Your Guide to Milwaukee, An Underrated Midwest Escape – Neckies Great Adventures

Beer, brats, cheese, and a Great Lake; when you think of Milwaukee, chances are these are the first things to come to mind. And while it’s certainly true that Milwaukeeans have a penchant for brews and local dairy products, there is so much more in this great city waiting to be explored. From spacious historic parks and a vibrant local sports scene to delicious food offerings and adorable shops and boutiques, Milwaukee, while often overshadowed by Chicago to its south, is worth a visit.   

Are you thinking about making Cream City your next Midwest escape.  Here are some tips to help you get started.

A Brief Overview of Milwaukee Neighborhoods – Shorewood

A charming village in Milwaukee County, Shorewood borders Milwaukee’s East Side to the south and Whitefish Bay to the north. The neighborhood is a mix of residential housing, small businesses, and popular retailers — including Metro Market and Culver’s —many of which are along the main drag on North Oakland Ave. Local recommendations for this area include:

• Grabbing a drink at Camp Bar.
• Spending an afternoon at Atwater Park.
• Enjoying dinner or a coffee at one of the many local restaurants.

The East Side

Divided into “upper” and “lower” portions, Milwaukee’s East Side is an expansive neighborhood with popular attractions like the University of Wisconsin Milwaukee, bustling Brady Street, and beautiful Lake Park. Locals and visitors enjoy unparalleled views of Lake Michigan with quick access to lakefront attractions like Bradford Beach, Veterans Park, and Lake Park. Local recommendations for this area include:

• Devouring a late-night slice at Ian’s Pizza.
• Making the most of fleeting summer days with a bike ride on the Oak Leaf Trail.
• Watching a movie at the Oriental Theater.

Riverwest

Situated west of the Milwaukee River, Riverwest is bordered by the East Side to its east and Bronzville to its west. This unique neighborhood is filled with craft breweries, cycling enthusiasts, and charming dive bars, giving it a “hipster” reputation. Local recommendations for this area include sampling beers from local breweries like Amorphic and Black Husky, visiting iconic bars and restaurants like Art Bar, Two, and Cafe Corazon, and participating in the Riverwest24, a 24-hour bike ride the entire weekend of July.  

Bronzeville

Comprising of areas like Haymarket, Brewers Hill, Harambee, Halyard Park, Schiltz Park, and the Bronzeville Cultural Arts and Entertainment District, Bronzeville once acted as a mecca for Black businesses and entertainment before being displaced in the 1960s due to highway construction. Today, Black business owners and creatives are reclaiming their history through new attractions like museums, restaurants, and shops. Recommendations from a local include:

• Learning something new at America’s Black Holocaust Museum.
• Embarking on a flavorful journey at Dead Bird Brewing.
• Browsing handcrafted goods at The Bronzeville Collective MKE. 

Wauwatosa

Referred to by locals simply as “Tosa,” Wauwatosa is a trendy neighborhood west of downtown Milwaukee. This region boasts convenient access to I-41, and visitors will find popular attractions like the Milwaukee County Zoo and Mayfair Mall in addition to cozy spots like the Tosa Village — with its abundance of bars and restaurants — and sprawling green spaces like Hoyt and Hansen Parks. Recommendations from a local include:

• Exploring colorful murals.
• Sinking your teeth into an iconic treat at Cranky Al’s.
• Supporting small shops and boutiques.

West Allis

Wauwatosa borders home to Wisconsin State Fair Park, West Allis to its north, and Walker’s Point to its east. Close to American Family Field, this part of Milwaukee is popular among Brewers fans, who will find plenty of convenient spots to fuel up before a game on Miller Parkway. Recommendations from a local include:

• Trying a new brew at Perspective Brewing Co.
• Embracing Wisconsin’s German roots at Kegel’s Inn.
• Spending a morning at the West Allis Farmers Market.

