New Year’s week always lands a little sideways. Half the city is outside on purpose, the other half is hunting for warm rooms with good sound. This is not a big, flashy week. It is a good one if you pick carefully.

I have a tradition of riding my bike with friends to the Polar Bear Plunge at Milwaukee’s Bradford Beach. We watch the plungers! We don’t jump in! That’s crazy!

Bundle up and watch the lakefront do its winter flex. Giant kites, snow carving, and crisp new-year air.
https://www.visitmilwaukee.org/event/39th-cool-fool-kite-%26-snow-carving-festival/4203/

If you still have not done the lights walk, this is the final lap. Cocoa helps.
https://county.milwaukee.gov/County-Events/Milwaukee-Holiday-Lights-Festival

Warm up inside and make something with your hands. Low pressure and quietly satisfying.
https://mam.org/events/event/drop-in-art-making-kohls-art-studio/2026-01-02/

Paint alongside a local artist and add to a collaborative mural. Strong “start the year creating” energy.
https://mam.org/events/event/mural-painting-winter-break-fun/2026-01-02/

Serious jazz in a tight Riverwest room. Winter makes this kind of show hit harder.
https://centrocaferiverwest.com/events/2026-01-02/

Loud, local, and exactly the right amount of feral for a first Friday.
https://www.cactusclubmilwaukee.com/events/interlay-poolish-edging-chapped-lips/

First matches of 2026, starting off with a bang! Fast improv, dumb-smart jokes, and a crowd ready to laugh at anything.
https://www.facebook.com/ComedySportzMilwaukee

Zero-proof drinks, still social, no lectures. A solid daytime option.
https://www.cooperagemke.com/upcoming-events/na-day-a-dry-january-beverage-festival

Round two for the mural series. Paint a little, then find a hot drink.
https://mam.org/events/event/mural-painting-winter-break-fun/2026-01-03/

Quick, nerdy, and surprisingly calming. Windhover Hall always helps.
https://mam.org/events/event/architecture-and-highlights/2026-01-03/

You know these guys! A beloved Milwaukee power-pop band from the 90s, The Mosleys play a distinctive blend of poppy folk-rock with countrified and classic rock leanings, featuring catchy melodies, smooth vocals, and solid guitar work, often compared to classic power-pop but with a unique Milwaukee charm, making them a “best band to ever come out of Milwaukee” for many fans.Roots-forward set in a room that feels like a neighborhood living room.
https://centrocaferiverwest.com/event/the-mosleys/

Stacked DIY bill in a room that rewards showing up early and staying late.
https://www.cactusclubmilwaukee.com/events/magnetic-minds-exit-statements-plant/

Pop bangers, sweat, and the Planet doing what it does best.
https://www.mad-planet.net/events/2025/8/16/charli-amp-chappell-drag-show-amp-dance-party

Start the year feeling heroic or humbled. Possibly both.
https://runsignup.com/Race/WI/Milwaukee/TimeTravelHalfMarathonand5k10kMilwaukee

One last chance to contribute before the series wraps.
https://mam.org/events/event/mural-painting-winter-break-fun/2026-01-04/

Game-day energy, punk at halftime, and a room full of yelling that feels friendly.
https://www.cactusclubmilwaukee.com/events/milwaukee-record-halftime-show-chinesetelephones-2-2-2-2-2-2-2/

An easy culture hit without committing your whole Sunday.
https://mam.org/events/event/architecture-and-highlights/2026-01-04/

No bar, no small talk. Just move and let your brain rest.
https://www.eventbrite.com/e/ecstatic-dance-tickets-1977617017736

Monday shows are for the real ones. Small room, big sound, zero regret walk home.
https://www.cactusclubmilwaukee.com/events/no-thanks-to-you-bowvee-the-percipitators/

Free party energy with skate-shop DNA. DJs, drink specials, and people who actually dance.
https://www.cactusclubmilwaukee.com/events/sky-high-night-21-2/

A weekly classic. Smooth tracks and friendly chaos that makes Tuesday feel fake.
https://themiramartheatre.com/events/rb-tuesdays/

Bring a project or just show up. Craft night as winter survival strategy.
https://www.cactusclubmilwaukee.com/events/cbc-jan7-2026/

https://mam.org/events/event/thursday-nights-at-mam-2025-03-20-2026-01-08/

https://www.cooperagemke.com/upcoming-events

https://mam.org/events/calendar/category/featured/

Early January is where Cactus Club thrives. The holiday rush clears out, the room breathes, and the calendar fills with loud local bills, DJ nights, craft meetups, and community-first energy. If you only pick one place to keep showing up this week, this is it.

https://cactusclubmilwaukee.com