Our Favorite Milwaukee Fall Festivals


Fall is so beautiful in Wisconsin, the colors pop making our city come alive! And guess what? Here in Milwaukee, we don’t let the cooler temps keep us from throwing a party or two so the festivals don’t stop just because summer ends!

This guide to Milwaukee area fall festivals includes all kinds of fall family fun is brought to you by our friends from the Wisconsin State Fair, featuring Harvest Fair

Harvest Fair at Wisconsin State Fair Park :: September 27 – 29

A Bounty of Fun for Everyone! Save the Date for Harvest Fair presented by Meijer, September 27-29, 2019 FREE Admission.

Harvest Fest 2019The dates and times for Harvest Fair are:

  • Friday, Sept. 27: 5 pm – 11 pm
  • Saturday, Sept. 28: 9 am – 11 pm
  • Sunday, Sept. 29: 9 am – 5 pm

Fun activities for kids of all ages include pumpkin bowling, scarecrow making, decorate your own cookie, Great Lakes Timber Show, amusement rides, the famous State Fair giant slide and more! Come hungry and ready to shop! Many of your favorite State Fair vendors are open during Harvest Fair, including The Micro, featuring over 50 craft beers. The Farmer’s Market features everything from Fall decorations to beautiful fall flowers, delicious fall food and more! Grab your kiddos and pick out your family pumpkins at the Pumpkin Patch, and don’t forget your Elegant Farmer pies! 

Our Favorite Fall Festivals in Milwaukee ::


Big Gig BBQ — Milwaukee (Summerfest Grounds), September 1
The fourth annual Big Gig BBQ is coming back to the Summerfest grounds and folks all over Milwaukee are drooling at the thought. Fifteen different regional and local cookers will be on hand, and I’m really looking forward to the cooking demonstrations. Family fun picnic games and an amateur BBQ Rib Competition. 

Glendale Oktoberfest — Glendale (Heidelberg Park) September 6 – October 5
Every Weekend: Fridays 5:00pm – 11:00pm, Saturdays 3:00pm – 12:00am. This is the oldest and most authentic Bavarian Oktoberfest in the Midwest!

TosaFest — Wauwatosa, September 6-7
A fun family festival full of music, games and fun for the whole family. The annual TosaFest includes a village of local food vendors and a kids area with bounce houses, a petting farm, a climbing wall and games!  The festival also includes a music line up of local bands for entertainment. 

Taste of Mequon — Mequon, September 7
This family event has everything from children’s activities to artists and music. 

Tomato Romp Fest — Milwaukee East Side, September 7
A day of throwing tomatoes (over 8,000  pounds!) and Bloody Mary tastings. There’s also a costume contest. All proceeds go to Feeding America.

Frank Mots Int’l Kite Festival — Milwaukee (Veteran’s Park), September 7-8
Fly your kites high with the rest of Milwaukee on the special day by the lakefront! 

Bay View Bash — Bay View, (KK between Potter and Clement) September 21
A community festival of food, art, music, crafts, books and community organizations. Striving to be a zero waste festival! 

Apple Harvest Festival — Waukesha (Retzer Nature Center), September 21
Come for apple pies, apple crisp, and caramel apples; stay for the nature and the family memories. $10 admission for an entire car. Add in an apple pie baking contest, children’s activities, a craft fair, planetarium shows, guided nature hikes, and horse-drawn wagon rides, and you’ve got a real winner.

Fromm Petfest — Milwaukee (Summerfest Grounds), September 21
Petfest will host a variety of pet-focused attractions and activities, including dock diving, agility and lure courses, main stage presentations featuring disc dogs and pet costume contests, a pet-themed marketplace, family-focused activities, music, food and more. Admission is free for the whole family.

Wine & Harvest Festival — Cedarburg (Festivals of Cedarburg), September 21-22
Spend a sweet, end-of-summer weekend in the country in Historic Cedarburg during the 47th Annual Wine & Harvest Festival. Both the abundance of Wisconsin’s homegrown produce and artisan food products plus the award-winning wines of Cedar Creek Winery are what initiated this free, family-oriented arts and crafts event.

Harvest Fair — Milwaukee (Wisconsin State Fair Grounds), September 27-29
Get the family together for a day at Harvest Fair! Enjoy fall-focused events, activities, live entertainment, competitions, scarecrow making and the much anticipated Pumpkin Bowling! FREE admission.


Oktoberfest Milwaukee — Milwaukee, October 4-6
Milwaukee’s 10th annual Oktoberfest, now located at the Fiserv Forum plaza, is a weekend full of German beer, food, music and more! Some of the weekend’s traditional German fun includes a Weiner dog race, brat eating contest, stein hoisting competition, and, of course, live polka music all weekend. The event is free to the public.  

Oktoberfest 2019 — Cedarburg (Festivals of Cedarburg), October 5-6
A perfect weekend in October at Oktoberfest includes authentic German music, German cuisine and beer, polka dancing, glockenspiel shows, fun contests, art and more!


Trainfest — Milwaukee (Wisconsin State Fair Grounds), November 9-10
Join the Fun at Trainfest, America’s largest operating model railroad show. Find the adventure this year when kids from 5 to 99 can run the trains at many of the railroads. There so many opportunities for both kids and adults to be more hands-on than ever before!

Which festival are YOU most looking forward to? Did we leave an awesome one out? Sound off in the comments!


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