Your Guide to Weekend Fun in Milwaukee & Waukesha Counties: September 11-13, 2026

Late-summer weekends in Wisconsin are hard to beat! From festivals and live music to food, family activities and cultural celebrations, there is plenty happening throughout Milwaukee and Waukesha Counties.

Here are some of The Hupke Team’s top picks for the weekend!

Milwaukee County Events

TosaFest 2026 - Wauwatosa

When: Friday, September 11, 5-11 PM and Saturday, September 12, 11 AM-11 PM
Where: The Village of Wauwatosa

TosaFest is celebrating its 50th anniversary! Enjoy live music on three stages, five beer gardens, KidsFest, local food, a vendor market, Oktoberfest activities and more.

View TosaFest details!

Puerto Rican Festival of Wisconsin - Milwaukee

When: Saturday, September 12
Where: Henry Maier Festival Park

Experience a full day celebrating Puerto Rican culture with live music, dancing, authentic food, cooking demonstrations, artisan vendors and family-friendly activities. Tickets are available online.

View festival details and purchase tickets!

FREE Sunday Family Fun Day - Milwaukee

When: Sunday, September 13, 10 AM-2 PM
Where: Northwestern Mutual Community Park at Henry Maier Festival Park

This free family event celebrates the performing arts with music, dance, creative activities and performances from local arts organizations. Families can also enjoy the park’s inclusive playground and purchase food from local vendors.

View Family Fun Day details!

Waukesha County Events

Oconomowoc Fall Fest - Oconomowoc

When: Friday, September 11, 4-9 PM and Saturday, September 12, 9 AM-9 PM
Where: Downtown Oconomowoc and the Village Green

Kick off fall with live music, food trucks, a beer garden, local vendors and children’s activities. Saturday also features a complimentary trolley running throughout the day.

View Oconomowoc Fall Fest details!

St. Charles Fall Fest - Hartland

When: Friday, September 11 through Sunday, September 13
Where: St. Charles Parish, 313 Circle Drive, Hartland

This three-day festival includes carnival rides, live music, food, raffles, a bags tournament and plenty of family fun. The carnival runs from noon-11 PM on Friday and Saturday and noon-5 PM on Sunday.

View the complete Fall Fest schedule!

Neighborhood Beer Garden - Waukesha

When: Friday, September 11, 5-9 PM and Saturday, September 12, 3-9 PM
Where: Merrill Crest Park, 616 S. University Drive, Waukesha

Gather with friends and neighbors for live music, local food trucks and Oktoberfest-style beer. Friday features music from Tonight Only, while Dean Richard and Stray Voltage perform on Saturday. This event is weather permitting.

View Neighborhood Beer Garden details!

Make the Most of Your Weekend!

Whether you’re looking for live music, delicious food or something fun for the entire family, Milwaukee and Waukesha Counties have plenty to explore this weekend. If you are looking to buy or sell, The Hupke Team is here to help!

Event details may change, so check the official event pages before heading out. 

Enjoy your weekend!