Labor Day weekend is the unofficial end of summer, since many students shortly return to school and adults are often wrapping up summer vacation plans. It's the last hurrah to enjoy summer in Milwaukee, and locals take part in all types of events to revel in the good weather and bid adieu to summer.
The city on Lake Michigan is known for breweries and the Harley Davidson Museum of motorcycles. Whether you enjoy live music, food festivals, farmer's markets, or cultural events, you'll find an easy getaway that doesn't require long travel or even lots of money, as many of these events are free.
Even if you’re not into motorcycles, you can have a blast at this outdoor Harley-Davidson five-day festival dating back to 2002. This all-American company has a long history in Milwaukee and was founded in the city in 1903. 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. Many events are centered around the local Harley Davidson Museum, located in downtown Milwaukee.
The 2020 event is scheduled for Labor Day weekend, September 3–6, and is free to attend. The event is co-organized by all of the local Harley Davidson dealerships, and the full details for the 2020 festival haven't been released as of July 29, 2020.
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, September 5–6, 2020, 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 fun at this family-friendly event, with activities like art fest bingo, spin art, and live music. Eat on-site or nearby at local restaurants or the Milwaukee Public Market.
Admission is free, but parking is limited. Most street parking is closed down and there is a $10 fee for parking at either of the Third Ward parking structures.
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 every Saturday, Sunday, Tuesday, and Thursday, from June 27 to November 1, 2020.
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!, the outdoor art gallery 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.
Wisconsin Highland Games
The Wisconsin Highland Games are canceled in 2020.
The Wisconsin Highland 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
The St. Francis Days Festival and Parade are canceled in 2020.
There’s a hodgepodge of things for people of all ages to do at the St. Francis Days Festival in Milton Vretenar Memorial Park in the town of 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
The Oak Creek Lions Festival is canceled in 2020.
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.
Cedarburg Maxwell Street Days
The Maxwell Street Days events for September 6 and October 4, 2020, are canceled.
For over 50 years, rain or shine, the Cedarburg Volunteer Fire Department has offered the popular Maxwell Street Days 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.
Laborfest in Milwaukee is canceled in 2020.
The Milwaukee Area Labor Council's Laborfest 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.