Featured Events
1. Stronger Drinks: A ‘Stranger Things’ Pop Up
ALL WEEKEND | THE SUGAR MAPLE
In celebration of the highly anticipated final season of “Stranger Things,” The Sugar Maple will be hosting a themed pop-up all weekend long. The pop-up will feature local artists, unique themed cocktails, specialty merch, food and more. This event is free to attend and a schedule of each day’s games and events is available on the event listing.
2. Holiday Drone Show
SATURDAY AT 5 P.M. | VETERANS PARK
Celebrate the holidays with by watching the sky light up with a fun drone show! This event is free to attend and family friendly. Hot chocolate will be available, but make sure you dress for the weather. Drone shows are quiet and sensory friendly, making this a great alternative to fireworks.
3. Candy Cane Course
SUNDAY FROM 9 A.M. TO 12 P.M. | ESTABROOK PARK
The annual Candy Cane Course 5K/12K is back with exclusive Christmas swag, a custom finisher metal, treats and more. 5K and 12K registration includes a custom bib, shirt and finisher medal. There is also a 1 mile race and a kid’s dash with special swag available. Registration is $30.98 for adults and $22 for kids.
Tell us who you’d pick to be a Betty this year!
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4. 10th Annual Black Nativity
ALL WEEKEND | WILSON THEATER AT VOGEL HALL
Black Nativity showcases the story of the Nativity through scripture, poetry, dance and song using an African American perspective. Presented by Black Arts MKE, the musical showcases many great local actors of color. Tickets are available for purchase online at $50 each.
5. Cache Cider 5-Year Anniversary
ALL WEEKEND | CACHE CIDER
Cache is celebrating five years as Milwaukee’s first cidery! They will have a selection of new ciders and wines, vintage ciders and anniversary merch for sale. There will also be live music across all three days including a set performed by Cache’s founder Ethan Keller.
6. Sugar & Spice Gingerbread Workshop
THURSDAY FROM 5:30 P.M. TO 7:30 P.M. | THE PFISTER HOTEL
Enjoy two hours of elaborate gingerbread decorating with the Pfister’s pastry team. A selection of candies, cereals and cookies will be available to make each gingerbread house completely unique. Hot chocolate, apple cider and coffee will be served throughout the event and a cash bar will be available. A take-home box will be provided to ensure your creation gets home safely. Each ticket is $30 plus $45 per gingerbread house kit bought with it.
7. TRUE Skool Fall 2025 Showcase Gallery
THURSDAY FROM 4:30 P.M. TO 7:30 P.M. | MILWAUKEE COUNTY HISTORICAL SOCIETY
TRUE Skool, Inc is Milwaukee’s center for transformative creative arts and hip hop culture. This year, their fall showcase is celebrating receiving the US Artist National Recognition Award for Creative Impact. The showcase will highlight music, media, visual art and dance. The showcase is family friendly and free to attend.
8. Historic Third Ward Merch Pop-Up
FRIDAY FROM 12 P.M. TO 6 P.M. AND SATURDAY FROM 12 P.M. TO 4 P.M. | BROADWAY PAPER
The History Third Ward Association is hosting a pop-up shop at Broadway Paper to sell a special limited-edition collection of their merchandise. The collection is the neighborhood’s first capsule collection and consists of caps, tee-shirts, crewnecks, can koozies, coffee mugs and more. All of the designs were created by local artist Whitney Nettles.
9. Oak Creek Christmas Market
FRIDAY FROM 5 P.M. TO 8 P.M. | DREXEL TOWN SQUARE
Brand new for 2025, Oak Creek is hosting a Christmas Market. Featuring over 50 booths, there will be a variety of shops, food and drinks. 1703 will perform live holiday music throughout the market as well.
10. O Soulful Night
SATURDAY AT 7 P.M. AND 9 P.M. | BAR CENTRO
Faith Hatch is blending classic Christmas tunes with smooth jazz to put a modern spin on holiday music. Hatch will be performing with John Stanford and Bryanna Hatch and Mitch Dalzin Geroge Ballesteros, Tael Estremera and Yanni Chudnow will be on instrumentals. Bar Centro will have a selection of specialty cocktails. Tickets are available online for $15 each. This event is 21+ only.
11. It’s a Naughty Christmas Adult Comedy, Magic and Burlesque Show
SATURDAY AT 7 P.M. AND SUNDAY AT 9 P.M. | BRUMDER MANSION
Comedians, magicians, burlesque, oh my! Two Brothers One Mind is hosting a night of fun at the iconic Brumder Mansion. Doors will open 30 minutes before the show to offer guests a chance to tour the mansion that once held a speakeasy owned by Al Capone’s gang. Tickets are available online at $31.60 each. This show is 18+ only and contains adult language and themes.
12. Holly Jolly Cabaret
SATURDAY AT 7 P.M. | CSZ MILWAUKEE
ComedySportz Garage is bringing together a group of AIP alums to perform holiday hits from the radio, musicals, parodies and movies. Tickets are available online for $15 each.
13. Milwaukee SantaCon 2025
SATURDAY FROM 4 P.M. TO 10 P.M. | DUKE’S ON WATER
Santa! I know him! It’s Christmas bar crawl time with SantaCon2025. Dress in your best Santa attire and enjoy holiday drink specials at some of Milwaukee’s best bars. A ticket gets you access into bars with no cover fee, exclusive specials, a free after party and a DJ at multiple stops. Tickets are available online for $20.38 each. This event is 21+ only.
14. Muppets Christmas Carol Drag Brunch
SUNDAY AT 2 P.M. | MILWAUKEE IMPROV
Everyone is doing a Christmas Carol right now, so why not make it extra fun? The most iconic muppets will be there with a drag queen twist. Guests are encouraged to wear costumes and join in on the holiday cheer. Tickets are available online and start at $32.39. This event is 21+ only.
15. Brewery District MKE Locally Made Art & Craft Pop-Up
SUNDAY FROM 11 A.M. TO 3 P.M. | HISTORIC PABST BREWERY
Shop local this holiday season and support artists. The market will feature 14 vendors with a variety of goods including baked goods, accessories, body care, candles and more. Admission to the pop-up is free and a cash bar will be open inside the Great Hall. Each purchase goes directly to the artist.
