Remember when the end of summer was also kinda-sorta the end of Milwaukee’s festival season? Those were simpler (and much more boring) times. Thankfully, the city’s already-bursting list of festivals, block parties, and other ambitious entertainment undertakings is extending well into autumn. As you get ready to have an awesome autumn, Here is Milwaukee Record’s fall festival guide.

September 23-25
Harvest Fair @ Wisconsin State Fair Park (through September 25)
Does the idea of a less-crowded Wisconsin State Fair that takes place in early fall sound appealing to you? It should, because State Fair Park’s annual Harvest Fair is always a delight. Music, food, lumberjack shows, scarecrows, pumpkin bowling, and oodles of vendors are all included in this free three-day fest.

September 24
Fromm Petfest @ Henry Maier Festival Park
Summer’s over. Woof! So why not say goodbye to the season with the always adorable Fromm Petfest? All the things you know and love will be back for this pet-tastic shindig: dock diving, lure and agility courses, the Doggie Dash speed trial, the Petfest Marketplaces, and KITTY CITY. Oh, and the whole thing is free! Don’t forget to bring your (properly leashed and vaccinated) pet!

Six Year Anniversary Party @ Third Space Brewing
Celebrate six years of Third Space Brewing with a day full of beer releases, food trucks, live music, and philanthropy. Third Space has the beer part handled. Triciclo Peru, Riley’s Pizza, and Riley’s Good Dogs will be serving up food. After WMSE’s Boogie Bang Gang DJs do their thing from noon to 3 p.m., the brewery’s newly renovated deck will feature live music from the likes of Horace Green, Sleepy Gaucho, and De La Buena. There will also be opportunities to donate to YMCA Camp Minikani, where Third Space’s founders first met!

Mobtoberfest @ Mobcraft Beer
The 5th annual Mobtoberfest will bring German-inspired beer, food, music, and games to Mobcraft’s Walker’s Point taproom and a portion of Virginia Street from noon to 11 p.m. on Saturday, September 24. Prost!

Milwaukee Comic Convention @ Wisconsin State Fair Park
Behold! More than 300 tables of comics, collectibles, characters, and more will be on hand at the Wisconsin State Fairgrounds on September 24 during the Milwaukee Comic Convention.

September 24-25
Doors Open Milwaukee @ various locations
One of Milwaukee’s most unique events is Historic Milwaukee’s annual Doors Open Milwaukee, a citywide “open house” where folks can explore the normally off-limits insides of theaters, museums, art galleries, and random businesses. This year’s edition will boast more than 100 participating sites, including new sites like Fiserv Forum, the Komatsu Customer Experience Center, and the Milwaukee Athletic Club. The complete list of sites can be found HERE.

Festa Italiana @ Italian Community Center
Festa Italiana’s big Summerfest-grounds blowout didn’t happen this year (just like it didn’t happen in 2020 and 2021), but a smaller, back-to-basics fest is set for this weekend at the Italian Community Center. Expect plenty of music, food, and fun, plus Sunday mass and a Procession to Pompeii Square.

September 25
Bean Plant Block Party @ Anodyne Walker’s Point Roastery
The inaugural Bean Plant Block Party will take place outside on Bruce Street between 2nd and 3rd, and will feature skateboard ramps and obstacles from Sky High; food from Tots On The Street; beer from Low Daily; and live music from Fake Twin, Overhand, and Piles. The event is free and open to the public. Skaters of all skill levels are welcome!

Squeak Fest @ Clock Shadow Creamery
It’s Squeak Fest! Just around the corner from Anodyne at Clock Shadow Creamery! Food! Lakefront Brewery’s Curd Wagon! Beer from Indeed Brewing Co.! Music! More!

