Ultimate Milwaukee Winter Activities and Bucket List


Winter in Milwaukee is a magical place, no matter how cold it may be! The holiday lights make the streets come to life and it’s almost like the air smells of hot cocoa. This year’s bucket list of Milwaukee winter activities offers 50 ideas of things to do this winter for every budget, interest, and age. We’ve even included some fun ideas for date nights as well as for when you get together with the girls. Think you’ve done it all in Milwaukee, think again! (Please note to check each event/business website for the most up to date information.) 

The Ultimate Milwaukee Winter Activities Bucket List

Milwaukee Winter Activities

  1. Go ice skating! In Milwaukee, you can go indoors at the Pettit National Ice Center or head outdoors using our Outdoor Ice Skating guide!
  2. Would you rather watch someone else ice skate? Check out a Milwaukee Admirals game at the US Cellular Arena! When they’re on the road, the Milwaukee Wave play there too!
  3. Indulge in your favorite holiday drink! Visit Starbucks for a Peppermint Mocha (YUM!) or try a sweet winter-themed creation at Fiddleheads or Stone Creek Coffee or your favorite local coffee shop to ring in the cold season!
  4. Enjoy skiing, snowboarding or the largest tubing park in the world at Sunburst! Whether you’re a seasoned pro or new to skiing, Sunburst offers a fun range of options for your whole family. Enjoy the chairlifts and gentle or more challenging slopes; private and group lessons are available.
  5. Pick a winter festival to go to; some fun ideas are US National Snow Sculpting Contest or Waukesha Janboree!
  6. Sip some wine or beer at County Clare Fireplace. County Clare’s offers the perfect ambiance for those cold, snowy date nights. Enjoy dinner, stay for drinks!
  7. Check out Third Ward’s Annual Christmas Festival offering lights, music, cookies, hot chocolate, Mrs. Claus and her reindeer, fireworks, Trinity dancers and more!
  8. Love Dogs? Enjoy a family favorite Milwaukee winter activity – dog sledding at Whitnall park (snow permitting, of course)!
  9. Looking for free Milwaukee winter activities? Walk the lakefront and take a look at how beautiful the waves are as they crash into ice and the beach.
  10. Have fun outdoors doing something other than sledding and tubing! Try snowshoeing for a new adventure!
  11. Sit back, let the kids gorge out on candy and popcorn, and watch Elf or another holiday classic during a snowy day!
  12. Enjoy the Pabst Mansion during the winter for their annual dinner and show!
  13. Grab your mittens and your date to enjoy a romantic tour of DTWN MKE by horse drawn carriage!
  14. Take part in a 40+ year traditional Milwaukee winter activity and see The Christmas Carol at the Pabst Theatre! Make it a girls night!
  15. Take in a movie at a Marcus Cinema. With new locations like the Movie Tavern and BistroPlex, there are new ways to have the movie going experience
  16. Check out the Winter Carnival at Schlitz Audubon Nature Center. Snowshoeing and cross country skis are also welcome on the trails!
  17. Attend the holiday floral show in the Mitchell Park Show Dome. (Remember that the first Thursday of the month is free for all Milwaukee County residents! Did someone say playdate!?!
  18. Visit Kopps for a scoop of one of their special seasonal flavors. Our favorite is Sugar Plum Fairy – blackberry strawberry custard dolloped with marshmallow clouds and sparkling jewels of sugar!
  19. See the holiday lights show at Miller Valley.
  20. Watch Santa light the tree at the Pfister on November 29th.
  21. Breakfast (or lunch) with Santa at the zoo!
  22. Watch Harry Potter or Home Alone with music from the Milwaukee Symphony Orchestra live!
  23. Have a Build-A-Snowman contest with the kids in your neighborhood!
  24. Grab your sneakers and run or walk the Jingle Bell Run with your jingle bells on!
  25. Dust off your bike and take part in the annual Santa Cycle Rampage. Join the hundreds of Santas (and elves) who take to the street on two wheels (instead of sleighs) to celebrate the holidays in style! This is a slow paced 5.4 mile ride. Children are welcome to ride along.
  26. Treat yourself to an afternoon tea at the Pfister surrounded by panoramic views of Milwaukee and Lake Michigan.
  27. Invest in yourself, learn a new skill and create something new by taking a class through Milwaukee Rec.
  28. Visit Organ Piper Pizza for dinner out and to listen to some holiday tunes.
  29. Bundle up and walk through Candy Cane Lane to view the holiday lights…or drive!
  30. See Elf or A Winter’s Tale at First Stage Milwaukee
  31. Take the family on a new adventure by incorporating a new Milwaukee winter activity this year – cut down your own Christmas tree!
  32. Handel’s glorious Messiah returns once again to the MSO. Experience some of the most beautiful sacred music ever written with conductor Ben Gernon, world-class musicians, the Milwaukee Symphony Chorus and acclaimed guest soloists.
  33. Take a brewery tour of Sprecher, great for parents and kids! Reservations are required for all tours.
  34. Learn how to curl!
  35. Enjoy a full day of holiday programs and Milwaukee winter activities while strolling the streets of Old Milwaukee decked out in holiday splendor.
  36. Visit Enchantment in the Park! Bring a date, plan a girls night, or head out with the kids!
  37. Work up a sweat rollerskating with the family at St. Pius X on a Saturday night.
  38. Find a hill and go sledding!
  39. Give back to the community by participating in a service project with the family.
  40. Have a date night and see Milwaukee Ballet Company’s production of The Nutcracker.
  41. Host an Ugly Christmas Sweater party!
  42. Head to story time in the rooftop tepee at Urban Ecology!
  43. Go cross-country skiing at Grant Park!
  44. Holiday Pops by the Milwaukee Symphony Orchestra is Milwaukee’s favorite holiday musical tradition. Tony DeSare joins the Orchestra to perform classics, carols, and more. Milwaukee Handbell Ensemble rings in the holiday season!
  45. Bake cookies on a snowy afternoon with the kids! Try a recipe or two from the WE Energies Cookie Book!
  46. Write a letter to Santa!
  47. Have the family get in their jammies and head to the Country Christmas lights display at the Ingleside Hotel!
  48. Let the kiddos go crazy with glitter and glue to make some ornaments for your tree and even send some to a local nursing home to bring the residents some cheer!
  49. Perfect your favorite soup or stew recipe while you watch the snowflakes fall!
  50. What is better than cookies? Enjoying some cookies with the “big guy” himself! MKE Moms Blog is throwing our third Cookies with Santa Holiday Celebration!

Show off the fun you have with these Milwaukee winter activities by tagging us @milwaukeemoms on Instagram.

What fabulous Milwaukee winter activities would YOU add to this list?

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