12 Things to Do in Milwaukee This Weekend: Oct. 21-23

Originally Published on Milwaukee Magazine 10/20/22

Halloween activities are heating up in the city. Haunted city tours, scary bloody mary walks and classic horror cinema await you this weekend. 

The Shining

ALL WEEKEND | TIMES CINEMA 

This week, Times Cinema kicked off their 7th annual “Shocktoberfest” film festival. This weekend’s installment is the horror classic, “The Shining.” Based on Stephen King’s best selling book of the same name, Stanley Kubrick creates a chilling demonstration of malicious manipulation and fear-- a must-see for fans of the macabre. 

Jon Lovitz

ALL WEEKEND | MILWAUKEE IMPROV

Saturday Night Live alum Jon Lovitz is coming to Milwaukee for a weekend of local laughs. Lovitz has starred in a variety of classic nineties and early aughts comedies including Coneheads, Rat Race, The Stepford Wives, Little Nicky and many more. Check out one of his four Milwaukee shows before he heads back to Las Vegas for his residency at the Laugh Factory. 

Exhibit Opening: The World's Lung with Catalina Bayona 

FRIDAY FROM 5 P.M. - 9 P.M. | ARTS @ LARGE 

Friday night is the opening of “The World’s Lung,” an art installation by Colombian artist Catalina Bayona.  Her installation shines a light on the vibrancy of the Amazon, the “lungs of the world.” Bayona tells stories about the natural world and humanity through her multi-media installation, inviting viewers to expand their understanding of the human condition. 

Gremlins

FRIDAY AT 6:30 P.M. | MILKY WAY DRIVE-IN

Remember the rules: no bright light, no water and no food after midnight, and you may just survive Friday’s showing of 1984’s “Gremlins” at the Milky Way Drive-In. Pick up some popcorn and drinks and enjoy the black comedy from the comfort (and safety!) of your own vehicle. 

Life With The Afterlife: A Supernatural Evening With Ghost Hunter Amy Bruni

FRIDAY AT 7:30 | WILSON THEATER AT VOGEL HALL

Paranormal investigator Amy Bruni is coming down to the Marcus Performing Arts Center to share stories of her chilling experiences at America’s most haunted locations. Enjoy a night learning about thrilling paranormal encounters just in time to prep you for spooky season. 

Gallery Night 

FRIDAY AND SATURDAY | HISTORIC THIRD WARD, WALKER’S POINT, EAST TOWN

Gallery Night is back with over 30 locations of new exhibits to enjoy. Milwaukee's original gallery hop is a great opportunity to check out local and regional artists while exploring some of the city’s most creative neighborhoods. Want to make the most of your experience? Use their website’s itinerary planning tool to create the easiest route to the galleries you want to visit. 

Pumpkin Pavilion 2022

FRIDAY AND SATURDAY | HUMBOLDT PARK

Bring the family down to Humboldt Park on Friday and Saturday to partake in this year’s Pumpkin Pavilion. Walk through hundreds of carved pumpkins on display while enjoying live bands, magic and more. Over 2,000 Milwaukeeans are expected to come down to Humboldt Park to embrace the fun of Halloween. 

Spirits of the Silent City: "Unfinished Business"

FRIDAY AND SATURDAY | FOREST HOME CEMETERY

Spirits of the Silent City is an immersive after-dark experience at Milwaukee’s oldest and largest cemetery. This weekend, some of Forest Home Cemetery's most notable residents including Dr. Laura Ross Wolcott, Ezekiel Gillespie and Maude Miriam Hicks Wright, will slip through the veil separating the living and the dead to settle some unfinished business. 

Scary Bloody Mary Walk 2022

SATURDAY AT NOON | CEDARBURG 

Twelve bars in Cedarburg are competing for the Best Bloody Mary award. This weekend, participants can visit their choice of five contesting bars, do some sampling, then vote for their favorites. Costumes are not required, but encouraged-- there are several costume-related awards participants can win.


Gargoyles, Grotesques & Dragons

SATURDAY 2 P.M. - 4 P.M. | HISTORIC MILWAUKEE, INC. 

The world of monsters, demons and strange beasts comes to life this weekend during Historic Milwaukee, Inc’s tour of the gargoyles, grotesques and dragons that adorn many of downton Milwaukee’s most famous buildings. Pre-registration is required and tour guides suggest bringing a pair of binoculars. 


Sweet Baby James: A James Taylor Tribute

SATURDAY AT 7:30 P.M. | SKYLIGHT MUSIC THEATER 

American singer-songwriter James Taylor has created decades worth of memorable songs. This weekend, musician Bill Griese aka “Sweet Baby James” is coming to the Skylight Theater to perform some of Taylor’s most famous tunes. Ticket prices start at $25 for this one-night music homage.

Día de los Muertos

SUNDAY 10 A.M. - 3 P.M. | MILWAUKEE ART MUSEUM 

This Sunday, the Milwaukee Art Museum opens its doors to families looking to celebrate the culture and sounds of Día de los Muertos. Visitors can enjoy live music, hands-on activities, children’s crafts and more while they learn about the importance of the holiday and special celebratory traditions.

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