Harbor Fest @ The Harbor District
Celebrate all things boats, fish, and water at this family-friendly festival. Harbor Fest will take place on Sunday, September 25 in front of UWM’s School of Freshwater Sciences (600 E. Greenfield Ave.). From 11 a.m. to 4 p.m., attendees can enjoy baby sturgeon releases (and a “sturgeon blessing”), a Riverkeeper Boat Parade, music performances, free boat tours, a children’s makers tent, and food from local vendors.

September 30
Bay View Gallery Night @ Bay View
Since 2011, Bay View Gallery Night has organized “Milwaukee’s largest annual celebration of art, local business, music, and community.” The massive neighborhood-wide event brings together talented area artists and musicians, along with an eclectic mix of Milwaukee bars, restaurants and retailers for a large-scale event that has quickly become a part of the Bay View tradition. It’s free. It’s fun. It’s locally-focused. What more can you ask for? How about a second Gallery Night in 2022? That’s right! A few months after hosting its spring edition on June 3, Bay View Gallery Night is back for an early autumn installment on Friday, September 30.

September 30-October 2
Milwaukee Tattoo Arts Festival @ Wisconsin Center
The 12th annual Milwaukee Tattoo Arts Festival is a celebration of all things ink, as body illustration enthusiasts and renowned tattoo artists take over the Wisconsin Center for three days of fun, connection, and tattoos.

October 2
Brady Street Pet Parade / Brady Street Art Walk @ Brady Street
What’s better than the beloved Brady Street Pet Parade? How about the beloved Brady Street Pet Parade and the previously postponed Brady Street Art Walk happening on the same day—Sunday, October 2? Yep, from 11 a.m. until 4 p.m., Brady Street will be alive, kicking, barking, and prancing with oodles of pets AND oodles of art. The parade itself will start at 1 p.m. at Brady and Franklin Place, led by Milwaukee Police Department horses and Samba da Vida drummers. The parade will make its way west to Cass Street, then south to St. Rita’s Church for the annual Blessing of the Pets by Three Holy Women’s Father Tim Kitzke. He’s a swell guy!

October 2-9
Milwaukee Comedy Festival @ various locations
Originating long before the city had anything resembling a sustainable comedy community, Milwaukee Comedy Festival has grown and evolved along with Milwaukee’s stand-up scene. In fact, the annual comedic undertaking has been an invaluable means of pushing local comedy to exciting, new territory. Along the way, Milwaukee Comedy Festival has also brought in noted national talent to headline some of its shows. This year’s festival—which will be taking place October 2-9—is no different, as Laurie Kilmartin was recently announced as the comic who would close out the 17th annual Milwaukee Comedy Festival. You can check out the full lineup HERE.

October 8
Flannel Fest @ Boone & Crockett / The Cooperage
Back in 2019, Boone & Crockett—in partnership with The Cooperage, Taco Moto, and Pedal Tavern—hosted a celebration of music, food, and seasonal attire known as “Flannel Fest.” That iteration brought hundreds of people to the Harbor District bar on a brisk fall day/night to see live music performances. We were there. It was fun! Boone & Crockett will officially be bringing Flannel Fest back in a live and in-person capacity on Saturday, October 8. This time around, Boone & Crockett’s parking lot will host a wide range of Milwaukee-based artists. You can see the eclectic and altogether impressive Flannel Fest lineup HERE.

Fall Block Party @ Enlightened Brewing Company
The last block party Enlightened Brewing Company will host this year will be an especially good one. The Bay View brewery will serve up great beers, tasty meats from Sweet Smoke BBQ, tasty treats from Creme de Liqueur and Happy Joy Candy Floss, and tunes from Driveway Thriftdwellers and Hosts.

