30+ Fall Festivals, Fairs and Markets You Won’t Want to Miss

Welcome fall to Milwaukee with these events.

BY BRIAN ROSENZWEIG AND ALLISON PEOPLES

SUMMERFEST PRETTY PERFECTLY bookended the actual summer season this year, but that doesn’t mean Milwaukee’s festival fun stops now. From free events that showcase Milwaukee’s vibrant arts scene to a catalog of harvest festivals and Oktoberfests to last all season, Milwaukee knows how to turn up when the temperatures cool down.

September

1. Pumpkin Fest

THROUGH OCT. 31 | BASSES’S TASTE OF COUNTRY, COLGATE

A corn maze, racing pigs, a petting zoo and a candy cannon are just a few highlights.

2. The Elegant Farmer’s Autumn Harvest Festival

SATURDAYS AND SUNDAYS THROUGH OCT. 24 | 1545 MAIN ST., MUKWANAGO

Running every weekend throughout the fall season, Autumn Harvest Festival is every bit of traditional fall activities and nostalgia baked into one event, with hayrides, apple picking, pumpkin patches, corn mazes and everything in between. And, as a specialty farm and cafe, let The Elegant Farmer treat you to such delights as fresh cider, pies, apple cider donuts and pulled pork sandwiches.

3. Harvest Fair

SEPT. 24-26 | WISCONSIN STATE FAIR PARK

Celebrating its 28th year, Harvest Fair is a weekend-long fall tradition presented by Wisconsin State Fair Park that brings together all things fall. From local food and produce vendors to live music to carnival rides and pony shows (what else do you expect from the State Fair Park?), the festival is an invitation to take part in the abundant “harvest” of Milwaukee, and all the season brings.

4. Milwaukee Paranormal Conference

SEPT. 24-26 | MKE PARACON

All things spooky can be checked off your list this year at the paranormal conference with events like, Yoga in the Cemetary, a Ghost Story Open Mic, ghost walks around the city, and even the worlds largest ghost hunt! Bring some friends and may you have a ghoul-friendly time.

5. Fall Jefferson Swap Meet & Car Show

SEPT. 24-26 | JEFFERSON COUNTY FAIRGROUNDS

One of the largest car shows in the midwest, this event hosted by Madison Classics offers an opportunity to swap car parts, showcase vintage vehicles and get to know the local car-enthusiast community.

 

 

6. SWARMM Milwaukee Oktoberfest

SEPT. 24-26 | WAR MEMORIAL CENTER

Beer and German food, music from the likes of “Polka Floyd,” a beauty AND wiener dog pageant; what more could you ask for? Answer: pull up early on Friday for the opening of the first keg, and enjoy some free beer. Oh, and proceeds benefit the War Memorial Center. That’s something to raise a pint to.

7. Maker Faire

SEPT. 24-26 | MILWAUKEE SCHOOL OF ENGINEERING

“Part science fair, part county fair,” Maker Faire brings together local engineers, scientists and creatives alike to showcase their work, and be inspired by others. Anyone from industry professionals to amateur backyard scientists can participate, as a chance to showcase their talents, ask questions and collaborate.

Photo Courtesy of ‘Maker Faire Milwaukee’

8. Hay Days & Oktoberfest Biergarden

SEPT. 25 | DOWNTOWN GREENDALE

Enjoy a whole day filled with fall fun for the entire family. Kick-off the day by strolling through the Downtown Market, then head over for festive face paint, pumpkin bowling and a silly charicature portriat! Wind down at the end of this fun-filled day with some tunes from The Whiskey Belles while you sip on some Explorium beer.

9. Equinox Music Festival

SEPT. 25 | THE BREWERY DISTRICT

Get bundled up for and incredible night out dedicated to performances by local musicians. Nineteen Milwaukee artists will take the stage at this outdoor music fest for you and your crew to enjoy the city’s most curated sounds, sights, and tastes with several local venus to grab drinks from.

10. BashtoberFest Fest

SEPT. 25 | VENNTURE BREWING CO.

