Watch Out For Rampaging Santas

The 2022 Santa Cycle Rampage on Prospect Avenue. Photo by Jeramey Jannene.

Do not let the below-freezing temperatures scare you away from leaving the house this weekend. There are holiday events that you’re not going to want to miss, as well as plenty of great, unique shopping opportunities for the upcoming holiday.

Hundreds, if not thousands, of bicycling Santa Clauses will descend upon Milwaukee as part of the annual Santa Cycle Rampage, and Brady Street will transform into a holiday market. WMSE is putting on its annual Big Band Grandstand fundraiser, and those who are tired of red-nosed reindeer can experience a different Christmas character at the Milwaukee Krampusnacht Acht.

December 6: Santa Cycle Rampage

This weekend, hundreds of Santas will trade in their sleighs for bikes as they cycle across the city to raise funds for the Wisconsin Bike Fed’s educational programming. The 13-mile slow ride will depart from Wheel & Sprocket’s Bay View location at 9:30 a.m. and will make a stop at Lakefront Brewery and other local businesses. Those who want to do a shorter version of the ride can register for the Elf Cycle Frenzy, a family-friendly ride that clocks in at 3.5 miles. To register for either ride, visit the Wisconsin Bike Fed’s website.

December 6: ‘Nutcracker! Magical Christmas Ballet’

Experience a holiday classic in a new way with Nutcracker! Magical Christmas Ballet. The traveling show will be in Milwaukee for one night at the Miller High Life Theater and features an international cast, eye-catching costume designs and life-like puppetry. The show will begin at 2 p.m. To purchase tickets, visit the Miller High Life Theatre’s website.

December 6: Santa’s Holiday Gift Market

Brady St. will transform into a holiday market, giving attendees the chance to shop goods from local artisans and makers while supporting local businesses in the area. The street will also be filled with carolers, and families can snap photos with Santa himself throughout the day. The event will also be collecting hoodies for donation to Cass Street School in an effort to help keep students warm this winter. Each donation grants a raffle ticket for a chance to win prizes. Santa’s Holiday Gift Market will run from 10 a.m. to 4 p.m. and is free to attend.

December 7: WMSE’s 11th Annual Big Band Grandstand

A Milwaukee holiday tradition, WMSE is celebrating its 11th year of the Big Band Grandstand – a fundraiser that supports the radio station’s studio and programming. The show will kick off with DJ set from WMSE’s Dewey Gill followed by the main event – a performance by multi-instrumentalist Gunhild Carling (also known as Sweden’s Queen of Swing) and her big band. The event also features a silent auction, where guests can bid on a variety of items. The Big Band Grandstand will run from 4 p.m. to 7:30 p.m. at Turner Hall Ballroom. To purchase tickets, visit WMSE’s website.

December 7: Milwaukee Krampusnacht Acht

Like The Nightmare Before Christmas, the 8th annual Krampusnacht Acht festival brings spooky vibes to the traditionally cheerful holiday. Celebrating the half goat, half demon Krampus, who punishes naughty children in Alpine folklore, the festival will bring live music, costumes, vendors and more to the Brewery District. Each business in the district will host its own activities, such as live bands at Best Place and tabletop gaming at Pilot Project. The American Ghost Walks Krampus Parade will depart at 7 p.m. and will traverse Juneau Ave. from 9th St. to 11th St. and back. Krampusnacht Acht is free to attend and will run from 3 p.m. to 9 p.m. For more information, visit the Milwaukee Krampusnacht website.

December 7: Handcrafted

If you still have some Christmas shopping to do, check out Lakefront Brewery’s Handcrafted market, where over 20 hand-selected vendors will sell artwork, crafts, home goods and more. The brewery will have its usual food and drink menu available as well as Bloody Marys. The event will also collect non-perishable foods for donation to Kinship Community Food Center. The market is free to attend and will run from 11 a.m. to 3 p.m. For a complete list of participating vendors, visit Lakefront Brewery’s website.