In A-side/B-side, two Milwaukee Record writers tackle various city issues in an informal, crosstalk style. Insults are hurled, feelings are hurt, and everyone learns something in the end. Maybe.

Matt Wild: Hey Tyler! Long time no crosstalk! It may be a bit early to talk about the 2024 Great Milwaukee Summer, but some recent summertime news has been stuck in my craw for a few weeks…

So the organizers of the annual Brady Street Festival are considering moving the date of their long-running shindig in order to avoid an extremely, EXTREMELY busy weekend. The fest typically takes place on the last Saturday of July; this year, that Saturday (July 27) will be smack-dab in the middle of not only familiar returning events—German Fest, the MKE Air & Water Show, the Riverwest 24—but the now-annual Harley-Davidson Homecoming Festival. It’s that last lakeside blowout that has the Brady Street Fest folks concerned.

“If we move, it will be because of Harley Fest,” Brady Street Improvement District Executive Director Michael Sander told the Milwaukee Journal Sentinel two weeks ago. “My big concern is to make a decision that is beneficial to all the businesses on Brady. Does that mean moving Brady Street Fest and participating in Harley Fest? That’s a possibility.”

I don’t know about you, Tyler, but the fact that an established and wildly popular event like Brady Street Festival is considering a date change is WILD to me. So here’s my (only slightly hyperbolic) question: Milwaukee summers have always been packed, but are they getting TOO packed? Have we reached a tipping point? Are there simply TOO MANY THINGS happening in the summer for Milwaukee to handle? And lord almighty, don’t even get me started on an earlier Festa Italiana (May 31 – June 2), three Summerfest weekends (June 20-22; June 27-29; July 4-6), and the Republican National Convention (July 15-18)…

Tyler Maas: Even though Milwaukee is called the “City of Festivals” for good reason, I do agree that it seems as if there are more large-scale events vying for prime placement on the entertainment calendar lately. While festivals, block parties, and other ambitious happenings aren’t unheard of in fall and winter, the vast majority of fests and fest-like happenings occur between the very end of spring and the entirety of summer. That crowded landscape in a relatively small window forces lots of overlap and, in recent years especially, frequently leaves residents with difficult decisions about which one or two things to commit to doing on a weekend day where there are—no exaggeration—as many as seven or eight big events happening at the same time.

For the most part, I view a summer season that’s packed with celebrations, live entertainment, and outdoor-focused community fun to be a good thing. I’ve only lived in Milwaukee for 15 years and the fact we’re even talking about a “tipping point” being in consideration when it comes to things like the abundance of festivals (along with things like venues, breweries, and “food halls”) is astounding to me. It seems a world away from NEEDING the Summer Soulstice lineup to hit and relying on a few solid Summerfest headliners to ensure a quality summer. Now, the onus falls squarely on individual festivals and their organizers to make sure their event is successful because the general public has ample alternatives to consider. Increased options are good, but that also brings increased competition…especially in a mid-sized metro city like Milwaukee.

Events changing dates isn’t entirely unique. For example, over the decade we’ve been doing this site, sometimes Locust Street Festival happened the first Sunday in June. Other times, it would happen the second Sunday. That inconsistency would cause occasional overlaps with PrideFest (which has since moved to a Thursday to Saturday model in order to avoid getting in the way of the city’s massive Pride Parade—no longer making Locust Street overlap possible). Adjustments were made and life went on. And if Brady Street Festival decides to move in order to avoid some events, it will inevitably overlap with other things. That’s summer in Milwaukee for you! However, what I am bothered by is Summerfest taking three weekends these days instead of its usual two and, more so, the two events that have brazenly wedged themselves into the heart of festival season this year—only further complicating things either directly or through a domino effect.

Despite happening during the week, the RNC is going to add to the seasonal chaos and require a ton of the city’s resources in regard to police presence and other infrastructure needed to adequately execute an event that will thrust Milwaukee onto a worldwide stage. Then days later, the apparently now annual for some reason H-D Homecoming Festival will bring bikers—as well as non-biker fans of Jelly Roll and Red Hot Chili Peppers—to the actual festival at Veterans Park and other enclaves of the city (that also will require contracted police and/or security presence and road closures). I don’t think Milwaukee is at a tipping point of too many festivals in general, but cramming these citywide undertakings into the mix makes what I think would otherwise be a manageable and downright encouraging collection of “big” Milwaukee summer events exponentially more difficult to handle.

I’ve gone on long enough. (Sorry!) Matt, do you have any thoughts as to how this suddenly crowded festival calendar can be addressed, organized, and better navigated? Personally, I’m thinking we just get through this inordinately busy summer somehow (even if unprecedented date changes are needed), then—with the knowledge the RNC will be gone and the hope H-D Homecoming’s footprint will recede—proceed as usual in 2025.

Matt: How to best navigate the upcoming super-sized summer weekends? It seems to me there are two options: tamp down any feelings of FOMO and pick one thing per day/weekend; or succumb to decision paralysis and head out of town and go camping or something. There’s a big, beautiful state out there! If there are simply too many things happening at once in Milwaukee, get the hell out of Milwaukee! (I know plenty of folks who plan to use this strategy during the RNC.)

You’re right that this certainly isn’t the first time an event or events have changed dates to accommodate something else, but it really seems like it’s “every event/festival for itself” these days. Remember when smaller clubs and venues would completely shut down during Summerfest? (Some still do.) That’s a dicier proposition now with the Big Gig taking up three weekends instead of two. The days of the little guys/gals making room for an everything-to-everyone blowout like Summerfest may be gone. Music and entertainment are incredibly fragmented and niche these days, so why not festival entertainment? (Summerfest’s dogged insistence on still being everything to everyone in an increasingly fragmented world is a topic for another time…)

Maybe in the end we simply have to chalk this up as a “nice problem to have.” Milwaukee has a glut of things to do in the summer! Boo-hoo! I don’t know if summer 2025 will be that much calmer (the Harley fest seems like it’s here to stay), but if summer 2024 is a complete shit show, so be it. BRING IT ON.

Tyler: I share your “nice problem to have” sentiment wholeheartedly. And I also look back wistfully at a time in the not-so-distant past where larger festivals either worked together to avoid overlap or, more often, at least made any semblance of an effort to stay out of each other’s way. However, there are a finite number of warm weather weekends here in the City of Festivals and there’s more going on than ever before. It’s going to be a mess and every large-scale happening this year will endure for the long haul. Factors like organization (and staffing/volunteers), consumer preferences, and random luck in the form of good weather will each play a part in dictating what the future holds. But for now, I’ll join your cry to BRING. IT. ON.

Oh, and by the way, I have a thing July 15-18, so I’m going to be out of town. Hope you can hold things down solo during that span, partner!

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Stuff We Missed: Brady Street Fest may change date because this summer is gonna be PACKED