Walker’s Point

Famous for its nightlife, restaurants, and LGBTQ+-friendly vibes, Walker’s Point is a vibrant and diverse neighborhood southwest of Milwaukee’s trendy Third Ward. Here, visitors can enjoy views of Milwaukee’s Harbor, hop aboard a peddle tavern, or get creeped out on a ghost tour at Shakers, Milwaukee’s haunted bar. Recommendations from a local include:

• Dining at Zocalo Food Truck Park.
• Grabbing a drink at Boone + Crocket.
• Visiting Don’s TV & Repair Speakeasy for a decadent adult milkshake.

Downtown

Home to Fiserv Forum, the Milwaukee Public Museum, and several theaters and arenas, downtown Milwaukee is a hub for fun and entertainment. Whether they spend time exploring the abundant bars and eateries, catching a basketball game in the Deer District, or heading toward the lake to visit the Milwaukee Art Museum, there’s always something going on downtown. Recommendations from a local include:

• Posing by the Bronz Fonz along the Milwaukee River.
• Enjoying an Edelweiss cruise in the summer.
• Visiting 3rd St Market Hall.

The Third Ward

Located just south of Milwaukee’s major lakefront attractions like the Milwaukee Art Museum and the Summerfest grounds, the Third Ward emits a big city feel with its artsy turquoise light fixtures, expensive boutiques and shops, and excellent walkability. The neighborhood is a hit among tourists and locals, especially the famous Milwaukee Public Market. Recommendations from a local include:

• Riding The Hop (Milwaukee’s free-to-ride streetcar).
• Taking a stroll along the riverwalk.
• Playing pickleball at the courts beneath the interstate.  

Bayview

A quick drive across the city’s iconic Hoan Bridge (794) will take visitors to Bayview, a quirky neighborhood where locals joke hipsters go to retire. As such, travelers can expect no shortage of cozy restaurants and bars, one-of-a-kind boutiques, and eclectic shops, many of which line Kinnickkinnick Ave, Bayview’s main drag. Recommendations from a local include starting a night out at bars like the Sugar Maple, the Mothership, and At Random, looking for your next fantastic gift at shops like Sparrow Collective, and taking a quick drive to nearby South Shore Park. 

Getting Around

As a mid-size city, getting around Milwaukee is relatively easy. However, the area is predominantly car-dependent, so visitors looking to cover lots of ground will want to either rent a car from Milwaukee Mitchell International Airport (MKE) or plan to utilize ride-sharing apps like Uber and Lyft. Alternatively, visitors planning to stay near the lakefront or in one specific neighborhood can take advantage of bikeable streets and the Oak Leaf Trail, which connects a variety of Milwaukee County Parks to the lakefront and beyond.

For a quick day trip to Chicago, Milwaukee offers convenient access to two Amtrak stations — one downtown at the Milwaukee Intermodal Station (MKE) and one that boards at the airport (MKA). From the Milwaukee Intermodal Station, visitors also have the option to explore neighboring parts of Wisconsin via regularly scheduled buses operated by Amtrak.

By the Seasons

It’s no secret the weather in Milwaukee can be a rollercoaster. From seemingly endless winters that stretch into April to hot and muggy summers that will have you reaching for the A/C, Wisconsin’s Fresh Coast keeps residents and visitors on their toes. Despite this, there’s something fun to do in Milwaukee year-round; you need to know where to look. 

In the Spring

From March through May, the occasional snowy day (or snowstorm) is still to be expected. However, slowly but surely, the sun begins to make its highly anticipated return. Here are a few ways to make the most of your visit during this time. 

• Museums: The perfect antidote to lingering dreary days, Milwaukee’s many museums offer a fantastical escape. For art lovers, there’s the Milwaukee Art Museum, with its sweeping views of Lake Michigan and unique architecture. Discovery World is a science and technology museum with plenty of hands-on activities for those visiting with their children.
• And, for travelers of all ages, there’s the Milwaukee Public Museum with its immersive displays and abundant artifacts. Finally, while not technically a museum, the Mitchell Park Domes is also worthy of a shoutout, a conservatory filled with colorful desert and tropical plants.

