Though it’s an affordable year-round destination, Madison still has a popular high season from June through October, when average highs range from the low 80s to the high 60s, and warm summer skies are followed by golden fall foliage. In the summer, shop the largest producer-only farmers market in the country at the Dane County Farmers’ Market on the Square. In July, Art Fair on the Square brings 500-juried artists and a festive event organized by the Madison Museum of Contemporary Art. Top athletes from around the country and 45,000-plus spectators descend in September for the U.S. Ironman Wisconsin. Cooler fall breezes come in October, when University of Wisconsin-Madison’s homecoming celebrations paint the town.
For lighter crowds and still-pleasant weather, visit Madison during its shoulder-season months of November, April, and May. A notoriously fickle spring month, April often means a mix of rain and cool weather with peaks in the 60s. May is also rainy, but temperatures climb into the 70s and there’s this: the world’s largest Brat Fest, a Memorial Weekend celebration of epic Wisconsin proportion. For another serious midwestern festival, come in November for the annual Wisconsin Original Cheese Festival, with everything from artisan cheeses and dinners to creamery tours and tastings.
Madison’s low season and the heart of its cold and snowy winter run from December through March, with average highs teetering between 20 and 30 degrees and lows around 15 degrees. This is the time to find the very best deals to Madison, especially if you enjoy winter sports like snow sailing, ice fishing, and even cycling—thanks to Madison’s well-maintained bike trails. January may be the coldest month, but that’s when tough-as-nails cyclists come out to play.