Our Favorite Milwaukee Fall Festivals

Milwaukee Fall Festivals

Fall is so beautiful in Wisconsin, the colors pop making our city come alive! And guess what? Here in the 414, 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 all kinds of fun 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 22 – 24

Wisconsin State Fair Harvest FairA Bounty of Fun for Everyone! Save the Date for Harvest Fair presented by Meijer, September 22-24, 2016. FREE Admission.

The dates and times for Harvest Fair are:
-Friday, Sept. 22: 5pm – 11pm
-Saturday, Sept. 23: 9am – 11pm
-Sunday, Sept. 24: 9am – 5pm

Fun activities for kids of all ages include pumpkin bowling, scarecrow making, decorate your own cookie, Great Lakes Timber Show, amusement rides 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 flowers, food and more! Pick up pumpkins at the Pumpkin Patch, and don’t forget your Elegant Farmer pies! 

Here are some of our favorite Fall Festivals in Milwaukee ::


Big Gig BBQ –Milwaukee (Summerfest Grounds), September 3: Back for a second year, the folks from Summerfest pair BBQ and entertainment for a one-day experience my husband is already drooling over. Fourteen different regional and local cookers will be on hand, and I’m really looking forward to the cooking demonstrations. Family fun picnic games and a celebrity bacon eating contest round out the event. (Oh, and did I mention that both admission AND parking are free??)

Indian Summer Festival — Milwaukee (Summerfest Grounds), September 8-10: Indian Summer Inc. was formed for the purpose of organizing and presenting an American Indian ethnic festival. The mission is to educate, preserve and promote American Indian cultures; showcase the diversity that exists within tribal cultures; provide economic opportunities to our people and strengthen communication and understanding.

Taste of Mequon — Mequon, September 9: This family event has everything from children’s activities to artists and music. 

Tomato Romp Fest — Milwaukee East Side, September 9: A day of throwing tomatoes (over 8,000  pounds!) and Bloody Mary tastings. There’s also a costume contest. All proceeds go to Riverwest Food Pantry

Frank Mots Int’l Kite Festival — Milwaukee (Veteran’s Park), September 9-10: Fly your kites high with the rest of Milwaukee on the special day by the lakefront! 

Rock the Green — Milwaukee (Reed Street Venue), September 9: Rock the Green is a non-profit organization with a green mission. The core of this mission is the production of a large scale festival that showcases zero waste best practices and world class music. Kids under 10 are FREE.

Raspberry Festival — Jackson (Jackson Historical Society Museum & Grounds), September 10: Come to an old-fashioned family ice cream social with Amish-made raspberry pie and Honey Acres ice cream! Friendly for the entire family!

Bay View Bash — Bay View, (KK between Potter and Clement) September 16: A community festival of food, art, music, crafts, books and community organizations. Striving to be a zero waste festival! 

Sausage Fest — Bay View (Café Centraal), September 16: $10 gets you all-you-can-eat sausage, and all net proceeds benefit Camp American Legion.

Wine & Harvest Festival — Cedarburg (Festivals of Cedarburg), September 16-17: Spend a sweet, end-of-summer weekend in the country in Historic Cedarburg during the 45th 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 22-24: 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!

Apple Harvest Festival — Waukesha (Retzer Nature Center), September 23: Come for apple pies, apple crisp, and caramel apples; stay for the nature and the family memories. 

Fromm Petfest — Milwaukee (Summerfest Grounds), September 23: 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.

Apple Harvest Festival — Waukesha, September 23. It’s hard to beat $5 admission FOR THE 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.


Milwaukee Oktoberfest—Milwaukee (Pere Marquette Park) September 29-October 1, October 6-8. Milwaukee Oktoberfest has free entry for everyone, and benefits Hunger Task Force, Inc. 

Oktoberfest 2017 — Cedarburg (Festivals of Cedarburg), October 8-9: A perfect weekend in October at Oktoberfest includes authentic German music, German cuisine and beer, polka dancing, glockenspiel shows, fun contests, art and more!

Dia de los Muertos Milwaukee Festival — Walker’s Point (Walker Square Park), October 28: The Mission/Misión is to bring communities within Milwaukee together through El Dia de los Muertos/Day of the Dead Parade Project. Its purpose is to preserve, promote, and share the traditions and significance of the Day of the Dead by inviting the community to participate in this joyful event and in the process promote cultural awareness, understanding & peace. 


Trainfest — Milwaukee (Wisconsin State Fair Grounds), November 11-12: 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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