Things to Do in Waukesha County & Milwaukee County This Weekend ☀️

Wisconsin summer weekends do not mess around. The second we get a stretch of warm weather, everyone collectively decides we need live music, food trucks, farmers markets, festivals, art, lakefront views, and at least one reason to say, “We should probably get there early for parking.” If you are looking for things to do in Waukesha County and Milwaukee County the weekend of May 29 to 31, there are plenty of fun options, from family festivals and farmers markets to art nights, BBQ, live music, and one very Milwaukee excuse to spend your Sunday on Locust Street. 🎶🌭

Milwaukee County

Bay View Gallery Night 🎨

🗓️ Date: Friday, May 29

🕘 Time: 5:00 PM - 10:00 PM (times vary by location)

📍 Location: Bay View neighborhood, Milwaukee (varries)

💲 Cost: FREE, but you decide the rest!

Bay View Gallery Night is a great Friday night pick if you want something that feels local, creative, and easy to wander. The event takes place throughout the Bay View neighborhood with art, music, small businesses, and family-friendly stops across multiple locations. It is one of those nights where you can say you are “just going to check out one thing,” then somehow end up walking Kinnickinnic Avenue for three hours with coffee, snacks, and a new appreciation for Milwaukee’s art scene. Most listed events are free and open to the public, which makes this a low-pressure way to kick off the weekend.

Milwaukee Tattoo Festival 🖤

🗓️ Dates: Friday May 29, Saturday May 30, & Sunday May 31

🕘 Time: 1:00 PM - 10:00 PM, 11:00 AM - 10:00 PM, 11:00 AM - 7:00 PM

📍 Location: 400 W. Wisconsin Avenue, Milwaukee

💲 Cost: Tickets are on sale right now! 

• Single Day ticket → $27.50

• 3 Day Weekend Pass → $60.00

The Milwaukee Tattoo Festival is back at the Baird Center for a full weekend of tattooing, art, shopping, contests, live art competitions, and people who are much cooler than the rest of us pretending we are not intimidated by their sleeve tattoos. The festival lists more than 200 tattoo artists, 30+ vendors, and multiple awards, so this is a solid option whether you are booking new ink, browsing artists, or just love creative events with a serious personality.

Smoke On The Water, MKE’s BBQ & Brews Fest 🍖

🗓️ Date: Saturday, May 30

🕘 Time: 11:00 AM - 4:00 PM

📍 Location: Henry Maier Festival Park → 200 N. Harbor Drive, Milwaukee

💲 Cost: 

• VIP → $75

• General Admission → $12

• Children 10 & Under → FREE Admission

• + BBQ

Smoke On The Water brings BBQ, brews, and live music to the lakefront, which is pretty much Milwaukee’s love language. The event features BBQ vendors serving tasting-sized portions starting at $5, plus full-size favorites for anyone who is not here to “just sample.” General admission is listed at $6 in advance and $12 the week of the event, with VIP options also available. This is a great pick if you want festival season energy without committing to an all-day marathon.

West Allis Farmers Market 🌽

🗓️ Date: Thursday, May 28 & Saturday, May 30

🕘 Time: 12:00 PM - 5:00 PM & 1:00 PM - 5:00 PM

📍 Location: 6501 W. National Ave, West Allis

💲 Cost: FREE to rome, you decide the rest!

Not a morning person? Perfect. The West Allis Farmers Market gives you a Saturday afternoon market option, running from 1:00 PM to 5:00 PM. The market’s 2026 season includes seasonal produce, fresh meats and eggs, specialty foods, food trucks, local brews, baked goods, coffee, and more. This is a good option if your Saturday starts slowly, because not everyone is built for an 8:00 AM farmers market and that is okay. 

Food Truck Friday + Mini Market 🍔

🗓️ Date: Friday May 29

🕘 Time: 5:00 PM - 8:00 PM

📍 Location: 6501 W. National Ave, West Allis

💲 Cost: Free entry, your stomach might take control!

Food Truck Friday + Mini Market is a great Friday night option if your idea of dinner is “everyone pick something different and we will meet back at the table.” Held at the West Allis Farmers Market, this outdoor summer event features 18+ rotating food trucks with everything from BBQ and tacos to pizza, empanadas, donuts, tater tots, desserts, drinks, and plenty in between. The May 29 event also includes live music from Tenley Sheldon, craft beer from Perspective Brewing and OPE! Brewing Co., plus a mini art and craft market with Oniomania. Admission is free, which means your only real challenge is deciding whether dessert counts as a second dinner. Spoiler, at a food truck event, it absolutely does.

