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Bradford Beach on Lake Michigan is America’s most accessible beach.
Everyone has their season. Because I live in the Deep South, fall is mine. When the cranky summer storms fizzle and the beach crowds scatter, I feel myself come alive again. Cities, I think, like people, also have their moment, when their most special, indelible traits come out in full force.
Last June, I found that to be true of Milwaukee. I was fortunate enough to be invited by Visit Milwaukee for a three-day FAM that culminated with SummerFest, the world’s largest music festival. Running over three weekends, it is the pinnacle of Milwaukee’s packed events calendar, which has something to appeal to every interest, culture, and whim — VeganFest, Irish Fest, Mexican Fiesta, to name a few. In total, the city sees more than 100 annual festivals every year, with many happening in the summer to take full advantage of the comfortably warm, but thanks to Lake Michigan, breezy days.
That’s what pleasantly surprised me the most when I first arrived in Milwaukee. Instead of a wet wall of humidity smacking me in the face, I stepped out of the airport into a tepid, 70-degree day. To this wilted Southerner, it felt like dipping into a cool lake.
Checking All the Boxes
Even though it was a Tuesday afternoon as we drove through downtown Milwaukee, the city felt energized — buzzy, even. Everywhere I looked, people strolled, biked, and sunned themselves on patios, crisp beers in hand.
In 2025, economic impact generated by Milwaukee County’s tourism industry surpassed $4.4 billion, helping Wisconsin break its fourth consecutive record for tourism. It’s an achievement owed to those many local festivals but also to a growing number of business and sporting events. Among them, the 2025 and 2026 USA Triathlon Sprint and Olympic-Distance National Championships and the 2025 USA Fencing Summer Nationals, the world’s largest fencing tournament — wins bolstered by the city’s impressive number of pro sports teams and facilities. But there are major conventions to note, too, like the 2024 Republican National Convention, which put the city on a national and global stage.
Examples like these show that “Milwaukee isn’t just competing with cities in its consideration set anymore,” Raymond Valles, national account executive at Visit Milwaukee, tells me that evening during a welcome reception hosted by the DMO. We’re enjoying drinks outside at The Yard, an outdoor space at the industrial-chic Iron Horse Hotel, where Harley-Davidson fans (and rumor has it, SummerFest headliner Ed Sheeran) post up. Milwaukee, Valles says, now lures groups that typically book larger destinations. 2026 saw Milwaukee play host to several high-profile industry gatherings, including the upcoming International Food Wine and Travel Writers Association in October and Expo! Expo! IAEE’s Annual Meeting & Exhibition in November.
Take a lap around Milwaukee’s convention district and it becomes immediately clear why: Milwaukee checks the big boxes, with modern hotels and sleek event facilities in a safe, compact downtown. But it comes without the sticker shock of destinations twice its size. Not to mention that Milwaukee is convenient in ways many cities are not. For instance, the drive from the airport to my downtown hotel took a paltry 15 minutes.
It helps, too, that a good meal is easy to find. After our welcome reception, our group lingered for hours over steak and wine at Cassis, a newish French bistro in the hip Third Ward from James Beard Award–nominated chef Kyle Knall. Cassis has already earned a nod from Bon Appétit on its list of “9 Must-Visit Restaurants to Try in 2025.”
The bar is high here for casual eats, too. During lunch on our second day at Milwaukee Public Market — held in Madame Kuony’s Kitchen, an upstairs private event space with a demonstration kitchen — our group grazed on empanadas, lobster rolls, mezze, and brats, a feast of global flavors representing the impressive diversity of the market’s vendors.
For its near $500-million transformation completed in 2024, the team at Baird Center surveyed planners on what features mattered most to them.
Main Character Moment
Just a half-mile from Milwaukee Public Market is another good-for-groups option packed with Milwaukee flavors: 3rd Street Market Hall, just across the street from Baird Center. When I last visited Milwaukee in 2023, Baird Center was still under construction. Seeing the convention center in its final form today — a striking building filled with light and art — stopped me in my tracks.
The building’s “collaborative staircase” catches my eye first when I enter the lobby. Wide enough to serve as casual seating, the staircase is made from local salvaged ash wood and represents one of many artistic manifestations of Milwaukee and the wider Great Lakes region within the center. Another favorite is “The Great Five” by Bluworld of Water, a multistory installation of water cascading down five steel panels, each of which represents one of the Great Lakes.
The more I see of Milwaukee, the more I understand that the Great Lakes are a main character in the destination’s story. At Discovery World, the state’s largest aquarium, the Freshwater Sustainability Lab exhibit shows the importance of the Great Lakes as a fresh water supply and why it’s important to protect them. Proximity to the mineral-rich waters of Lake Michigan played a key role in the creation of Milwaukee’s prolific brewing empire starting in the 1800s, producing household names like Miller and Pabst. But the lakefront also serves as an important source of social connection. Milwaukee’s miles of shoreline provide some of the city’s most popular activities and gathering places, like the bustling 3.1-mile RiverWalk, which follows the Milwaukee River, and Henry Maier Festival Park on Lake Michigan.
The 75-acre Henry Maier Festival Park is the home of SummerFest (and countless other festivals) and is where we spend our last evening in Milwaukee, bouncing between sampling the creative offerings at food stands (birria egg rolls, anyone? I was a fan) and catching sets at the festival’s dozen stages. It wasn’t until the sun faded behind Lake Michigan that we finally took our seats in the park’s amphitheater, already packed shoulder to shoulder. I could feel the energy of the crowd, brimming and eager for Sheeran to take the stage. So fitting, I thought, for a city finding its place on the stage, too.
Milwaukee suburb Wauwatosa in home to the North Avenue Mural Arts District.
A Wander in Wauwatosa
This charming Milwaukee suburb is well worth the slight detour from downtown. Tosa — as the locals call it — is beloved for the colorful artwork adorning the walls of the North Avenue Mural Arts District as well as many mom-and-pop shops and eateries. After sharing a box of doughnuts at Cranky Al’s, we perused the shelves at The Well Red Damsel, a fantasy and romance-focused independent bookstore with a local cult following. In nearby Firefly Grove Park, fans of artist Thomas Dambo flock to see his first troll sculpture in Wisconsin, Mama Rosa, a 25-foot-tall troll crafted from recycled wood.
Well Accommodated
Of Milwaukee’s 20,000-plus hotel room inventory, a third is located downtown. Below, our take on three event-friendly properties we visited during our FAM:
› The Iron Horse Hotel — A little bit industrial, a little bit funky, this boutique property has a big personality and spaces to match. My oversized Comfort Deluxe King room came with river views and easy access to the nearby Harley-Davidson Museum.
› The Pfister Hotel — This AAA Four-Diamond property in the Third Ward wrapped a major renovation in 2025, but the star of this 130-year-old building is the ornate art and interior design, including the largest Victorian art collection of any hotel in the world.
› The Trade, an Autograph Collection Hotel by Marriott — This 207-room hotel adjacent to Fiserv Forum is primed for professional athletes (literally, designers retrofitted an entire floor of guest rooms to better suit tall basketball players), but planners will love the modern, sleek meeting spaces and walkable location.
Jennifer N. Dienst is senior editor at Convene