It’s gotten cold out there this AM. 3 degrees as I started this newsletter! Winter in Milwaukee always walks the line between cheerful and chaotic — and honestly, that’s when the city feels most alive. This week brings two of our strangest, warmest, most beloved December traditions, plus a full slate of concerts, theater, and downtown glow.
⭐ Featured Events of the Week (Don’t Miss These)
🎅 Santa Cycle Rampage — Saturday, December 6 — Citywide
Milwaukee’s biggest costumed bike ride returns, and it’s exactly as festive and joyful as it sounds. Thousands of riders Santas, elves, reindeer, gingerbread men, grinches, full sleigh crews all roll through the streets in a city-wide wave of red fabric, bells, and questionable holiday leggings stopping at bars, breweries and restaurants all in support of the Wisconsin Bike Feds mission to promote year ‘round cycling.
Expect neighborhood cheering, impromptu bar stops, and a level of bike-powered cheer that somehow warms the whole city even when the air hurts your face.
Saturday’s weather is looking like mid 20’s so dress appropriately!
Greg and Tony a few years back on Santa Rampage. It will be colder this year!
Milwaukee Krampusnacht Acht — Sunday, December 7 — Brewery District
Krampusnacht returns to its outdoor festival roots in the Brewery District — a perfect pairing of historic brick, winter darkness, and roaming horned creatures.
This isn’t just a walk-through: it’s fire performers, folklore characters, a European-style winter market, artisan vendors, live music, food, drinks, and the annual Krampus parade weaving straight through the crowd.
Think “holiday festival,” but darker, louder, and far more fun than it has any right to be. A perfect “dat after the Rampage” party!
📅 This Week in Milwaukee December 4–10, 2025
Thursday — Dec 4
A Christmas Carol @ Pabst Theater — 7:00 PM
Opening weekend of Milwaukee’s annual holiday tradition — warm red velvet, flickering lights, and all the nostalgia you expect.
Friday — Dec 5
Lefty Luci 3rd Anniversary Show and Ed’s Birthday @ Sabbatic — 9:00 PM
Lefty Luci celebrates 3 years of doing Lefty Luci stuff and Ed celebrates (significantly) more than 3 years of doing Ed stuff.Joined by: M545, Anti-Everything (Kenosha), Resurrectionists
Sabbatic shows are always free, take care of the bartenders and plan to buy some merch from the wicked cool bands that are playing.
👉 https://www.facebook.com/events/703893336099387/Harry Potter and the Sorcerer’s Stone In Concert @ Riverside Theater — 7:30 PM
Live orchestra + big screen = pure wizarding comfort.
A Christmas Carol @ Pabst Theater — 7:00 PM
Classic, cozy, deeply Milwaukee.
Saturday — Dec 6
Santa Cycle Rampage — 9:30 AM and rolling all day
Citywide bike-costume madness as featured above.
A Christmas Carol @ Pabst Theater — 2:00 PM & 7:00 PM
Matinee or nighttime glow — both hit the holiday sweet spot.
Harry Potter and the Sorcerer’s Stone In Concert @ Riverside — 7:30 PM
Second night of musical movie magic.
Sunday — Dec 7
Milwaukee Krampusnacht Acht — Brewery District — 3:00 PM–9:00 PM
Fire, folklore, market stalls, music, and Milwaukee’s wildest winter crowd.
Harry Potter and the Sorcerer’s Stone In Concert @ Riverside — 2:30 PM
A dreamy Sunday matinee with full orchestra.
A Christmas Carol @ Pabst Theater — 12:00 PM & 4:30 PM
Bring the family or go solo — it still lands.
Monday — Dec 8
MSO Mondays @ Colectivo — daytime
Free chamber music in a neighborhood café — the softest way to start a winter week.
Tuesday — Dec 9
A Christmas Carol @ Pabst Theater — 7:00 PM
Theatrical holiday comfort, midweek edition.
Wednesday — Dec 10
WEDMKE (Free) @ Turner Hall Ballroom — evening
Arts, performance, and a casual downtown hang — always worth dropping in.
🔭 Looking Ahead
Holiday Pops @ Bradley Symphony Center — Dec 13–21
Big orchestra, bells, choir — Milwaukee’s shiny seasonal centerpiece.
Mannheim Steamroller Christmas @ Riverside — Dec 21
The legendary Christmas-rock spectacle returns.
The Commercialists play A Charlie Brown Christmas @ Turner Hall — Dec 23
Local jazz magic + holiday nostalgia = automatic annual tradition.
Forward this to someone who loves Milwaukee at its best.
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