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!

Although this year’s Fall will look and feel very different due to Covid-19, there are still many events open for us to enjoy!

The team at Milwaukee Mom is working hard to remain your go-to spot for parenting resources in the Greater Milwaukee Area. While we will do our best to be as up-to-date as possible, please be aware that we are still dealing with changes related to the COVID-19 Pandemic. Please consult your local public health authority for social distancing recommendations and call ahead to confirm the hours and offerings of any business or organization listed.

Our Favorite Fall Festivals in Milwaukee:


Glendale Oktoberfest – Glendale (Heidelberg Park)September 2 – October 3.

This event is the oldest and most authentic Bavarian Oktoberfest in the Midwest…just north of Milwaukee in Glendale, Wisconsin. Oktoberfest, modeled just like the one held in Munich, Germany. Continuous entertainment includes traditional German brass bands, Schuhplatter folk dancing, singing, yodeling, sing-alongs, traditional German eats such as spanferkel and rollbraten, German beer, and dancing for everyone. This is a kid-friendly festival with children’s carnival games. Held five-weekends in the Fall! Free admission!

TosaFest — Wauwatosa. September 10 – 11.
A fun family festival that is 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 lineup of local bands for entertainment.

Taste of Mequon — Mequon. September 11.
A fun family festival that’s 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 lineup of local bands for entertainment.

Harvest Fair — Milwaukee (Wisconsin State Fair Grounds): September 24-26.

A bounty of fun for everyone. Free Admission. 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!

Frank Mots Int’l Kite Festival — Milwaukee (Veteran’s Park): September 11-12.

Fly your kites high with the rest of Milwaukee on a special day by the lakefront!

Apple Harvest Festival — Waukesha (Retzer Nature Center): September 18.
Come for apple pies, apple crisp, and caramel apples; stay for nature and the family memories. $10 admission (cash only) for an entire car. Add in arts and crafts, children’s activities, scarecrow lane with a scavenger hunt, passport expeditions on the Discovery Trail, a craft fair, planetarium shows, self-guided nature hikes, and you’ve got a real winner

Wine & Harvest Festival — Cedarburg (Festivals of Cedarburg): September 18 – 19.
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.

Fromm Petfest — Milwaukee (Henry Maier Festival Park): September 25. 
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. An added bonus for this fall festival? Admission and parking are free for the whole family. Bring your pets!

Oktoberfest Milwaukee — Milwaukee (War Memorial Center): September 24 -26.
Milwaukee’s 11th annual Oktoberfest is a weekend full of German beer, food, music, and more! Some of the weekend’s German event includes a Weiner dog beauty pageant, stein hoisting competition, Miss Oktoberfest Pageant, and, of course, live polka music all weekend. The event is free to the public.


Oktoberfest— Cedarburg (Festivals of Cedarburg): October 2 – 3.
A perfect weekend in October at Oktoberfest includes authentic German music, German cuisine, beer, polka dancing, glockenspiel shows, fun contests, art, and more!

Fall Festivals Canceled for 2021

Big Gig BBQ — Milwaukee (Summerfest Grounds): 2021 event canceled. 
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.

Bay View Bash — Bay View, (KK between Potter and Clement): 2021 event canceled.
A community festival of food, art, music, crafts, books, and community organizations. Striving to be a zero-waste festival!.

Trainfest — Milwaukee (Wisconsin State Fair Grounds): 2021 event canceled.
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 are so many opportunities for both kids and adults to be more hands-on than ever before!

We are as bummed as you are that some festivals will not get to happen, but we can still have fun this fall in socially distant ways. Check out some of our other guides here:

15 Fall Road Trips for Milwaukee Families

Our Favorite Milwaukee Area Apple Orchards

Our Favorite Milwaukee Area Pumpkin Farms

2021 Farms, Pumpkin Patches, Orchards, and Corn Mazes

Which fall festival are YOU most looking forward to or are most disappointed won’t be returning this year? Did we leave an awesome one out? Sound off in the comments!

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Megz is a Midwest transplant from the Central Coast of CA. She lives in Muskego with her husband and their 4 young girls. Prior to being a SAHM, she was a nurse for 6 years. She’s a black-coffee drinker, shampoo-dealer, introvert, homebody, and green/ healthy living enthusiast, but above all things, she’s a true believer in faith. Her days are filled with gardening (all year long), caring for her family, managing her businesses, and loving on all her people. Radiate positivity and make her laugh… she’ll be your friend forever. The 2 things she loves most about living in WI is experiencing all 4 seasons and being around the friendliest people. The hardest thing? Probably being lactose intolerant and living in dairy land.


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