Chill Destinations and Cool Road Trips for Festive Winter Break Fun

Dec 22, 2021

Huzzah, winter break is here! We’re ready to kick back, relax, and celebrate the holiday season with our favourite people. And what better way to do just that, than with a plethora of fun destinations to check out during your time off! Whether you’re enjoying these activities with family or friends, we know you’re going to round out 2021 on a high note.

Just because the winter weather is here doesn’t mean you can’t enjoy the great outdoors and hiking trails in the area. Hang up those hiking boots and swap them out for some snowshoes and skis! On less than a tank of gas you’ll be on your way to winter wonderland bliss. Feeling the crunch of the fresh snow under your feet, enjoying the brisk fresh air and that “it’s going to snow any moment now” scent on the breeze. There’s nothing else quite like it!

Local Places for Snowshoeing, Sledding, and Cross Country Skiing

For those with a need for speed, you can swap your street racing energy for a set of downhill skis. Forget the gravel flying beneath your spinning wheels on the road, and get ready for clouds of fresh powder and blustery swirls of snow. We’ve got the best picks in the area for mountain downhill skiing, snowboarding, snowtubing and more. Check out our picks for best Ski and Snowsports Areas & Resorts worth the road trip!

Best Downhill Skiing and Winter Sports Destinations

If you’re not much for nature or winter sports, that doesn’t mean you’ll be left out in the cold for winter break fun! You can head into the city for a night out on the town, enjoy some winter festivities like Ice Skating or Sledding, and other nifty ideas. So check out our list for non-sports related winter destinations, and some unconventional holiday celebrations. Start a new tradition with your loved ones this year, and live life to the fullest!

Wintertime Fun for Everyone

Looking to spend the break with quiet respite instead of being constantly on the move? You’ll find all the rest and repose you’re craving on our Midwest Winter Getaways list. We’ve found everything from charming cottages to log cabin retreats, so no matter your flavor or passion, you’ll have a blissful stay.

Quiet Weekend Getaways

If you prefer the staycation route, there’s also lots of fun things to do right here in Waukegan! Check out our many local restaurants, cafes, and small businesses. And let us know if you have a recommendation for a nearby activity, recommended accommodations for cozy winter getaways, and we may just feature it in an upcoming post!