Madison Area Winter Bucket List

Your Guide to Seasonal Magic Around Dane County for the 2025-2026 winter season. Enjoy this Madison Area Winter Bucket List.

Winter in Wisconsin can feel slow or a little boring if you’re stuck in the same routine. From outdoor adventures to cozy indoor escapes, this winter bucket list is packed with ideas to shake things up and make the most of the colder months, whether you’re spending them with friends, family, or on your own.

#1 - Go Ice Skating at The Edgewater Hotel

Glide across the ice at The Edgewater Hotel’s outdoor rink! Surrounded by stunning lakefront views, ice skating here is a festive and fun winter activity for all ages.

#2 - Henry Vilas Zoo Lights

Henry Vilas Zoo Lights is an annual winter event in Madison, WI, where the zoo is lit with more than a million lights after hours. Visitors can walk through the grounds to see a mix of classic and animal-themed displays, explore the light maze, and take in a unique after-dark view of the zoo.

#3 - Go for a Winter Hike

Bundle up and hit the trails for a peaceful winter hike. Snow-covered paths, quiet forests, and crisp air make even familiar routes feel magical. Whether it’s a quick walk or a longer adventure, winter hiking is a refreshing way to enjoy the season’s beauty.

For an unforgettable view, try a winter hike at Devil’s Lake. The lake views are beautiful this time of year!

#4 - Try Skiing or Snowboarding

Hit the slopes this winter! Wisconsin has over 30 downhill ski and snowboard locations, perfect for thrill-seekers and beginners alike.

#5 - Plan a Cozy Cabin Getaway

There’s nothing better than gathering a group of friends and escaping to a cute winter cabin. Find a cozy Airbnb with a fireplace, pack your comfiest sweaters, and spend the weekend sipping hot cocoa, playing games, and enjoying a perfect winter reset (even better if it has a hot tub!).

#6 - Catch the Canadian Pacific Holiday Train

The Canadian Pacific Holiday Train is a festive, traveling event hosted by CPKC that features a decorated train with thousands of lights, live concerts, and the collection of food and money for local food banks in Canada and the U.S. The event is free, but attendees are encouraged to bring non-perishable food items or monetary donations.

It will be in south central Wisconsin December 9th - December 11 this year. They will be going through Watertown on Wednesday, December 10th from 8pm - 8:30pm. Click here to view all the dates/times here.

#7 - Explore the Cave of Lights

All December and January, Cave of the Mounds will be beautifully decorated with holiday lights and festive décor. Whether you celebrate Bodhi Day, Christmas, Kwanzaa, or anything in between, the sparkling displays are for everyone to enjoy.

#8 - Host a Cookie Swap & Holiday Movie Night

Invite over a few friends or family, swap your favorite cookies, pour some hot cocoa, and kick back with a holiday movie. Easy, cozy, and delicious!

#9 - Go to a Holiday Market

Stroll through a festive holiday market filled with lights, local crafts, and seasonal treats. It’s a great way to find unique gifts, enjoy holiday snacks, and soak in the festive atmosphere.

Click here to view a list of local markets

#10 - Make Your Own Seasonal Decor or Craft

Get crafty this winter! Make ornaments, paint mason jars, create a festive welcome mat, or build a snowman from socks and rice. Anything you can bring out year after year. It’s a simple way to add personality to your space and start a seasonal tradition.

Make the Most of Winter!

No matter how you choose to spend it, winter is full of opportunities to try something new, make memories, and enjoy the season. Use this list as a guide, mix in your own ideas, and make this winter one to remember.