What’s the Best Milwaukee Holiday Tradition? | Milwaukee Magazine

Ask MilMag: What’s the Best Milwaukee Halloween Tradition?

In this series, Milwaukee Magazine staffers answer questions about the city, share cherished memories, give unsolicited advice and crack the occasional dumb joke.

1. Trick-or-Treat in Jackson Park

LIZ LINTONEN, EDITORIAL INTERN

My favorite Halloween tradition in Milwaukee is the evening trick-or-treating in the Jackson Park neighborhood. The neighborhood is unparalleled in its decorating, festive energy and spooky holiday environment. It was a staple of my childhood, and I am of the firm belief that it might be the best trick-or-treating in all of Milwaukee. 

2. Tosa East Towne’s Halloween Block Party

CHRIS DROSNER, EXECUTIVE EDITOR

As a resident of the Tosa East Towne neighborhood, this is an easy one for me. Every Saturday before Halloween (Oct. 28 this year), the neighborhood holds what’s essentially a Halloween-themed block party spanning dozens of square blocks, with most of the action bounded by 69th Street, Lefeber Avenue, Center Street and North Avenue. Expect firepits blazing, decorations to the max, trick-or-treating for young ones and Jell-O shots and the like for older revelers. 6:30-8:30 p.m. Saturday, Tosa East Towne 

A costumed resident pours beer samples for grown-up trick-or-treaters at the 2021 Tosa East Town trick-or-treat event; Photo by Jodi Drosner

It’s time to pick your Milwaukee favorites for the year!

 

3. Dress Up and Go Out

BRIANNA SCHUBERT, ASSOCIATE DIGITAL EDITOR

This isn’t exactly specific to Milwaukee, but I love just simply dressing up and going out for Halloween weekend every year. I usually change up where I go each year, and this year is no different. I’m dressing up as a fairy and going to Rocky Horror Picture Show at Oriental Theatre on Saturday night. I haven’t been to the show before, but I’ve heard great things and am very excited to check it out. Oh yeah, and I’ll also be going to Spooky Square Dancing at Third Space tonight – which has square dancing and a costume contest! 

4. 1840 Brewing Tap Takeover

CHRIS DROSNER, EXECUTIVE EDITOR

I also have to put in a plug for the 1840 Brewing tap takeover at Ray’s Growler Gallery. The beers all have Halloween themes (think “Michael Milders” English mild) and my friend DJ Corpse Reviver (I know, the company I keep…) curating zombie movies and leading a themed trivia as well. 4-10 p.m. Saturday, 8930 W. North Ave., Wauwatosa 

5. Handing Out Candy in the North Shore 

ANN CHRISTENSON, DINING EDITOR

My tradition on trick-or-treat Sunday is to go to my brother’s place and help pass out candy. He lives in a neighborhood that draws a healthy crowd of kids, and there’s a neighbor who makes it more fun by dressing in an ape suit and making warm spiced cider. If my brother caps off the afternoon by making his famous chili, that’s just the icing.