1. Riverwest Jazz Fest
FRIDAY FROM 5:30 P.M.-12 A.M. | VARIOUS LOCATIONS IN RIVERWEST
The Jazz Gallery Center for the Arts has collaborated with Milwaukee Jazz Vision and the Jazz Foundation of America to organize the neighborhood’s first jazz fest. A total of seven contemporary jazz shows – including a New Orleans-style march down Center Street – will fill Friday evening at the Jazz Gallery, Bar Centro and Company Brewing.
2. Tea Leaves Pop-Up
FRIDAY FROM 6-9 P.M. | CROSSROADS COLLECTIVE
Dire Need Zine presents live music from local bands and artists Spoy, Overhand, Mizzy, Striped Cow and Falling Flat at this all-ages pop-up. Attendees are encouraged to bring clothes and food to donate, and each donor has a chance to win a $250 Crossroads Collective gift card. There’ll also be food, drink and other vendors at the dining hall.

Tell us who you’d pick to be a Betty this year!
3. Ray LaMontagne
FRIDAY AT 7:30 P.M. | MARCUS CENTER FOR THE PERFORMING ARTS
Folk singer-songwriter Ray LaMontagne plays Milwaukee this Friday with support from indie artist Tomberlin. On his Just Passing Through tour, LaMontagne will perform a fan-selected setlist of his recorded catalog.
4. Harvest Fair
FRIDAY THROUGH SUNDAY | WISCONSIN STATE FAIR PARK
Head back to the state fairgrounds this weekend to celebrate the start of fall. Harvest Fair will have 11 stages of local music, national headliners and lumberjack shows. Fairgoers also can grab autumnal treats, go pumpkin bowling or make their own scarecrow.
5. Harvest Day Festival
SATURDAY FROM 10 A.M.-3 P.M. | JOHNSON’S PARK
This annual community block party turned fall festival – organized by Walnut Way Conservation Corp. – features local music, a youth talent show, food vendors, children’s activities and community resources.
6. Best Day Ever All-Ages Story Slam
SATURDAY AT 12:30 P.M. | INTERCHANGE THEATRE
What would be your best day ever? This all-ages noncompetitive contest gives people a chance to tell personal stories related to the theme without notes or props. Attendees can choose just to listen, share their best day ever or submit an “ultra-short” story for an emcee to read.
7. Damian Lillard Welcome Rally
SATURDAY AT 2 P.M. | FISERV FORUM
It’s officially Dame Time in Milwaukee. Join the Bucks in welcoming the seven-time NBA All-Star with a celebration on the Plaza outside the stadium. Food and drink will be available to purchase, as well as a limited number of Lillard jerseys.
8. Plum Blossom Opening Reception
SATURDAY FROM 6-9 P.M. | VAR GALLERY
The emerging artist program will display works from three recent UWM and MIAD graduates as they transition to professional practice. The showcase is a result of a year-long residency for the artists to further their craft as they enter the art world.
9. Retrospekt x Evan Weselmann Camera Launch Party
SATURDAY FROM 4-10 P.M. | RETROSPEKT
The retro-inspired camera shop collaborated with Minneapolis-based artist Evan Weselmann to cover a new line of gear in his bright, bold graphics. Besides cameras, the drop includes a new collection of apparel. Gathering Place Brewing Company will provide a limited edition beer – the Break Out Pilsner – inspired by the artwork.

10. Jesse Jo Stark
SATURDAY AT 8 P.M. | THE BACK ROOM @ COLECTIVO
LA native Jesse Jo Stark fuses ’70s rock with country and ethereal pop to evoke an enchanting atmosphere. Inspired by the aesthetics of The Cramps, Elvira and late ’80s horror movies, her shows have been described as moody and otherworldly.
11. MKE Studio Tour
SATURDAY AND SUNDAY FROM 10 A.M.-5 P.M. | VARIOUS LOCATIONS THROUGHOUT MILWAUKEE
Ever wonder how local art is made? This studio tour allows people to visit the studios of Wisconsin Craft artists around Milwaukee. The tour is free and self-guided, which allows visitors to see the spaces and processes of art creation at their own pace and browse works for sale.
12. Maxwell Street Days
SUNDAY FROM 6 A.M.-2 P.M. | FIREMAN’S PARK, CEDARBURG
Four times a year, Cedarburg holds a flea market where vendors sell everything from antiques and fine art to produce and pre-loved items. The market is free to attend, with hundreds of sellers to browse.
13. Chainsaw Carving & Art Forest Festival
SUNDAY FROM 9 A.M-3 P.M. | RIVER BEND NATURE CENTER, RACINE
Watch chainsaw artists turn logs into sculptures! If a carving catches your eye, every piece created will be available for purchase during the event’s public auction. Live music, food, drink and craft vendors will be on-site, as well as family-friendly activities and live music.
14. Milwaukee Comedy Festival Kickoff
SUNDAY FROM 6:30-8 P.M. | LAKEFRONT BREWERY
The weeklong comedy extravaganza starts its 18th year with Portland’s Kelly Ryan, who won the Oregon city’s Funniest Person Contest in 2021. Sip on Lakefront Brewery’s offerings as you enjoy the joke-filled fun and the first of many performances.
