Even though autumn technically ended a few weeks ago, it’s finally beginning to set in: winter is actually here. The holidays are over and we’ve already had a little bit of snowfall. And there’s still more than two months of this ahead! With that in mind, we thought you might appreciate a listing of local festivals, conventions, outdoor block parties, and family-friendly events taking place in and around Milwaukee this winter. Get out there and face cabin fever head-on at some of these events. We’ve got this, Milwaukee!

Friday, January 12 and Saturday, January 13
Goblin King Masquerade Ball @ Turner Hall
Awkward Nerd Events will once again transform Turner Hall Ballroom into a magical world of fantasy. There will be themed cocktails and mocktails, performances from The Goblin King Players, a custom curated drag show, and more during this two-night event.

Sunday, January 21
Winterfest @ Boerner Botanical Gardens
Head over to “Milwaukee County’s Living Museum” and cure your winter blues at Boerner Botanical Gardens’ Winterfest. From 10 a.m. to 2 p.m., attendees can partake in indoor activities, guided winter walks, live music, free hot cocoa, and more seasonal fun in nearby Hales Corners.

Saturday, January 27
Ice Bear Fest @ Third Space Brewing
Third Space Brewing’s Ice Bear Fest returns! From noon to 5 p.m., the Menomonee Valley brewery will host “an epic ’80s Après ski party” in its beer garden to celebrate its tasty seasonal Baltic porter. In addition to the abundance of Ice Bear on hand, the winter affair will feature DJs and a live band playing ’80s jams, food trucks, shotskis, and various other Third Space brews.

3rd Annual Bluegrass Winter Heater @ Anodyne Walker’s Point Roastery
Though it’s happening in the dead of winter, the Bluegrass Winter Heater will make Anodyne’s Walker’s Point Roastery warm and toasty with tunes from a phenomenal foursome of great bluegrass bands. The third annual affair will feature performances by The Spooklights (formerly MK Ultra), Dig Deep, Valley Fox, and a headlining set from The MilBillies from—you guessed it!—Milwaukee.

Lynden Winter Carnival @ Lynden Sculpture Garden
From 10 a.m. to 4 p.m. on January 27, Lynden Sculpture Garden will host a day of outdoor activities for the whole family. Lynden Winter Carnival will include “art-making, scavenger hunts, tree-walks, workshops, and whatever other winter activities—ice skating, painting the pond, cross-country skiing, snowshoeing—the weather permits.”

Saturday, February 3
Mitten Fest @ Boone & Crockett
Mitten Fest is a sprawling block party that offers a one-day escape from the seasonal doldrums. Over its 10-year run, it’s earned the undisputed distinction of being Milwaukee’s favorite wintertime celebration. We’re pleased to report Mitten Fest will be returning for another installment in early 2024. However, there will be one noticeable change. On Saturday, February 3, Mitten Fest 2024 will take place outside Boone & Crockett (818 S. Water St.) a few miles up the road in the Harbor District. The venue change is a temporary one, as Burnhearts ownership wanted to take a year away from hosting the ever-growing block party “to re-envision [their] location.” It’s going to be the same great event, only in a new location this time around. Stay tuned for the music lineup and more information as Mitten Fest nears.

Great Lakes Pet Expo @ Wisconsin State Fair Park
While there are a bunch of expos, tournaments, and trade shows scheduled to take place at Wisconsin State Fair Park this winter, the Great Lakes Pet Expo is the best of the bunch. (No offense, Milwaukee Boat Show!) The 19th installment will bring thousands of animal lovers to Wisconsin State Fair Park to explore 143,000 square feet worth of “pet loving shopping and services, entertainment, educational experiences, and some of Wisconsin’s cutest adoptables.” Get out of the house, bring the whole family, and support Wisconsin’s homeless companion animals.

Sunday, February 4
MKE Chili Bowl @ Potawatomi Hotel & Casino
The mighty MKE Chili Bowl is back to tickle tongues, clear sinuses, and bring a wide variety of Milwaukee-area culinary professionals together to compete for The Golden Ladle. Head to Potawatomi Hotel & Casino on Sunday, February 4 to sample traditional, spicy, and vegetarian chili varieties.

Saturday, February 10
Milwaukee Comic Con @ Wisconsin State Fair Park
Behold! Dozens of comics, collectibles, characters, and more will be on hand at the Wisconsin State Fairgrounds on February 10 during the Milwaukee Comic Convention.

Saturday, February 10 and Sunday, February 11
Brick Fest Live @ Wisconsin State Fair Park
Calling all bricklayers! The Brick Fest Live tour will make a stop in West Allis for two days of block-based fun for all ages. There will be “over a million blocks on display and ready for play” at Wisconsin State Fair Park, including life-size models, hands-on attractions, and rare Lego merchandise. Block off your weekend for Brick Fest Live.

Friday, February 23 through Sunday, February 25
Flat Out Friday @ Fiserv Forum and Mama Tried @ The Rave / Eagles Ballroom
If you’re somehow unfamiliar, Flat Out Friday features motorcycle racers riding on top of a track that’s slathered in Dr. Pepper syrup and it’s awesome! This event is just one part of the Mama Tried festivities that are slated to happen at various local spots in mid-February. The Mama Tried Motorcycle Show itself will take place at The Rave February 24-25.

Sunday, February 25
Milwaukee’s Best Bloody 2024 @ Italian Community Center
On February 25, the 12th annual Milwaukee’s Best Bloody contest will find bartenders showcasing their signature bloody marys at the Italian Community Center while vying to have their cocktail concoction crowned, well, Milwaukee’s Best Bloody. As if the opportunity to try a bunch of bloodies and cast your vote on your favorite one isn’t enticing enough on its own, proceeds from the event “support Great Lakes Hemophilia Foundation in their mission to educate, support and advocate for the Wisconsin bleeding disorders community.”

Wückfinter @ Ray’s Wine & Spirits
Prepare to wage war on the winter doldrums outside of Ray’s Wine & Spirits in late February. From noon to 5 p.m. on Sunday, February 25, the event—which is an exclusively outdoor affair—will allow patrons the chance to indulge in tons of 3 Floyds beer (including some rarities TBA) and a one-day-only 3 Floyds boozie slushie. Beyond the beer offerings, Ray’s parking lot and parts of 89th Street and 90th Street will host an impressive cast of food vendors and a DJ-curated playlist. It’s going to be a Wücking awesome day in the Rayborhood.

Bacon Fest MKE @ Potawatomi Hotel & Casino
On Sunday, February 25, The Hog and Potawatomi Hotel & Casino will host another installment of Bacon Fest MKE. The 12th annual celebration of pork products will feature an abundance of vendors serving up their finest swine to a hungry horde of bacon aficionados. Come to Potawatomi on February 25 and pig out.

Friday, March 8 through Sunday, March 10
Anime Milwaukee @ Hilton Milwaukee City Center Hotel
What started as a college anime club meeting has blossomed into a massive three-day convention that annually brings hundreds of folks to the Hilton in Downtown Milwaukee to celebrate “anime, manga, Asian culture, music and gaming.”Anime Milwaukee will make its in-person return March 8-10.

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.