Bike Rodeo 🚴‍♀️

🗓️ Date: Sunday May 31

🕘 Time: 11:00 AM - 1:00 PM (Participants must check in my noon)

📍 Location: 6501 W. National Ave, West Allis

💲 Cost: FREE, registration required!

The West Allis Bike Rodeo is a great Sunday activity for families with kids ages 4-14. Hosted by the Southwest Suburban Health Department and the Liberty Heights Park Neighborhood Association, this free event helps kids build bike safety skills in a fun, hands-on way. Participants can bring their bikes and enjoy safety checks, free helmets while supplies last, helmet fitting and decorating, seven skill courses, lunch, and raffle prizes. Basically, it is a win for kids who want to ride around and a win for parents who would prefer fewer “watch this!” moments that end in grass stains. 

Locust Street Festival of Music and Art  🎶

🗓️ Date: Sunday, May 31

🕘 Time: Stats off at 11:30 AM

📍 Location: 801 E. Locust Street, Milwaukee

💲 Cost: FREE to attend, but enjoy what you please!

Locust Street Festival is back on Sunday, May 31, and it is one of Milwaukee’s most personality-packed street festivals. The 2026 event includes four live music stages, local vendors, artists, food, beer, and the Locust Street Beer Run sponsored by Black Husky Brewing. This festival started back in the 1970s after Riverwest neighbors opposed widening Locust Street, then celebrated when the plan changed. Very Milwaukee. Very neighborhood. Very “we saved the street, now let’s throw a party.”

Waukesha County Events

Okauchee Lions Days 🎡

🗓️ Date: Friday May 29, Saturday, May 30, & Sunday, May 31

🕘 Time: 4:00 PM - 11:30 PM, 8:00 AM - 11:30 PM, & 8:00 AM - 4:00 PM

📍 Location: Okauchee Lions Park & Pavilion→ N49W34400 E. Wisconsin Avenue, Okauchee

💲 Cost: FREE admission!

Okauchee Lions Days is one of the big Waukesha County weekend events to have on your radar. This community festival runs all weekend and includes carnival games and rides, a food court, youth baseball, and live music. Admission is free, which is always nice because we all know carnival snacks have a way of becoming their own line item in the family budget.

Waukesha Farmers’ Market 🍓

🗓️ Date: Saturday, May 30

🕘 Time: 8:00 AM - 12:00 PM

📍 Location: 125 W. St Paul Avenue, Waukesha

💲 Cost: FREE entry, but your basket decides the rest!

The Waukesha Farmers’ Market is a classic Saturday morning choice and a great way to support local farmers, makers, and small businesses. Located in Downtown Waukesha, the market features more than 70 vendors with Wisconsin-grown, raised, and handmade products, including produce, meats, cheeses, baked goods, arts, and crafts. It is also a good excuse to grab coffee, stroll downtown, and convince yourself that buying fresh flowers counts as being productive. Honestly, it does.

Oconomowoc Summer Farmers’ Market 🧺

🗓️ Date: Saturday, May 30

🕘 Time: 8:00 AM - 12:00 PM

📍 Location: Bank Five Nine Campus Lot, 155 W. Wisconsin Avenue, Oconomowoc

💲 Cost: FREE entry, but your tastebuds decide next!

If you are closer to Lake Country, the Oconomowoc Summer Farmers’ Market is another strong Saturday morning option. This long-running market has been part of the community for more than 40 years and includes produce, herbs, baked goods, plants, honey, cheese, jams, maple syrup, breads, eggs, meats, and handmade items. Add a walk near downtown Oconomowoc afterward and you basically have the perfect “I did something cute this weekend” morning.

Make the Most of the Weekend 🏡

Whether you are heading to a farmers market in Waukesha, checking out art in Bay View, grabbing BBQ on the lakefront, or spending Sunday in Riverwest, this weekend is a good reminder of why people love living in Southeastern Wisconsin. The neighborhoods have character, the communities show up, and there is always something happening within a short drive.

At The Hupke Team, we are proud to call these communities home and even prouder to help people find their place in them. With 102 units sold in 2025, over $34 million in sales, and over 250 five-star reviews, we know local living is about more than the house. It is about the weekends, the neighborhoods, the favorite markets, the summer festivals, and finding a community that feels like home.

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