Ultimate Milwaukee Winter Bucket List {FREE PRINTABLE!}

milwaukee winter 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 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 Bucket List

  1. Go ice skating! 
  2. Indulge in your favorite holiday drink! Visit Starbucks for a Peppermint Mocha or try a sweet winter-themed creation at Fiddleheads or Stone Creek Coffee to ring in the cold season!
  3. 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 chair lifts and gentle or more challenging slopes; private and group lessons are available.
  4. Pick a winter festival to go to; some fun ideas are US National Snow Sculpting ContestWaukesha Janboree, or Mittenfest!
  5. Sip some wine or beer at County Clare Fireplace. County Clare’s offers the perfect ambience for those cold, snowy date nights. Enjoy dinner, stay for drinks!
  6. Check out 3rd Ward’s Annual Christmas Festival offering lights, music, cookies, hot chocolate, Mrs. Claus and her reindeer, fireworks, Trinity dancers and more!
  7. Love Dogs? Enjoy a family favorite dog sledding at Whitnall park! 
  8. Have chapped lips during the winter? Take a tour of the Carmex factory to learn more about them!
  9. Looking for a free activity? 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!
    Ready to ski!

    Ready to ski!

  11. Sit back, let the kids gorge out on candy and popcorn, and watch Elf or another holiday fave 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 Milwaukee tradition and see The Christmas Carol at the Pabst Theatre! Make it a girls night! 
  15. Plunge into the lake as part of the Polar Bear Plunge
  16. Check out the Winter Carnival at Schlitz Audubon Nature Center. Snowshoeing and cross country skis are also welcome on the trails!
  17. Attend a holiday show in the Mitchell Park Show Dome
  18. Visit Kopps for a scoop of one of their special seasonal flavors. 
  19. See the holiday lights show at Miller Valley. 
  20. Watch Santa light the tree at the Pfister on November 25th. 
  21. Breakfast (or lunch) with Santa at the zoo
  22. Have a Build-A-Snowman contest with the kids in your neighborhood! 
  23. Run or walk in the annual Jingle Bell Run 5K!
  24. Dust off your bike and take part in the annual Santa Cycle Rampage.
  25. Treat yourself to an afternoon tea at the Pfister surrounded by panoramic views of Milwaukee and Lake Michigan. 
  26. Invest in yourself, learn a new skill and create something new by taking a class through Milwaukee Rec.
  27. Visit Organ Piper Pizza for dinner out and to listen to some holiday tunes. 
  28. Bundle up and walk through Candy Cane Lane to view the holiday lights…or drive! 
  29. Enjoy carolers, cocoa and Christmas lights on Downer Avenue
  30. Take the family on a new adventure and cut down your own Christmas tree
  31. 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.
  32. Take a brewery tour of Sprecher, great for parents and kids! 
  33. Learn how to curl
  34. Don’t miss out on the Holiday Train that is returning to Milwaukee this year!
  35. Enjoy a full day of holiday programs and activities while strolling the streets of Old Milwaukee decked out in holiday splendor. 
  36. Try ice fishing
  37. Visit Enchantment in the Park! Bring a date, plan a girls night, or head out with the kids!
  38. Work up a sweat rollerskating with the family at St. Pius X on a Saturday night.
  39. Go sledding! 
    Bundle Up and Stay Warm!

    Bundle Up and Stay Warm!

  40. Give back to the community by participating in a service project with the family. 
  41. Check out Holiday Pops, a bright holiday show put on by the Milwaukee Symphony Orchestra. 
  42. Have a date night and see Milwaukee Ballet Company’s production of The Nutcracker
  43. Nothing spreads Christmas cheer like a symphony of animatronic bears playing Christmas music in the middle of the Shops at Grand Ave. 
  44. Host an Ugly Christmas Sweater party!
  45. Head to story time in the rooftop tipi at Urban Ecology!
  46. Plan a girls night at Music Under Glass at the Domes
  47. Go cross country skiing at Grant Park! 
  48. Let the kids experience Harry Potter in a different way with Milwaukee Symphony Orchestra! 
  49. Bake cookies on a snowy afternoon with the kids! 
  50. Write a letter to Santa! 

To make things even easier for you to check out all these fun Milwaukee activities, we’ve made a PRINTABLE Milwaukee Winter Bucket List! Show off your winter fun by using #mkembwinter on Instagram. 

>>> Click here for the Free Printable! <<<

What fabulous activities would YOU add to this list? 

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