Thousands of Biking Santas To Take Over Milwaukee’s Streets

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

There are plenty of ways to spread holiday cheer this weekend in Milwaukee. The Santa Cycle Rampage charity ride will see hundreds of Santa Clauses biking throughout the city for a good cause. The Historic Third Ward will host a tree-lighting ceremony, and Milwaukee Ballet is putting on its annual production of The Nutcracker.

December 5-8: ‘Black Nativity’

Langston Hughes’ Black Nativity returns for its 9th annual holiday production, telling the story of the Nativity through African American scripture, poetry, dance and music. The musical will run for five productions and will feature a post-show talkback. Black Nativity will run Dec. 5 at 7:30 p.m., Dec. 6 at 7:30 p.m., Dec. 7 at 2 p.m. and 7:30 p.m. and Dec. 8 at 2 p.m. at the Wilson Theater at Vogel Hall. For more information and to purchase tickets, visit the Black Arts MKE website.

December 6: Christmas in the Ward

Milwaukee’s Historic Third Ward is celebrating the holidays with an evening filled with baked goods, a tree-lighting ceremony, live entertainment and more. The event will kick off at 5 p.m. with a cookie sale, live reindeer and costumed characters in Catalano Square and s’mores roasting. At 6 p.m., Santa Claus will lead a tree lighting ceremony with musical support from the Bach Chamber Choir and Sarah Fierek. The event will wrap up at 8:30 p.m. with a 10-minute Light the Hoan holiday light show. For a full schedule, visit the Historic Third Ward’s website.

December 7: Santa Cycle Rampage

Dust off your Santa Claus suit, tune up your bike and get ready to raise funds for the Wisconsin Bike Fed’s K-8 and High School educational programs. The 12-mile slow-rolling bike ride will see more than 1,000 Santa Clauses starting at the Bike Fed HQ in Bay View and traveling throughout the city. This year’s ride also features a MKE Elf Cycle Frenzy – a family and kid focused three-mile ride. For more information and to register for the ride, visit the Wisconsin Bike Fed’s website. And be on the lookout for bonus stops.

December 7-24: Milwaukee Ballet’s ‘The Nutcracker’

Michael Pink’s The Nutcracker: Drosselmeyer’s Imaginarium received universal critical acclaim for its opening year, and now the production is back and promises even more magic than previous years. The production will feature dancers from the Milwaukee Ballet School & Academy and the Milwaukee Ballet Orchestra will perform Tchaikovsky’s iconic score live. The production will run through Christmas Eve at the Marcus Performing Arts Center. For a full schedule and to purchase tickets, visit the Milwaukee Ballet website.

December 8: WMSE’s 10th Annual Big Band Grandstand

WMSE 91.7FM celebrates the holidays every year with a silent auction and gala featuring a performance by Gunhild Carling, a master of the trombone, bagpipes, trumpet and more. The event will also feature a special DJ set by WMSE’s Dewey Gill. The silent auction will sell off Green Bay Packers tickets, a $1500 Film Buff package from Milwaukee Film, gift cards from restaurants and more. All proceeds from the Big Band Grandstand go towards supporting WMSE. For more information, visit the WMSE website.

December 8: Merry & Bright Market

Anodyne Coffee Roasting Co. is putting on its fourth Merry & Bright Market, featuring over 20 local vendors selling curated and handmade goods such as jewelry, home goods, candles and more at the roaster’s Walker’s Point location. Anodyne will offer coffee specials as well as its dual seasonal release of its Merry & Bright Blends. The market will also feature food from Tots on the Street. New to the Merry & Bright Market this year is an outdoor holiday market courtesy of Station 1846. That market will also feature local vendors as well as a visit from Santa and his reindeer. The Merry & Bright Market will run from 10 a.m. to 2 p.m. and the outdoor market will run from 11 a.m. to 4 p.m.