navigate?

The US can get so many things right, but one of the things it gets wrong is public transportation… for the most part. Milwaukee is average as far as a US city is concerned. The Milwaukee County Transit System is a bus line that covers the city and has around 50 routes available. You can either use exact change or purchase a MCTS M-Card if you think you’ll be using the bus frequently. Click here for prices and variations of the M-Card.

If the bus line isn’t your style, you’ll pretty much be limited to rental cars, cabs or Uber rides.

What is the typical cost of a taxi to get from one side of town to the other?

A yellow taxi cab, from the General Mitchell International Airport to downtown Milwaukee, will cost you around $30.

Do you have any recommendations on a luxury or boutique hotel in the area?

Converted from a 100-year-old warehouse, the Iron Horse Hotel is an awesome property. Technically it could be considered both a luxury and boutique. The hotel features 100 spacious loft-style rooms and caters to both the business person and the biker. Guest rooms have exposed brick walls, huge windows, large timber posts, and wooden floors. It is a unique offering for a hotel, and it’s not contrived; it’s genuine! Rates start as low as $169 per night.

For a more classic luxury hotel, look up the Pfister Hotel. Built in 1893, this elegant property has been a mainstay of the Milwaukee area for over 120 years. The interior looks like the inside of the Titanic; you can almost imagine Jack and Rose and their saucy shenanigans. Rooms start at around $249 per night.

How about those looking for a more budget friendly option? 

Milwaukee doesn’t seem to offer any hostels yet, however if you’re looking for something super cheap, the Econo Lodge Hotel Milwaukee Airport might be a good option for you. Rooms start around $30 per night for the standard rooms. Normally these kinds of places can be pretty sketchy, but they are rated well for their cleanliness. They also offer a complimentary 24-hour shuttle service to the airport, which is a great bonus!

Couchsurfing and airbnb are also great alternatives! 

One of our favorite things to do while exploring a new city is to take part in the outdoors scene. What are some adventure and/or outdoors activities (such as hiking, biking, waterfall rappelling, skiing, skydiving, etc.) to enjoy here?

There are a few pretty cool things to explore during your time here. Since Milwaukee is located right on the shoreline of the enormous Lake Michigan, plenty of the outdoor activities revolve around the water. 

The Lakefront Trail is exactly what it sounds like: a trail that juts right up next to the lake. It is very scenic, and during the months of good weather, the trail can be jam-packed with joggers, walkers, roller skaters, and many other -ers. Oftentimes families will sit in the grass to the side for a picnic. The trail passes by the Milwaukee Art Museum, Veteran’s Park, and the McKinley Marina. 

There are plenty of rentals available as well. You can rent bikes and skates for the Lakefront Trail, or if you’d rather get onto the water you can rent a kayak. Since the river runs right through the middle of town, you’ll be able to kayak right alongside the historic waterfront. 

Probably the coolest sounding of anything though, is SCUBA diving. Squeeze into a wetsuit and strap on your underwater breathing apparatus to get up close and personal with some real-life shipwrecks in Lake Michigan. Swimming to the depths of the lake, you’ll get the chance to see a few shipwrecks, some nearly 150 years old!

Are there any local entertainment events that we should know about when planning a trip to Milwaukee (such as South By South West in Austin, a Football match in England, or running with the bulls in Spain)?

Why yes, there is. Easily Milwaukee’s largest event, Summerfest attracts around a million people to its 12 different stages. The “Guinness World Records” book has officially recognized Summerfest as the largest music festival in the world! The event spans 11 days in late June through July, and features solo artists and groups such as the Rolling Stones, Kings of Leon, Carrie Underwood, and hundreds of other popular artists.

Name one phenomenal attraction that shouldn’t be skipped.

When I was in Milwaukee a few years ago, we kept hearing whisperings of a place called the Safe House, a “secret” bar and restaurant fixed up Prohibition-style. Our rowdy group crammed into a taxicab, and the driver dropped us off in a deserted, sketchy-looking alleyway. We walked up to the doorway, where a woman sat dressed in 20’s garb.

I won’t ruin the surprise for you because you should experience it for yourself, but after a few embarrassing minutes trying to guess the secret password, we were finally let in. The place was bigger than it appeared, and the restaurant was filled with families enjoying their meals. We followed the endless hallways toward the back, went through a secret door, and finally found our way to the bar. Decorated in a super eclectic way, Safe House had a cool, laid-back atmosphere and we had a great time for the few hours we spent there.

Another popular attraction is a brewery tour, and there are a few to choose from. Milwaukee Brewing Company and Lakefront Brewing Company both offer tours that are funny yet informational, allow you to drink samples and even give you a free pint glass included in the cost of the tour. 

Where should I go if I want to blend in with the locals?

Arguably the best sports bar in Milwaukee would be Major Goolsby’s, where locals go to watch the Brewers, soccer, March Madness… you name it. Located just a block from the Milwaukee River and a few blocks the other direction from Marquette University, Major Goolsby’s provides a great atmosphere, a highly-praised selection of food and plenty of televisions; everything you’d want in a sports bar.

For a more relaxed/upscale time, head on over to Whiskey Bar. With dim lights, soft leather furniture and, as the name implies, a large selection of whiskeys to choose from, Whiskey Bar is the perfect solution for a quiet night of drinks. 

Let’s talk about an important aspect of travel: Food. What are your absolute favorite restaurants in the area?

Milwaukee is a city with a lot of great restaurants that serve seafood, steaks and plenty of local beer. Mr. B’s was named one of the 45 best steakhouses in the country, so if that’s what you’re hankering for then it’d be hard to pass this place up.

For some authentic Italian, look up Glorioso’s Italian Market. Here you’ll find huge selections of meats, cheeses, sub sandwiches, sandwiches, cannolis… really anything Italian you can think of. It is very popular and for good reason!

For one of the best brunches in town, look no further than Blue’s Egg. There will more than likely be a 30-60 minute wait, so be sure to get there early to beat the rush! If you search for reviews of this place, you’ll be astonished at all the 5-star ratings. 

What’s one local dish you’d recommend someone to try while they’re here?

Try the Friday fish fry found at Serb Hall, which has been served continuously since the 1960s. 

If you’re looking for something sweeter, head on over to Kopp’s for some frozen custard!

We’re from the US where waiters and waitresses make a living solely from tips. What is the tipping etiquette in Milwaukee?

15-20% is standard for waiters and waitresses in the U.S.

If we’re craving a night out on the town, what are some cool local spots we should check out?

Jynx Nightclub is a relatively new fixture of Milwaukee and was voted best nightclub of 2014 by locals. The owners consistently get high praises for providing great service, awesome atmosphere and even better DJs. 

Anything we should know about the local culture and customs (so you don’t offend people, or get offended by something!) 

As with most sports towns, you probably shouldn’t antagonize fans of the Brewers (baseball) or the Bucks (basketball), otherwise you could find yourself at the business end of a fist sandwich. 

What is the currency here and how much would a typical pint of beer cost or glass of wine cost?

The U.S. Dollar is the currency (although some would argue beer IS the currency), and a typical pint of beer will set you back $5-$7. 

Did you enjoy this weekend getaway guide? Let us know in the comments below or by sharing it on social media! We love hearing from you 🙂 

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Cheers, 

Jimmie & Shelly