Totally Rad Vintage Fest @ Wisconsin State Fair Park
The event description sums this up pretty nicely: “Step back to a time before Wi-Fi at Totally Rad Vintage Fest, a traveling vintage festival dedicated to the 80’s, 90’s & Y2K. Feel the nostalgia as you shop from over 80 vintage vendors, challenge a friend at the vintage arcade, show off your fit at the throwback photo ops or jam to the tunes being spun by the vinyl DJ. There is a little something for everyone inside TRVF. Vendors primarily focus on vintage clothing but you’ll also find toys, video games, home goods, memorabilia and more! Whether you’re hunting for a gem hiding in a bargain bin or searching for the collectible piece of your dreams you are sure to find it at Totally Rad Vintage Fest.”

October 14-16
Milwaukee Paracon @ various locations
Milwaukee Paranormal Conference is back! The weekend celebration of the strange and unusual is set to take place October 16-18 at various locations in and around Milwaukee. This year’s installment is described as “a celebration of the ghost stories of Milwaukee, urban legends, Milwaukee UFO sightings, Wisconsin folklore, all kinds of paranormal and all centered on phenomena that happened in the Brew City.”

Twisted Dreams Film Festival @ Avalon Theater
This fall, Twisted Dreams will assume its previous in-person form as it takes over the Avalon Atmospheric Theater on October 14-16. The seventh annual fest will feature the usual assortment of “the most twisted independent films from around the world,” as well as a bunch of other goodies. Unstoppable Troma mogul Lloyd Kaufman will be on hand for a meet-and-greet on the 14th, as will Slumber Party Massacre star Brinke Stevens. The 14th will also see the Milwaukee premiere of Uncle Lloyd’s latest Troma masterpiece, Shakespeare’s Shitstorm. On the 16th, Milwaukee horror-core band Ratbatspider will provide a live score to the classic 1922 film Nosferatu. Will the 2022 Twisted Dreams Film Festival also feature a burlesque performance? Oodles of “twisted” short films? A vaguely defined “spook show”? Of course it will.

October 14, 21, 29
Slasher Bash @ various locations
Alive And Fine owner Ashley Smith has put together a bloody good series of events this October. Slasher Bash will consist of three events in three locations over the span of three nights. Things kick off at Bad Moon Saloon on October 14 with a “Vintage Double Feature,” that’s basically a night of outdoor slasher flicks and flashlight shopping with items from 20 “killer vintage vendors.” A week later, Alive And Fine with host “The Horror Show,” which is a group gallery show featuring over 20 artists inspired by horror in cinema. Finally, the Bash will conclude at Promises on October 29, where Smith (the former singer of Whips and Red Knife Lottery) and her Ghouls Gone Wild band will play Halloween-themed tributes. There will also be a cash prize constume contest.

October 19-23
Pumpkin Pavilion @ Humboldt Park
“This four-day, family-friendly event brings over 2,000 Bay View residents and Milwaukee neighbors to Humboldt Park Pavilion. Guests come to carve pumpkins, admire the display of 1,000 lit pumpkins, enjoy live music, eat local food, and embrace the fun that is Halloween.”

October 29
Jack-O-Lantern Jubilee @ Red Arrow Park
The inaugural family-friendly Halloween event is coming to Downtown Milwaukee’s Red Arrow Park on Saturday, October 29, from 10 a.m. to 2 p.m. The first 500 attendees will have the opportunity to pick out a free pumpkin from downtown Milwaukee’s only pumpkin patch. At 12 p.m., a kids costume parade, led by popular animated movie characters, will loop around Red Arrow Park. Families can also gather for story time with Wanda the Witch, a Halloween-themed character from The Pocket Lady, at 11 a.m. and 1 p.m. And there’s more! Face painting, giveaways, food trucks, and a book sale from Friends of the Milwaukee Public Library will also be featured. The free event is intended for kids of all ages, though it’s especially suited to tykes ages 2-8.

December 4
Hover Craft @ The Pritzlaff Building
Since 2009, Hover Craft has brought skilled local artists, crafters, retailers, and others residing beneath the broad “maker” umbrella together to bring Milwaukee-made goods to area consumers during the holiday season. It’ll return to The Pritzlaff Building on Sunday, December 4.

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