3 Small Towns in Michigan So Dreamy, You’ll Swear You’ve Seen Them on TV

When I was growing up in Chicago, Michigan was always on the radar for a weekend trip or summer vacation. Its stunning nature and many communities with small-town charm were and remain a welcome retreat from the chaos of living in a big city. No matter the time of year, there are seemingly endless dreamy small towns in Michigan that are worth putting on your Midwest bucket list. I'll highlight a trio of my favorites.

1. St. Joseph

Located in the southwest part of the state, St. Joseph is one of my favorite places to visit year-round. In the summer, it often feels reminiscent of an episode of The Summer I Turned Pretty. The community is dotted with beautiful beachfront homes and ice cream parlors that evoke childhood nostalgia for everyone who passes by.

Last summer, I got to attend one of the town's weekend antique car shows, and it felt as if St. Joseph had transformed into a scene from Leave It to Beaver. I’ve also enjoyed visiting during the cooler months. The area is home to many great wineries, including the Lazy Ballerina Winery, where I visited on a girls’ trip. St. Joseph is truly a picturesque little town, perfect for getting away and enjoying classic rest and relaxation.

2. Holland

By pure happenstance, I attended a college in Chicago that had deep ties to Dutch-American history. As a result, I made many friends who were from Holland, Michigan. This community is filled with classic Dutch architecture that makes you feel like you’ve stepped into the Netherlands.

The area is perhaps most famous for its annual Tulip Time Festival. This festival celebrates the more than five million tulip bulbs that sprout in the springtime. Visitors will notice the many large traditional Dutch windmills that pop up around the community and throughout the tulip fields. If you’re looking for a little Euro-adventure without the cost of the plane ticket, Holland is a great dupe for starring in your own romantic comedy. Although you may recognize the name of the town from Nicole Kidman’s 2025 thriller, Holland—quite a different vibe than that of the actual community!

3. New Buffalo

Another fantastic beach town that still shines in the winter is New Buffalo. Just over an hour drive from downtown Chicago, Grand Beach is filled with things to do. Grab a meal at the iconic Stray Dog Bar & Grill or indulge in a sweet treat from Oink’s Chocolate Pig. During the summer bbfs months, New Buffalo Beach is 800 feet of Caribbean-level paradise. Like St. Joseph, New Buffalo still has plenty to offer in the winter, like exploring the surrounding distilleries and wineries, utilizing the Nordic ski trails, and sledding.  

No matter the time of year, each of these dreamy small towns in Michigan shines. Between beachfront adventures and cozy winter winery tours, Michigan continues to have something for everyone at all times of the year. Feeling inspired? Try planning your own Michigan trip using Only In Your State’s itinerary planner.