“Hoist a stein! Don a cap! Order a beer and tip it back!”, Vennture Brewing Co. is gearing up for a sure-to-join shindig! Grab yourself an Oktoberfest beer and compete in a game of Stein Hoisting or Hammerschlagen, or just come together with friends for some traditional Polka dancing.

11. Fromm Petfest

SEPT. 25 | HENRY MAIER FESTIVAL PARK

A family-friendly event where you never have to ask, “can I bring my dog/cat?,” Fromm Petfest is all about our four-legged friends. From open agility courses to main stage presentations, alongside plenty of food and music for human enjoyment, Petfest turns Henry Maier park into an animal utopia for a full day of furry-loving fun.

12. Third Space 5th Anniversary Party

SEPT. 25 | THIRD SPACE BREWING CO.

Containing your excitement for sustaining the community can be hard, but not at this celebration! That’s what it’s all about, so join the Third Space Brewing Co. for their 5th year since opening with a zero-waste party featuring live music, food trucks, sustainability education, and of course, unique beers to try!

13. Germantown Historical Society Oktoberfest

SEPT. 25-26 | DHEINSVILLE HISTORICAL PARK

With authentic food, beer, music, dancing, and a “dachshund dash,” there’s a reason this annual Oktoberfest from Germantown’s Historical Society has been going on 13 years strong.

14. Doors Open Milwaukee

SEPT. 25-26 (IN PERSON), SEPT. 25-OCT. 3 (VIRTUAL) | MILWAUKEE

Create your own specially curated itinerary with over 70 sites around Milwaukee to see. This event allows you to explore the beautiful neighborhoods, architecture and history the city has to offer with in-person and virtual tours, plus a newly added water themed scavenger hunt.

Milwaukee Symphony Orchestra’s Bradley Symphony Center; Photo via Doors Open Milwaukee

October

15. Love, Milwaukee Block Party

OCT. 1 | LINCOLN WAREHOUSE

Be one of the first people to ever try the the beers and kombucha that will make up the “most diverse six pack in Milwaukee’s history.” And what could make things better? Answer: Local beer and tasty food! Local breweries will have drinks to cleanse your pallet as you indulge in food truck dishes and late-night pizza!

16. The Hollow at Phantom Lake

OCT. 1-24 | PHANTOM LAKE YMCA CAMP, MUKWONAGO

This summer campground transforms itself into a fall haven with thousands of hand-carved illuminated Jack O’lanterns lighting the way. Check thehollowwi.com for specific dates and times.

17. Free Day of Theater

OCT. 2 | MILWAUKEE REPERTORY THEATER

A great chance to see the theatrical talent Milwaukee has to offer, this event hosted by the Milwaukee Repertory Theater showcases with 10, 60-minute performances by the Quadracci Powerhouse Theater and Stiemke Studio. Ranging from concerts to dance workshops to teen performance showcases, the Free Day of Theater is a great sample of Milwaukee’s rich arts scene.

Photo by JPM Photography

18. The Lowdown

OCT. 2 | INDEED BREWING COMPANY

For it’s 3rd annual street fest, the Indeed Brewing Company will go all out for the celebration with never-before-tried beers, fresh drinks straight from the fermenter, food truck eats and live art by Jeff Redmon.

19. Cedarburg Oktoberfest

OCT. 2-3 | DOWNTOWN CEDARBURG

The German’s know how to throw a great party! Down to the delicious foods, tasty beers and an array of fun activities. The Sauerkraut Eating Contest and the German Spelling Bee from Ault to Zither (A-Z) are sure to make for a good belly laugh with your friends.

20. Milwaukee Lakefront Marathon

OCT. 3 | HENRY MAIER FESTIVAL PARK

Celebrating its 40th year, this iconic marathon brings the community together for a trek up Milwaukee’s lakefront, now with a two-person relay option, a kid’s run, and of course, a post-marathon celebration on the Summerfest grounds, with food, beer and music.

Lakefront Marathon; photo courtesy of Dave O’Brien

21. Brady Street’s Pet Parade

OCT. 3 | BRADY STREET

What’s better than a pet? Answer: Pets in costumes! You’ll be seeing lots of the cutest furry critters come to show off their costumes, tail wagging, and tricks during the celebration! After the parade passes through, the party continues with live music by Trapper Schoepp.

