The Best Things to Do in Milwaukee This October

Pair fairs with scares this month in Milwaukee.



 
 
1.

Milwaukee Comedy Festival

OCT. 2-9 | MULTIPLE VENUES | $

Comedians from around the country are stopping by Cream City for this weeklong event. This year’s headliner is Laurie Kilmartin, a quick-witted comedian with credits on “Conan” and Comedy Central and a book called Dead People Suck. Leave the tomatoes at home.

The Laughing Tap; Photo by Brianna Schubert



 
 
2.

Holy Hill Art & Farm Market

OCT. 8-9 | $

Consider this shopping adventure a treasure hunt for art, vintage finds and locally made goods. Farmers will be there with produce and baked goods, and there will be live music, too. Be sure to spend some time soaking in the fall colors, as the Holy Hill area is one of the best spots around to enjoy the changing leaves.

Holy Hill; Photo by Visit Milwaukee


 

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3.

Empty Bowls

OCT. 9 | $

The concept of this Deer District event, where you buy a handmade bowl and fill it with free soup samples, is a reminder that someone’s bowl is always empty. Funds raised support food-insecure families via Friedens Community Ministries.

Courtesy of Milwaukee Empty Bowls via milwaukeeemptybowls.org



 
 
4.

Sweetest Day Dinner on the East Troy Railroad

OCT. 15 | $

Sometimes overshadowed by its showy February cousin, Sweetest Day is an easy “holiday” to overlook, but this special train ride can make it memorable. Enjoy a three-course meal, all while chugging through some stunning rural Wisconsin fall foliage.

Photo courtesy of the East Troy Railroad Museum



 
 
5.

Boo at the Zoo

OCT. 20-23 | $

This trick-or-treat trail through the zoo features a bagful of fun for the little kiddos, including an animal-themed “Jack’s Path” full of hand-carved pumpkins and decorations recreating scenes from classic Halloween movies. The outdoor animals won’t be available for viewing, but fear not – there’ll be a presentation on creatures of the night, and you can slither on into the aquatic and reptile center.

Photo by Evan Watters



 
 
6.

Pumpkin Chuckin’

OCT. 29 | GREENDALE HIGH SCHOOL

Prepare for airborne pumpkins shot out of a … catapult! For those who love to watch pumpkin guts explode all over asphalt, this is a must-see event.

Photo by Getty Images



 
 
7.

Haunted Houses

$

Not for the faint of heart, local haunted houses can pack some serious scares. The Hill Has Eyes is nearby in Franklin, but also consider the short trip to Mount Pleasant for the Abandoned Haunted House Complex if you’re looking for true terror.

Photo via the Hill Has Eyes Facebook


 

This story is part of Milwaukee Magazine’s October issue.

Find it on newsstands or buy a copy at milwaukeemag.com/shop

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Allison Garcia is the Digital Editor for Milwaukee Magazine.