Labor Day Weekend is the unofficial farewell to summer, and it’s the perfect excuse to get out, explore, and enjoy everything Southeast Wisconsin has to offer.
Whether you’re planning a family getaway, a couple’s weekend, or simply looking for one more summer adventure, Waukesha and Milwaukee Counties are packed with things to see and do. From live music and baseball games to local traditions and outdoor fun, there’s something for everyone.

Start Your Weekend with Live Music in Milwaukee

Brad Paisley at the BMO Pavilion 
Friday, September 4
Kick off Labor Day Weekend with a night of live music at Milwaukee’s scenic lakefront concert venue. Located in the Historic Third Ward, the BMO Pavilion combines a vibrant concert atmosphere with beautiful waterfront views and easy access to some of the city’s best restaurants and nightlife. Special guests include Jake Worthington and Laci Kaye Booth.

Experience a Unique Cultural Tradition

Wisconsin Highland Games at Waukesha County Expo
September 4-6, 2026
If you’re looking to experience something a little different this Labor Day Weekend, the Wisconsin Highland Games at the Waukesha Expo offer a memorable blend of sport, culture, and tradition. This long-standing event brings Scottish heritage to life through high-energy competitions like caber tossing and hammer throwing, along with the unmistakable sound of bagpipes filling the air. Guests can explore cultural demonstrations, browse artisan vendors, and enjoy traditional foods that highlight the richness of Scottish tradition. It’s a lively, engaging way to try something new while connecting with a unique and time-honored celebration right here in Waukesha County.

Be Part of a Legendary Baseball Rivalry
Chicago Cubs vs. Milwaukee Brewers at American Family Field

Monday, September 7 at 1:10 PM
Heading to a Brewers game at American Family Field is a classic experience, whether you’re a lifelong fan or just along for the atmosphere. The retractable-roof stadium ensures a comfortable day no matter the weather. Game-day energy, complete with tailgating, local food favorites, and crowd traditions, makes it easy to get caught up in the excitement. It is an ideal outing for families, groups, or anyone wanting to experience a true Milwaukee staple.

Enjoy a DockHounds Game in Lake Country
Lake Country DockHounds at Wisconsin Brewing Company Park
Home Games September 4-7, 2026
For a more laid-back take on baseball, the Lake Country DockHounds in Oconomowoc provide a charming alternative. The setting at Wisconsin Brewing Company Park feels intimate and easygoing, with scenic surroundings and a family-friendly vibe. You can enjoy the game without the crowds of a major league stadium, grab a local craft beer, and settle in for a relaxed evening. It’s a great way to enjoy the sport while staying closer to the quieter side of Lake Country.

Soak Up the Last Days of Summer Around the Water
Pewaukee Lake Water Ski Club
Monday, September 7, 2026  from 5:30pm-7:00pm
Labor Day Weekend is also the perfect excuse to spend as much time outdoors as possible. The Pewaukee Lake Water Ski Club’s Labor Day show is a standout highlight. Watching skiers perform intricate formations, barefoot runs, and high-flying stunts against the backdrop of the lake is both nostalgic and impressive. Nearby parks and lakefront spaces offer plenty of room to picnic, walk, or simply take in the views.

Wild Fun for All Ages
Milwaukee County Zoo
Now through Sept. 7, 2026 - 9:30 a.m. to 5 p.m.
For families looking to spend some time outside, the Milwaukee County Zoo provides a full day of exploration, with wide walking paths, interactive exhibits, and plenty of opportunities for kids to stay engaged. Labor Day marks the final day of the zoo's summer season, meaning it is your last chance to enjoy seasonal features like Animals in Action, Goat Yard and the Kohl's Wild Theater performances.

Rain or Shine, the Fun Never Stops

Springs Water Park at The Ingleside Hotel
If you’re traveling with kids or just want to keep that carefree summer feeling going, Springs Water Park is an easy addition to your weekend plans. With a mix of water slides, a relaxing lazy river, activity pools, and areas designed for younger guests, it offers something for every energy level. It’s especially convenient when you need a weatherproof option that still feels like summer.

Make The Ingleside Hotel Your Labor Day Home Base
The best part about spending Labor Day Weekend in Waukesha and Milwaukee Counties is how much you can experience in just a short drive. From concerts and sporting events to festivals and family adventures, you can fill your weekend without spending hours in the car.

When you stay at The Ingleside Hotel, you’ll enjoy:
     ●     Convenient access to Milwaukee and Lake Country attractions
     ●     Comfortable accommodations for couples, families, and groups
     ●     On-site dining at Didi’s Supper Club
     ●     Springs Water Park access for overnight guests
     ●     Experience Ingleside Program

Plan Your Labor Day Getaway
Summer goes quickly! Make the most of one of the last big weekends of the season. Book your Labor Day Weekend stay at The Ingleside Hotel and enjoy the best of Lake Country and Milwaukee from one convenient location.