22. Milwaukee Comedyfest

OCT. 3-10 | THE LAUGHING TAP

Billed as the largest multi-day comedy event in the state of Wisconsin, Comedyfest has been bringing together stand-up, sketch comedy and improv acts from across the country for the past 15 years, with alumni who have gone on to work for the likes of Conan, Comedy Central, Netflix, and SNL. And, being hosted at the Laughing Tap, you’re always in the company of good beer and good people.

23. Pridetoberfest

OCT. 8-9 | HENRY MAIER FESTIVAL PARK

Pride doesn’t end in June! After the cancelation of Pridefest for a second year due to COVID complications, Pride Milwaukee announced Pridetoberfest, a smaller-scale event that will still bring together all the same community, joy and pride as the summer event. With food and drinks from local vendors, plenty of music, and dancing, this won’t be one to miss.

Photo by Visit Milwaukee

24. Beet Street Fall Festival

OCT. 9 | CACTUS CLUB

If you like getting groovy, rocking out or just enjoy a good time, then this street festival is exactly where you need to be this October. With their 5th annual festival, the Cactus Club is bringing out the big guns with performances from Ric Wilson, Frankie & The Witch Fingers and more.

25. Crusherfest

OCT. 9-10 | 1101 MILWAUKEE AVE.

A mashed up day full of competition, beer, music and more. If you think you have what it takes to become the next Mr Saloon then join the fun and take your chances with the best during their 5 rounds of crusher competition.

26. Whitewater Storytelling Festival

OCT. 15-16 | CRAVATH LAKEFRONT PARK

The perfect event for anyone who loves a good story, the Whitewater Storytelling Festival is a weekend-long event with storytelling sessions for all ages, workshops, local author showcases and plenty of art exhibits. Immerse yourself in the many ways stories are told, and maybe even come back with some stories of your own.

27. Bayshore BOOgie Bash and Costume Contest

OCT. 22 FROM 5-7 P.M. | THE YARD AT BAYSHORE

This free event will have a live D.J., Halloween displays and family-friendly activities. The costume contest is an opportunity for children to win prizes. There will be a hay maze and light show too.

28. West Bend Community Drive-Thru Pumpkin Patch

OCT. 23 | VETERANS AVENUE, DOWNTOWN WEST BEND

Like Christmas in October, drive through the West Bend neighborhood for a stunning display of community-made jack-o-lanterns, alongside interactive spooky characters and ambient music to set the mood.

29. Halloween Barktacular

OCT. 27 | 301 COMMERCE ST., WAUKESHA

It’s hard enough for our four-legged friends on Halloween, with incessant doorbell rings, bowls full of off-limit chocolates, and the entire neighborhood going on a walk without them. Why not treat them to something for themselves? Halloween Barktacular, hosted by Think Pawsitive in Waukesha, features plenty of games, treats for dogs and humans, a canine costume contest, and plenty of chances to win prizes.

30. Dia De Los Muertos Day of the Dead Festival

OCT. 30 | FOREST HOME CEMETARY

A family-friendly event for all folks to come and celebrate the traditions of the Dia de los Muertos and admire the grounds of Forest Home Cemetery and Arboretum. To kick-off the event, there will be a 5K run/walk through the cemetery, and after you can enjoy food trucks, local vendors, arts and crafts, music and more.

A calavera is a representation of a human skull. The term is most often applied to decorative or edible skulls made (usually by hand) from either sugar (called Alfeñiques) or clay which are used in the Mexican celebration of the Day of the Dead (Día de los Muertos) and the Roman Catholic holiday All Souls' Day.
Photo via Getty Images

31. Halloween Parade and Costume Contest

OCT. 31 | DOWNTOWN GREENDALE

End your spooky October celebrations with a Halloween-themed parade and don’t forget to where your best costume for a chance to win the contest! Close the night with many tricks and treats to last you until next year.

November

32. The Great Hartford Craft Exposition

NOV. 13 | HARTFORD UNION HIGH SCHOOL

A perfect event for the turn of the seasons, this expo in its 37th year brings together 100 local exhibitors for lively displays of arts and crafts.

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