While Wisconsin gets a bad rap for its winters (and, truth be told, they are some of the coldest in the country), winter in Milwaukee has its charm. But warm weather fans are still in luck because the city has festivals, concerts, fairs and all sorts of unique distractions between spring and fall. 

Here’s a month-by-month guide for when to visit Milwaukee and what to do while you’re there.

Visitors on the Sky Ride at Wisconsin State Fair in Milwaukee
Summer in Milwaukee sees festivals galore © Matt Anderson Photography / Getty Images

High Season: June to August

Best time for festivals

Warm weather is never guaranteed in Wisconsin, but your best bet to avoid the cold is to plan your trip during the summer. Milwaukee is known for its lakefront festivals, and Summerfest, a massive multi-week music festival, draws the biggest crowds of out-of-town visitors.

Even during high season, Milwaukee is fairly affordable, but expect to pay higher prices during the warm summer months, particularly for accommodations. Downtown Milwaukee and nearby neighborhoods will be the priciest, but that’s also where you’ll find the most activities.

Bicyclists and walkers on the Oak Leaf Trail in Milwaukee, Wisconsin
Bicyclists and walkers on Milwaukee's Oak Leaf Trail, which is more than 100 miles long © Joe Ferrer / Shutterstock

Shoulder Season: March to May and September to November

Best time for outdoor activities

Cool – but not too cool – weather makes fall and spring the perfect time to explore the city. Milwaukee’s Oak Leaf Trail network offers more than 100 miles of walking and biking trails through urban, suburban and rural areas, and it passes alongside top attractions like the Milwaukee Art Museum and waterfront parks and restaurants.

Though November and March can sometimes be fairly cold, spring and fall months are generally quite pleasant. As nearly half of the state is covered with trees, Wisconsin is also an ideal destination to catch fall foliage, which usually peaks in late September or early October.

Low Season: December to February

Best time for indoor and artsy events

Winter might be Milwaukee’s slow season, but you’ll still find plenty to do in town. From holiday markets and ice skating to quirky festivals and winter surfing (yes, really!), you’ll enjoy smaller crowds and lower prices without having to sacrifice any fun.

Swimmers in the water at the Milwaukee Polar Bear Plunge
Walking into the chilly Lake Michigan waters for the Polar Bear Plunge on New Year’s Day © Aaron of L.A. Photography / Shutterstock


January is the quietest (and coldest) month of the year in Milwaukee, but for those who can handle the chill, the Polar Bear Plunge is an unforgettable way to ring in the new year – by swimming in icy Lake Michigan with a bunch of strangers!
Key events: Cool Fool Kite Festival, Polar Bear Plunge


It’s still freezing outside in February, so Milwaukee keeps the fun indoors. Beer is still the city’s official drink, but with these temperatures, you’re more likely to find hot cider and chocolate.
Key events: Anime Milwaukee, Burnhearts Mitten Fest


Higher temperatures mean the snow is beginning to melt just in time for baseball season. In the event that it snows (and it often does in March), the Brewers have a retractable roof on their stadium to keep fans warm and dry.
Key events: St. Patrick’s Day Parade, Brewers’ Opening Day


The entire city is in full bloom, and countless gardens and parks are overflowing with tulips, daffodils and lilacs. Seasonal attractions and walking tours begin opening mid-month.
Key events: Art in Bloom, Milwaukee Film Festival


You can begin to feel fairly confident that no snow will fall in Milwaukee this month, but even if it does, most events are still indoors. For those who prefer outdoor activities, cycling season is getting started.
Key events: Memorial Day

Participants walking in the streets for the Juneteenth parade in Milwaukee, Wisconsin
A drum band in Milwaukee’s 2021 Juneteenth parade © Aaron of L.A. Photography / Shutterstock


Milwaukee’s festival season officially begins in June, with everything from small neighborhood events to community-wide Pride Month celebrations.
Key events: Pride Fest, Juneteenth, Water Lantern Festival


Often the hottest and most humid month of the year, July is the time to kick back and relax at one of Milwaukee’s many beaches. Bradford Beach is near downtown attractions like the Milwaukee Art Museum, and it’s the perfect place to swim, picnic, bike or join a game of beach volleyball.
Key events: Riverwest 24 Bike Race, Croatian Fest, Armenian Fest, Milwaukee Brewfest, Festa Italiana

The 10 best beaches in Wisconsin


There isn’t a weekend without a festival in August, so although the crowds will be thicker, visitors are pretty much guaranteed a good time.
Key events: Wisconsin State Fair, Mexican Fiesta, Milwaukee Fringe Festival, Irish Fest, Waukesha BluesFest, IndiaFest, Bloody Mary Festival

Milwaukee Summerfest entrance
Summerfest is one of Milwaukee's big events © Tony Savino / Shutterstock


Summer may be over, but the weather is still warm and festivals remain in full swing. Milwaukee's main draw in September is the lakefront festival Summerfest, considered to be the world’s largest outdoor music festival. Summerfest is currently taking place in September, but it has previously been held in July, and the organizers said they may switch it back to summer months at some point in the future. Over at the State Fairgrounds, Harvest Fair is gearing up for corn mazes, pumpkin carving and hay rides.
Key events: Summerfest, Third Ward Art Festival, Harvest Fair, Milwaukee Rally


Chilly days and even chillier evenings are perfect for exploring Milwaukee by foot or bike. Though the city has slowed down a bit, you’ll still find at least one festival going on every weekend.
Key events: Milwaukee Lakefront Marathon, PrideToberFest, Milwaukee Comedy Festival, Oktoberfest


Christmas is big in Milwaukee, and holiday markets and light displays usually get started in late November, including Country Christmas, the state’s largest drive-through holiday light display.
Key events: Holiday Folk Fair International, Country Christmas


Aside from the holiday markets, December is a slow – and very cold – month in Milwaukee. The city is shut down on Christmas Day.
Key event: Christkindlmarket

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Midwest travel ideas: 8 under-the-radar destinations to visit in America’s Heartland
300 miles of beer, brats and cheese: a Wisconsin culinary tour
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