This Underrated County Is The Perfect Road Trip From Chicago For Quirky Lakeside Towns

There's never a bad time to visit Chicago, and it has rightly earned a reputation as one of the best metropolises on the planet. In 2024, the Windy City came 16th on a list of the World's 100 Best Cities (per Resonance), finishing fourth within the United States, behind only New York, San Francisco, and LA. Chicago certainly has plenty to offer with incredible sights, great restaurants, a lively music and nightlife scene, and world-class galleries and museums. But visitors shouldn't confine themselves to the city on a vacation to the Midwest, because there is a wide range of places for a day trip within a few hours' drive from downtown. This goes double when the temperatures rise and you want to escape the heat of the city in the summer. Underrated Allegan County has the perfect mix of natural beauty, sandy beaches, and fascinating lakeside towns that make it worth loading up the car for a road trip getaway.

Allegan County sits on the opposite shore of Lake Michigan, and a visit from Chicago is a two-hour jaunt around the coastline, passing through Indiana and into Michigan. You're never far from water along the whole route, and there are plenty of good places to stop off if you want to make a longer trip, including some wonderful beach spots in Indiana Dunes State Park and National Park. Once you arrive in the largely rural Allegan County, it feels a world away from the hubbub and skyscrapers of Chicago. Here are some of its quirky highlights.

Although fairly modest in size with a combined population of around 2,300 people, Saugatuck and Douglas have developed a big reputation as one of the best lakeside destinations in the United States. While they may be separate cities, they go hand-in-hand as a hub of the "Art Coast of Michigan." Saugatuck actually came in second only to Stuart, Florida, in USA Today's 2024 poll of 10 best coastal towns in America.

Linked by a bridge across the Kalamazoo River, both towns are a stone's throw from the sandy shores of Douglas Beach Park and Oval Beach. Saugatuck Dunes State Park is also a great place to hike along Lake Michigan. In town, the area's status as a haven for artists and art lovers is well-founded with the Ox-Bow School of Art and the Armstrong De Graaf International Fine Art gallery, plus plenty of workshops, independent galleries, exhibitions, and festivals to browse. The laidback sister cities are also renowned for being a welcoming destination for LGBTQIA+ visitors.

As you'd imagine for such a pair of hip lakeside towns, there are no shortage of fashionable places to grab something to eat and drink. Several craft breweries have set up shop in the area, with some of them offering a food menu to compliment the range of beers. Saugatuck Brewing Company in Douglas serves up quality pub grub, while the vintage baseball-themed Mitten Brewing Company across the river fires up a selection of gourmet pizzas.

As some of the place names north of Saugatuck and Douglas suggest, there is a Dutch-American presence in Allegan County dating back to settlers arriving from the Netherlands in the mid-19th century. The city of Holland on Lake Macatawa proudly maintains its Dutch heritage, from its traditional architecture and Instagrammable flower fields at Veldheer Tulip Garden to the only fully operational Dutch windmill in the United States. The Dutch influence extends to the cuisine, with several restaurants serving up specialities like Metworst (pork sausage), balkenbrij (meatloaf) and lekkerbekje (deep-fried fish bites). It isn't all about the Dutch connection, however; there are beautiful Lake Michigan beaches to be found at Holland State Park, and the area is superb for outdoor adventures with many miles of hiking paths and bike trails. The proximity to water also makes it ideal for fishing and boat rentals.

While you're in Allegan County, it's also worth checking out Fennville. Situated a little further inland around a 10-minute drive from the beachcomber's paradise of Pier Cove Park, the small rural city attracts visitors with its scenic landscapes and burgeoning scene. Pick your own apples (and other fruit) at Crane Orchards while getting lost in the corn maze, sample the hand-made cheeses at Evergreen Lane Farm & Creamery, or simply kick back and enjoy the award-winning hand-pressed cider at Virtue Farm. Whatever you choose, a visit to these quirky lakeside towns is sure to leave you relaxed and pleasantly sated before returning to the city.