Driving Time: 2 hours, 7 minutes
Total Distance: 94.5 miles

Visit Harbor Country once, the southwest region of Michigan, and you’ll be hooked for life. The region that is so picturesque and crowded in the summer months gets a little sleepier when cold weather rolls around. But that’s when the fun can truly begin. Avoid heavy crowds, take in Michigan’s winter wonderland, and experience some of the area’s best indoor and outdoor spots in the “off season.”

Snowshoe in Warren Woods State Park, Three Oaks

This natural area can be quiet even in the height of summer, a refuge for people who enjoy being among the tall trees and virgin hardwoods. The easy two-mile path through the woods is perfect for snowshoeing – and it’s dog friendly so make sure to pack for Fluffy, too. Start in the morning after a fresh snow. You can get an early breakfast at many beloved eateries within a short driving distance, including the Early Bird Eatery, Froehlich’s, and Viola Café.

Box Factory for the Arts, St. Joseph

After your refreshing hike, drive north to St. Joseph, home of the iconic North Pier Outer Lighthouse (which is stunning when encased in ice). Visit the Box Factory for the Arts, a labyrinth of art galleries and professional businesses. It’s perfect for one of those damp, cloudy winter days, though enjoyable anytime you visit.

Ice Breaker Festival, South Haven

If you time it well, you can stop in at the Ice Breaker Festival in South Haven. The event takes place for three days in early February and features ice sculptures, chili, food and drink specials, cardboard sled race, and frozen fish fling. The shops of downtown South Haven also offer hot deals to welcome visitors. Fun for the whole family – how many people can say they’ve flung a frozen fish?

Echo Valley, Kalamazoo

Ready for a little more activity? Echo Valley is the region’s premier winter sports park. Thrill-seekers can check out the tobogganing run, where you can reach speeds up to 60 miles an hour. Tubing can be a fun family or group activity and sure to create some great memories. Warm up in the lodge afterwards. Visit nearby Brookside Park back in Otsego for a less intimidating sledding hill if you have younger children.

Lake Michigan Shore Wine Trail, Varies

During your drive, you’ve passed several wineries on the Lake Michigan Shore Wine Trail, and you can make a stop at any of them along your journey. Top off a fun-filled day (or weekend) with a glass of Michigan wine. The nearest wineries to Kalamazoo are Lawton Ridge Winery (open 12-6 and closed on Tuesdays), Cody Kresta Vineyard and Winery (Friday-Sunday, 12-6), and St. Julian Winery (open daily). Check the websites for additional information, including special events. Most wineries are fine with hosting younger guests.