7 Quirky Madison Events to Add to Your Calendar This Year

From Madison’s history as a counterculture hub in Wisconsin to its obsession with its flamingo mascot, this vibrant college town embraces the unconventional while celebrating its strong sense of community.

Want to help keep Madison weird? Don’t miss these unique events!

Frozen Assets 5k

🗓️ When and where it’s happening: Saturday, February 7, 2026 (typically the first Saturday in February) at the Edgewater Hotel.

❄︎ What it is: The Frozen Assets 5k is part of a winter festival organized by Clean Lakes Alliance that helps the community connect with and care for Madison’s fantastic lakes. Come for the thrill of running, walking, snowshoeing, or skiing across Lake Mendota and back and stay for the other attractions: ice skating, hot chocolate, kites, skydiving jumps (!!!), and more. Learn all about the festival—and sign up for the 5k—here.

⭐ Why you should go: This is one of the only 5ks worldwide to be held entirely on a frozen body of water! The scene at the start line is unlike any other: participants hoot and holler, bounce up and down to “Jump Around” to stay warm, and take in a sweeping view of kites and the state capitol building before shuffling off across a frigid Mendota. And it’s a worthy fundraiser for educational programming, lake improvement projects, water quality monitoring, and other initiatives.

Brat Fest

🗓️ When and where it’s happening: May 23-25, 2026 (Memorial Day Weekend) at the Alliant Energy Center

🌭 What it is: This food and music festival is quintessentially Madison. It’s been happening since 1983, is volunteer-run, supports local nonprofits, and best of all it’s free entry. A friend who lived in Madison as a kid and has since moved away waxed poetic about Brat Fest and we knew we had to check it out. We were not disappointed. Traditional and vegan brats are served with the option of adding sauerkraut, onion, relish, and mustard as bands play rock, hip hop, pop, funk, country, and other genres. See this year’s lineup here.

⭐ Why you should go: In short, Brat Fest is an experience! Stop by to kick off the summer, enjoy a beer and a brat (or two or three), visit the petting zoo, ride the ferris wheel, and have the whole carnival experience.

Fools Flotilla

🗓️ When and where it’s happening: June 2026 (stay tuned for the exact date!) from Tenney Park Boat Launch to Yahara River Place

🛶 What it is: If you like canoeing, kayaking, parades, costumes, and general frivolity, this is the event for you! Rain or shine, boaters in non-motorized watercraft descend on Tenney Park dressed as pirates, bananas, vikings, and dinosaurs, donning wigs, goofy hats, and other whimsical articles of clothing. Some decorate their boats; others make their own boats! (One year we saw a man paddling in a plastic Fisher-Price boat toy turned actual boat.) Participants join the event, powered by River Alliance of Wisconsin, for free but register ahead of time.

⭐ Why you should go: It’s a party on the river! There’s a wonderful sense of camaraderie, and spectators line the riverbanks and overpasses to wave and cheer. It all ends at the Marquette Neighborhood Association’s Waterfront Festival, where you can enjoy music, food, and drinks at Yahara Park.

Boaters gather at the end of the floating parade.

Midwest Log Rolling Championships

🗓️ When and where it’s happening: June 2026 (stay tuned for the exact date!), Wingra Park

🪵 What it is: This event has been on our radar but we have yet to check it out! Competitors take part in the classic lumberjack sport of log rolling and range from young kids to older adults and from amateurs to elites. Entry fees go to support the Huntington’s Disease Society of America.

⭐ Why you should go: Log rolling seems difficult, fun to watch, and one-of-a-kind. Maybe we’ll see you at this year’s event?!

Yahara Witches Paddle

🗓️ When and where it’s happening: October 2026 (date to be announced on Facebook), Tenney Park Boat Launch

🧙🏼 What it is: It’s another fantastic flotilla on the Yahara River, this time for Halloween! The Yahara Witches Paddle began six years ago as a small gathering between friends and has grown into a popular event in which people dress like witches and warlocks and paddle to the center of Monona Bay to form a Magic Circle.

⭐ Why you should go: There’s a strong sense of community out on the river, with paddlers chatting with one another as they drift down the river, cackling intermittently.

Santa Cycle Rampage

🗓️ When and where it’s happening: December 12, 2026 (date tentative), starts at Breese Stevens Field

🚲 What it is: The Madison Santa Cycle Rampage is a bike ride during which cyclists dress up like Santa, Mrs. Claus, The Grinch, a reindeer, or another festive character. We’ve been to the much larger Santa Cycle Rampage in Milwaukee but haven’t experienced its Madison counterpart yet. The rides involves plenty of food, drinks, and a sea of red taking over the city streets.

⭐ Why you should go: Don’t know your fellow riders’ names? No problem. You can take some inspiration from the Barbie movie and greet everyone with a simple, “Hi, Santa! Hi, Santa!” Plus proceeds benefit the Wisconsin Bike Fed, which does excellent cycling advocacy work.

TubaChristmas

🗓️ When and where it’s happening: December 13, 2026 (date tentative), Wisconsin State Capitol

📯 What it is: Celebrating its 53rd year, TubaChristmas is a worldwide phenomenon that gives tuba players of all ages and skill levels the chance to rehearse and publicly perform classic Christmas tunes together. The Madison event is particularly special and takes place in the State Capitol—the acoustics are incredible and you’ll have the chance to ascend to the tippy top of the building for magnificent views.

⭐ Why you should go: Hearing the sonorous echo of hundreds of tubas playing “God Rest Ye Merry Gentlemen” and “We Wish You a Merry Christmas” in the rotunda will be a gift to yourself that you may not have known you needed. Trust us on this one.

Do you have any other favorite Madison events? Let us know in the comments!

Pass the Snacks Adventures