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An Out-Of-Towner’s Guide to Milwaukee

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REI Midwest Turnkey Investment Properties

For the record, I don’t consider myself an out-of-towner to Milwaukee. I’m more like a commuter, a very long-distance commuter.

Since 2012 I’ve traveled from our office in Gilbert, Arizona to Milwaukee approximately 50 times (click here to see why our firm chose to invest in the Milwaukee real estate market). Because I usually stay at least three nights while in town that equates to over 150 sleeps in 10 different hotels, from Waukesha to Brookfield to downtown.

I also go out to eat three times a day on these business trips. That means about 600 meals in the greater-Milwaukee area. I refuse to dine at the national chain restaurants. I get recommendations from Milwaukeeans.

So why would an out-of-towner like me have the nerve to write a post like this?

With multiple remodeling projects around the city, including South Milwaukee, West Allis, Waukesha, Brookfield, Wauwatosa, Riverwest, Shorewood and Whitefish Bay, I get to see and learn a lot about what makes this corner of Wisconsin so special. I guess this gives me a unique perspective of the area.

Certainly I’m no foodie, culinary aficionado or lifestyle expert. However, I do like to eat and find interesting things to do when I’m not working. The truth is while in town I’m mostly meeting, eating, sleeping or exercising. So without any more delay here are some of my favorite places to do those things:


Colectivo Coffee Riverwest REIMidwest

Colectivo Coffee – Riverwest

We don’t have a physical office in Milwaukee, yet. So when I need a cozy, comfortable place to check my email, make phone calls or just relax I prefer the Colectivo Coffee Riverwest location. While Colectivo has several coffee houses throughout the city this one is my favorite.

Colectivo Coffee Riverwest REIMidwest Turnkey Investment PropertiesI stumbled across it a few years ago after we purchased a duplex about a block away. They roast their beans at the Riverwest location and you can smell the aroma in the parking lot as you walk in. The clientele is eclectic too; the place has a mix of Moms, college professors, students, hipsters and young professionals. For breakfast I recommend the baked oatmeal or chorizo burrito. At lunch try the vegetarian white bean chili. The berry booster makes an excellent snack. Oh, and don’t forget the coffee. It’s delicious.

Address: 2999 N. Humboldt Blvd, Milwaukee, WI 53212 

Jackson Grill REIMidwest Turnkey Investment Properties

Jackson Grill – Milwaukee

Located on the corner of 38th Street and Mitchell, Jackson Grill has a modest but charming exterior. You’d never know from driving on Mitchell Street from 43rd Street past the industrial buildings and bus yard that one of Milwaukee’s top steakhouses awaits (they call it a supper club). You’ll have to park along the curb in front of the building or the next block over.

Jackson Grill Bar REIMidwest Turnkey Investment PropertiesInside Kevin, or one of their other friendly bartenders, will offer you a cocktail while you wait for a table in the dining room (reservations recommended). Above the bar there’s a unique collection of glass sculptures that the owner’s wife has collected over the years. On the walls of the lounge are chalkboard signatures of famous locals like Bob Uecker and Bud Selig.

I prefer to eat at the bar, chat it up with Kevin and feast on their filet mignon with signature Portobello mushroom, garlic mashed potatoes and salad with peppercorn dressing.

Address: 3736 W. Mitchell Street, Milwaukee, WI 53215


Screaming Tuna Third Ward REIMidwest Turnkey Investment Properties

Screaming Tuna – Third Ward

Located at the confluence of the Milwaukee and Menomonee Rivers in the Third Ward, Screaming Tuna has great views and sushi. There’s no shortage of restaurant options in the Third Ward, however this is one of my top places to eat when staying downtown. My wife and daughters won’t eat sushi so when I travel alone I crave a fresh roll and smoked salmon.

They don’t have much of a parking lot so plan to park on the street and walk a block or two. But it’s worth it. I’ve tried about half the menu and everything is fresh and tasty. My favorites are the Spiderman Roll and the Signature Roll.

Address: 106 W Seeboth St, Milwaukee, WI 53204


Milwaukee Public Market REIMidwest Turnkey Investment Properties
Milwaukee Public Market – Third Ward

When it’s cold outside, or raining, the Milwaukee Public Market is an excellent place to hang out, shop, drink and of course, eat. Also located in the Third Ward, this indoor market has just about everything – a butcher counter, candy store, seafood restaurant, bakery, cheese and sausage shop and spice house.

Thief Wine REIMidwest Turnkey Investment PropertiesUpstairs they have lots of seating for eating and drinking, which includes a bird’s eye view of the entire building and the Milwaukee River to the west. It’s from this elevated location that I spotted Thief Wine, one of several small bars also in the market. I prefer their Artisanal Charcuterie Plate (lots of meat) and whatever red wine the bartender recommends.

Address: 400 N. Water Street, Milwaukee, WI 53202

InterContinental Hotel Lobby REIMidwest Turnkey Investment Properties

InterContinental Hotel – Downtown

I can’t stand spending a lot of money on a hotel, especially when traveling for business. There’s really no reason to splurge since so little of my time is actually spent in the room or using the amenities. That said location is important because we own properties all over the city. I like to be centrally located so the downtown area makes the most sense. At night I don’t want to drive anywhere because I’ve been traversing the greater-Milwaukee area all day.

There’s so much to see and do on both sides of the river and the downtown area is fairly compact. That means lots of dining and entertainment options are within walking distance of just about every hotel.

InterContinental Hotel REIMidwest Turnkey Investment PropertiesI’ve found the best value to be the InterContinental Hotel. Inside, the lobby and bar are very contemporary and the staff is friendly. There’s a Vegas feel to this place.

I like to workout in my room so I need more space than some of the older hotels offer. The rooms at the InterContinental are more spacious. Like the lobby and bar, they also feel more modern, which I prefer to the historic look.

The fitness center has all the basics and their Kil@Wat Restaurant, located on the second floor, has an excellent breakfast, lunch and dinner menu. The hotel is also connected to the Pabst Theater, so if there’s a show or comedian I want to see in town I don’t even have to walk outside of the building.

Address: 139 E Kilbourn Avenue, Milwaukee, WI 53202

Oak Leaf Trail - runner - REIMidwest Turnkey Investment Properties

Oak Leaf Trail – The Lakefront

I wouldn’t say that I’m a fitness buff, but I do enjoy exercising (mostly when it’s over).

While I’m in town (and I’m not working AND it’s warm enough) you’ll find me running along the Oak Leaf Trail, which starts at the corner of Prospect Avenue and Mason Street. This trail goes along the lakefront and eventually turns inward towards the north side of downtown and then along the Milwaukee River.

Oak Leaf Trail head - REIMidwest Turnkey Investment PropertiesNot only is the scenery absolutely beautiful the trail is full of runners, bikers and walkers of all ages. What’s most impressive is that these people aren’t fazed at all by the weather. Even when the temperatures dip below 20 degrees you’ll find fitness nuts of all ages on the trail.

But I’m not one of them. My rule is if the outdoor temperature is below my age then I hit the treadmill.

Address: Corner of Prospect Avenue and Mason Street, Milwaukee, WI

In three years I’ve discovered a lot about the greater-Milwaukee area. It’s been an immersion course in history, geography, real estate, business and culture. And while my company doesn’t have an office there and I have no permanent residence I still consider Milwaukee a second home. I often tell people I know more about what’s going on there than I do in Arizona.

If you’re reading this and you’re a Milwaukeean let me know what else I should see while in town. I’m there about every other week so I’m always looking for something new to explore. If you’re considering a trip to Milwaukee, for business or pleasure or both, now you have a few things to put on your to-do list.