Your Guide to Weekend Fun in Milwaukee & Waukesha Counties September 25-27, 2026

Dated: September 22 2026

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Your Guide to Weekend Fun in Milwaukee & Waukesha Counties

September 25–27, 2026

Looking for something fun to do this weekend? Milwaukee and Waukesha Counties are packed with fall festivals, live entertainment, local markets, family activities, baseball and one-of-a-kind community events. Here are some great ways to enjoy the final weekend of September!

Waukesha County Events

Waukesha Oktoberfest

Friday, September 25 | 5:00–10:00 PM
Saturday, September 26 | 12:00–10:00 PM
Frame Park | 1150 Frame Park Drive, Waukesha | Free admission

Celebrate German culture with traditional food, beer, live music, dancing and plenty of Oktoberfest fun along the Fox River. Admission is free, although guests purchasing or consuming beer must buy a $2 wristband. A free shuttle will run from the Waukesha County Courthouse parking lot during select hours.

View Oktoberfest details

Waukesha Farmers’ Market

Saturday, September 26 | 8:00 AM–12:00 PM
125 W. St. Paul Avenue, Waukesha | Free admission

Start your Saturday downtown while shopping from more than 70 vendors offering Wisconsin-grown produce, meats, cheeses, baked goods, handmade items and seasonal favorites.

View market information

Piala’s 16th Annual Fall Festival

Saturday, September 26 | 9:00 AM–4:00 PM
Sunday, September 27 | 10:00 AM–3:00 PM
Piala’s Nursery & Garden Shop | S39W27833 Genesee Road, Waukesha | Free admission

Enjoy a family-friendly weekend featuring an artisan craft fair, live music, fresh food, inflatables, festival-only plant specials, resident animals, the Peacock Palace, community meet-and-greets and door prizes. Guests are also encouraged to bring a nonperishable food or household item for the local food pantry.

View festival details

Wagfest

Saturday, September 26 | 11:00 AM–5:00 PM
Mitchell Park | 19900 River Road, Brookfield

Bring your four-legged friend to this dog-friendly celebration benefiting the Elmbrook Humane Society. Wagfest brings together pets and their people for activities, vendors, food, dog games, lure courses, an adoption tent, photo opportunities and plenty of tail-wagging fun.

View Wagfest details

Indian Summer Fall Fundraiser & Native Art Market

Saturday, September 26–Sunday, September 27
Waukesha County Expo Center | 1000 Northview Road, Waukesha

Celebrate and learn about Indigenous cultures at this special fall fundraiser supporting the return of the Indian Summer Festival. The weekend is expected to feature more than 60 Native artists, Native-owned food vendors, cultural demonstrations, traditional lacrosse, dancing and teachings, plus the inaugural Miss Indigenous Wisconsin Pageant. Check the event page for the complete daily schedule and ticket information.

View event information

Milwaukee County Events

Doors Open Milwaukee

Saturday, September 26–Sunday, September 27
More than 150 locations throughout Milwaukee | Most locations are free

Go behind the scenes at historic buildings, cultural landmarks and unique spaces throughout Milwaukee. Most participating locations are free and open to the public, with additional in-depth ticketed tours available for up to $10. Hours vary by location, so make a plan before heading out.

Explore participating locations

Milwaukee Brewers vs. St. Louis Cardinals

Friday, September 25 | 6:40 PM
Saturday, September 26 | 6:10 PM
Sunday, September 27 | 2:10 PM
American Family Field | 1 Brewers Way, Milwaukee

Cheer on the Brewers during their final regular-season home series against the St. Louis Cardinals. Choose from a Friday-night game, a Saturday-evening matchup or a Sunday-afternoon game at American Family Field.

View the Brewers schedule and tickets

China Lights: Legends Come Alive

Friday, September 25–Sunday, September 27 | 5:30–10:00 PM
Boerner Botanical Gardens | 9400 Boerner Drive, Hales Corners

Walk through a glowing outdoor display featuring approximately 40 illuminated exhibits, nightly performances and cultural experiences. The route covers about three-quarters of a mile, and timed-entry tickets are required. Food and beverages are available for purchase.

View China Lights tickets and information

MAMMA MIA!

Friday, September 25 | 7:30 PM
Saturday, September 26 | 2:00 PM and 7:30 PM
Sunday, September 27 | 1:00 PM and 6:30 PM
Uihlein Hall at the Marcus Performing Arts Center | 929 N. Water Street, Milwaukee

Sing along to the timeless music of ABBA during this feel-good Broadway favorite. The story follows a mother, a daughter and three possible fathers on a sunny Greek island in a celebration of love, friendship and family.

View show details and tickets

South Shore Farmers Market

Saturday, September 26 | 8:00 AM–12:00 PM
South Shore Park | 2900 S. Shore Drive, Milwaukee | Free admission

Shop locally grown produce, meats, eggs, baked goods and other Wisconsin-made products while enjoying a beautiful view of Lake Michigan. It is an easy and relaxing way to start your Saturday in Bay View.

View Milwaukee County event information

Harbor Fest: What Lies Beneath

Sunday, September 27 | 11:00 AM–3:00 PM
Harbor View Plaza | 600 E. Greenfield Avenue, Milwaukee | Free admission

Celebrate Harbor Fest’s 10th anniversary with a free, rain-or-shine event exploring Milwaukee’s waterways. Highlights include tugboat tours, Inner Harbor boat rides, live performances, interactive exhibits, children’s activities, shipwreck stories and the opportunity to watch baby sturgeon released into the harbor.

View Harbor Fest details

Wisconsin MORE THAN PINK Walk

Sunday, September 27 | Morning event
Henry Maier Festival Park | 200 N. Harbor Drive, Milwaukee

Walk, fundraise and come together with the community to support Susan G. Komen’s mission to end breast cancer. Participants can register individually or join a team for this inspiring morning along Milwaukee’s lakefront.

Register or view event information

Make the Most of Your Weekend!

Whether you are ready for Oktoberfest fun, a farmers market, a Broadway show, Brewers baseball or a family day by the harbor, there is something for everyone happening around Milwaukee and Waukesha Counties this weekend.

Save this guide, share it with a friend and start making your weekend plans!

Looking to make a move in southeastern Wisconsin? The Hupke Team is here to help you find the perfect place to call home.

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Jennifer Hupke

Jennifer has been a trusted name in Southeastern Wisconsin real estate since 2003. With over two decades of experience, she brings a strategic, detail oriented approach to every transaction, whether i....

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