Most schools are back in session the week of Labor Day, and so the three-day stretch over the holiday weekend is the last hurrah of summer. Thankfully there are plenty of ways to enjoy the holiday that also celebrate the hardworking culture of the United States in the Milwaukee, Wisconsin area.
Even if you’re not into motorcycles, you can have a blast at this outdoor Harley-Davidson five-day festival dating back to 2002. The festivities include custom bike and stunt shows, new demo models, food and drink for purchase, live music, and rides on Harleys. Pick your location—Milwaukee, Oconomowoc, Thiensville, West Bend, or New Berlin—or toggle between a few. The event also offers the Milwaukee Rally Women's Ride and the Run for Cash, plus a museum in Milwaukee.
Wisconsin Highland Games
The Games, held at Waukesha Expo Center, include family-friendly activities celebrating all the cultures of the British Isles and the Celtic nations, including Britain, Wales, Ireland, and others. Activities include things like highland dancing, ax and knife throw, longbow, piping and drumming, and single-stick fencing. Celtic dogs are available for petting, too, such as Irish wolfhounds, Scottish deerhounds, and golden retrievers.
The festival runs from Friday afternoon until Sunday night of Labor Day weekend, with live music and drinks extending later into the evening; however, food vendors and many of the exhibits begin closing in the afternoon.
During the opening ceremonies on Friday, admission and parking are free. There is no charge for kids 12 and under.
St. Francis Days
There’s a hodgepodge of things for people of all ages to do at this Labor Day weekend event in Milton Vretenar Memorial Park in St. Francis, about 10 minutes south of Milwaukee by car.
At this four-day gathering which has taken place for over 50 years, you'll find everything from a martial arts demonstration to a polka mass to a petting zoo, in addition to nightly live music and the city’s largest parade, which kicks off on Saturday late morning. Food options include a fish fry, a rib dinner, and other options.
Admission and parking are free.
Oak Creek Lions Festival
This festival, hosted annually by the Oak Creek Lions Club, is about a 20-minute drive south of Milwaukee and offers live music at one indoor and one outdoor stage. On Friday, they honor the elderly with a senior day featuring a fish fry, entertainment, and raffles. Saturday is full of free kids' activities like face painting, balloon art, and live music.
The Polka Mass and Car Show take place on Sunday. On Monday, veterans with military identification are honored with a free meal—thanks to the Lions Club. Carnival ride tickets are for sale for the whole weekend. Be sure to come hungry as the food choices include turkey legs, corn on the cob, chicken tenders, and more. Non-alcoholic and alcoholic drinks are served.
Big Gig BBQ
If you’re a barbecue fan, you need to be at Henry Maier Festival Park (where Summerfest is held) in Milwaukee on the Sunday of Labor Day weekend when several of the region's best BBQ restaurants serve food in one place, both in tasting size and regular portions. Along with the meats are live music shows by various bands. The Big Gig BBQ also includes fun and games like the $5K Giveaway and an Amateur Rib Cooking Competition.
The event typically has free admission and parking (for motorcycles too).
Cedarburg Maxwell Street Days
For over 50 years, rain or shine, the Cedarburg Volunteer Fire Department has offered this popular flea market at Firemen's Park near downtown Cedarburg's historic district; it's the major fundraiser for the department. Held four times each year, one of them is the Sunday of Labor Day weekend. About 600 vendors sell a mix of antiques, crafts, seasonal items, produce, art, and more.
More than 100 volunteers along with their family and friends serve food and drinks and help with the event in general. Arrive early morning so you have time to pore over all the items before the flea market closes in the early afternoon.
There is no cost for admission.
The Milwaukee Area Labor Council's event starts in the late morning with a parade led by the state's Harley Davidson motorcycles, followed by annual Classic Cars, kicking off at Zeidler Union Square Park. The parade ends at the Henry Maier Festival Park, also known as the Summerfest grounds, and that's when Laborfest starts. Enjoy the union industry display of union-made products and services, raffles with cash prizes, a classic car show, wrestling, live music, food and drinks for purchase, and additional activities.
All of the family-friendly entertainment is free.
Third Ward Art Festival
In Milwaukee's historic Third Ward, you'll find creative inspiration like art studios in former warehouses, galleries, and performing arts venues. It's a fine time to get artsy on the Saturday and Sunday of Labor Day weekend at the Third Ward Art Festival, featuring almost 150 juried artists displaying and selling their painting, jewelry, sculptures, pottery, photography, and more.
All ages are welcome to enjoy the colorful fun like art fest bingo and spin art, and live music. Eat on-site or nearby at local restaurants or the Milwaukee Public Market.
Admission is free. Park on the street or at one of the many garages close by.
The Fondy Farmers Market
If you are looking for some fresh fruits and vegetables or would enjoy an educational cooking demo, the Fondy Farmers Market has been around 100 years and is one of the most diverse and large farmer's markets in the state. It's recognized around the country for connecting low-income people with the positive features of farmers' markets.
Adults and children shop in the open air, checking out the more than 40 farmers and local food producers at the daytime market, open four days a week until the end of October.
Stroll on the Milwaukee Riverwalk
If you feel like being outside and taking in some nice views by foot on a summer evening, travelers and locals alike have enjoyed the Milwaukee Riverwalk since the 1990s. The path goes north to south, spanning more than 20 blocks and connecting three neighborhoods along the river: the Historic Third Ward, Downtown, and Beerline B. It's enjoyable to view the public art displays like RiverSculpture!, with permanent and temporary installations.
You'll also have a chance to see Riverwalk Park, water taxi landings, shops, restaurants, cafés, and brewpubs. The downtown area passes by the city's biggest theater district, which includes the Milwaukee Repertory Theater, Milwaukee Symphony Orchestra, and several other highlights.