Michael Holloway
Entertainment

Harvest Fun for Everyone

Flannel Fest, Comedy Fest and The Low Down.

By - Oct 9th, 2025 07:59 pm
Milwaukee Public Market Harvest Festival. Photo courtesy of Milwaukee Public Market.

Milwaukee Public Market Harvest Festival. Photo courtesy of Milwaukee Public Market.

It’s officially starting to feel like fall, and this weekend’s events certainly reflect the seasonal transition. The plaza outside the Baird Center will feature a giant interactive pumpkin as part of its Halloween Village, an experience that will provide photo opportunities with ghosts and ghouls as well as free family-friendly activities. The Cooperage’s annual outdoor music festival Flannel Fest will see an iconic Milwaukee band perform its farewell show and the Milwaukee Comedy Festival will bring big-name acts to numerous venues throughout the city.

October 9-12: Milwaukee Comedy Festival

Funny folks from all over the country will gather in Milwaukee this weekend for the Milwaukee Comedy Festival, a four-day event that will span multiple venues. The festival will kick off with a performance by Patton Oswalt at Pabst Theater on Friday followed by shows at Shank Hall and ComedySportz. Those shows will feature other big-name comedy acts such as Aparna Nancherla, Sean Patton and Punkie Johnson. For more information on specific showtimes and ticket prices, visit the Milwaukee Comedy Festival website.

October 11: Harvest Festival

The Milwaukee Public Market is celebrating its 20th anniversary with Harvest Festival, a celebration featuring free family-friendly activities and entertainment. Guests can enjoy seasonal beverages like the Lakefront Brewery Pumpkin Ale while shopping at the various vendors at the Mini Harvest Market. Enjoy a variety of free activities like creating your own scarecrow and painting pumpkins, and enjoy live music courtesy of Pay the Devil and Bluegrass Allstars. The Harvest Festival will run from 11 a.m. to 4 p.m. at the Riverwalk Commons across the street from the Milwaukee Public Market.

October 10-31: Halloween Village at Baird Community Commons

The Baird Community Commons will transform into an autumn-inspired interactive experience called Halloween Village. Guests will have the opportunity to pose with a variety of interactive figures such as ghosts and witches and can walk through a giant, 12-foot pumpkin. The main event on Oct. 25 will feature family-friendly activities such as face painting, live entertainment, a children’s book sale and more. There will also be fall-themed vendors on site slinging food and beverages. Halloween costumes are encouraged, and guests will also leave with a free pumpkin while supplies last. The event is free and open to the public. More information is available on the event website.

October 11: Flannel Fest

The Cooperage is once again hosting the annual Flannel Fest, an outdoor fall-themed music festival. Dozens of local food trucks will set up shop while bands like Platinum Boys (playing their final show) and Caley Conway will perform. Guests can also browse a variety of vendors, and enjoy a stunt show courtesy of the Division BMX Stunt team. Boone & Crockett will be open indoors serving its full selection of beverages as well as outdoors selling craft beer and specialty hot and draft cocktails. Flannel Fest is free to attend and will run from 2 p.m. to 11 p.m.

October 12: Riverwest Fall Market

Records, vintage clothing, collectibles and more will be on sale at Riverwest Garden Park as part of the Riverwest Fall Market. Vendors such as Atomic Records, Rush Mor Records, Almost Home Cat Rescue MKE and more will set up booths, and shoppers can grab beverages and food from nearby businesses such as Black Husky Brewing and Scardina Specialties. The Riverwest Fall Market is free to attend and will run from 12 p.m. to 5 p.m.

October 11: The Low Down

Indeed Brewing’s Oktoberfest celebrations are winding down, but not without one last party. The Low Down will shut down the block of 2nd Street between Bruce and Virginia streets for some live music, food offerings, unique vendors and plenty of beer. The event will kick off with WMSE DJ Ascot followed by performances from bands like Cozy Danger and more. There will also be a stein-holding contest, a tie dye station, Beer Brûlée and more. The Low Down is free to attend and will run from 12 p.m. to 10 p.m.

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