• Food Halls: Showcasing the best of local restaurants and businesses, Milwaukee is home to a bounty of food halls. The Milwaukee Public Market in the Third Ward is always famous for its selection of dining options, gifts, fresh produce, and Wisconsin-made cheese. Other must-visit options include 3rd St Market Hall near Fiserv Forum, Crossroads Collective on the East Side, and Sherman Phoenix to the north.

• Milwaukee Brewers Opening Day: Each year in early April, Milwaukeeans experience their first taste of summer when American Family Field hosts the Milwaukee Brewers’ Opening Day. Visitors want to show up a few hours before the game for some tailgating, complete with beer and brats, to fit in with the locals.

In the Summer

Summer is in full swing from July through August, and MKE residents are out and about, eager to take advantage of sunny days and humid nights. Here are a few ways to make the most of your visit during this time. 

• Beer Gardens: True to its German roots, the city of Milwaukee and its inhabitants love their beer. During the summer, beer gardens are at their greatest with charming string lights, live polka music, and no shortage of brews on tap. Check out Estabrook Beer Garden, Hubbard Park, Juneau Beer Garden, South Shore Terrace, The Landing at Hoyt Park, and more.

• Fun by the Lakefront: When the weather gets hot, the Milwaukee Lakefront comes alive. From sunbathing and volleyball at Bradford Beach to kite flying and biking at Veterans Park, summer in MKE is a vibe.

• Summerfest: Of course, it wouldn’t be summer in Milwaukee without Summerfest, the city’s annual music festival that held the title of “The World’s Largest Music Festival” until 2015. The event attracts top talent each year, making it a must-do for music lovers throughout the Midwest.

In the Fall

The summer heat gives way to crisp fall days from September through November. As the leaves change, a familiar thrill and the smell of pumpkin spice fill the air. Here are a few ways to make the most of your visit during this time. 

• Doors Open: A must-attend event for history buffs, each September, Historic Milwaukee, Inc. hosts Doors Open Milwaukee, a two-day celebration of the city’s architecture, history, and neighborhoods through 100+ free tours in the metro area.

• The Milwaukee Bucks: After winning the NBA Championships in 2021, the Milwaukee Bucks are a significant source of pride for residents of Cream City. Visitors can attend a home game at Fiserv Forum anytime between late October and early April to get in on the action.

• Milwaukee Paranormal Conference: Travelers looking to embody the “spooky” in Spooky Season won’t miss their chance to attend the annual Milwaukee Paranormal Conference. Traditionally held in mid-October, this festive event is unlike any other, with lectures, activities, and more surrounding the strange and unusual. And, best of all, it’s free.

In the Winter

From December through February, winter has moved it, but the brisk days and long nights don’t slow Milwaukeeans down. Instead, the city keeps busy with seasonal light displays, cozy hideaways, and outdoor fun. Here are a few ways to make the most of your visit during this time. 

• Stay Warm Indoors: Let’s face it: going outside when the air hurts your face isn’t for everyone. To combat sub-zero temperatures, look for fun indoors at one of Milwaukee’s many entertainment venues, like North South Club for shuffleboard and axe throwing, RSVR for virtual reality fun, and Up Down for arcade games and drinks. In addition to activities to keep busy, visitors will find comfort in toasty retreats throughout the city, like the At Random cocktail bar, Lake Park Bistro, and local coffee shops.

• Ice Skating: A tradition for many years, hundreds of people flock downtown to Red Arrow Park each winter to test their skating skills.

• Seasonal Light Displays: A time when winter nights are aglow, each December, Milwaukee plays host to various seasonal light displays. From Wild Lights at the Milwaukee County Zoo to Winter Wonders at the Boerner Botanical Gardens, the city has no shortage of holiday cheer. 

Milwaukee is a city that has something to offer for everyone, no matter the season. Whether you want to explore the diverse neighborhoods, sample local cuisine, or attend some of the city’s many festivals and events. With this guide to the city’s neighborhoods and seasonal activities, you’ll have an unforgettable visit to Cream City. So, pack your bags, grab your coat, and get ready to experience all that Milwaukee offers!