The storybook village of Saugatuck is less than three hours from Chicago but feels as though it’s a thousand miles away. Its proximity has made the area a summertime destination for Chicagoans since The Gilded Age.

Located on a spacious river harbor along the Lake Michigan shore, Saugatuck and its sister city, Douglas, are an improbable fusion of gracious charm and hip sophistication. In summer, it is packed with eager boaters and beachgoers, but the real magic doesn’t begin until after Labor Day, when the crowds melt away and the area begins to display its softer, more intimate charms.

Locals insist that the waters at Saugatuck’s famous Oval Beach are still swimmable through the end of September (on sunny days, at least, and when the wind is in the right direction). But there’s no getting around the fact that when autumn turns the surrounding hills into a brilliant tapestry of scarlet and gold, attention shifts to the charming shops and restaurants that line the streets of this sweet town.

This is a time for leisurely lunches and dinners, unhurried shopping adventures, wine tastings and twilight strolls along the harbor. And it’s also the very best time to investigate Saugatuck’s reputation for artistic excellence by browsing its fine studios and galleries.

Ever since 1905, when a group of restless students from the Art Institute of Chicago began coming here to paint in the summers, this area has prided itself on being Michigan’s “art coast,” a fact that is celebrated with a series of gallery walks in both towns throughout the fall and winter. The Ox-Bow School of Art, founded in 1910 by those Art Institute students, is still offering classes (now even in winter) and the Saugatuck Center for the Arts features year-round art exhibitions and performances in its 412-seat theatre.

Some of the most popular local summer attractions are still up and running well into fall, most notably the charming Star of Saugatuck II stern-wheeler cruise boat, which is a wonderful way to view the fall foliage. Adventurous visitors can climb the 302 steps to the top of Mt. Baldhead for a sweeping panorama of the colors.

The post-Labor Day calendar in Saugatuck and Douglas is filled with tours, performances and festivals (including a well-attended chili cook-off), but Halloween is probably the area’s favorite fall celebration, with a bewildering number of parties, dinners and parades throughout that weekend.

When it comes to lodging, there are almost no representatives of hotel chains in the Saugatuck-Douglas area, and the few examples that exist are tucked away in unobtrusive spots. Visitors are far more likely to find themselves bedding down in a historic bed and breakfast or boutique hotel near the harbor, or a vintage mom-and-pop motel at the edge of town.

Looking for a different kind of getaway experience? Try one of the recently refurbished vintage motels on the edge of town that provide an upgraded version of classic 1950s lodging. A great example is the Saugatuck Retro Resort (open until the end of October) where partners Rob Goeke and Steve Laughner have turned a rundown motel into a cunningly nostalgic destination, complete with a classic kidneyshaped pool and a convivial community fire pit for cool fall evenings.

The resort is particularly popular with fall cyclists and hikers drawn to the extensive trail system at the nearby Saugatuck Dunes State Park, and with foodies who head east for apple picking and wine tasting. Try the generous array of barrel-aged European style apple ciders at Virtue Cider, which Gregory Hall launched in Chicago’s Roscoe Village and moved to Fennville in 2013.

“The major attraction in fall is probably the restaurant experience here,” says Goeke. “For a town of this size it’s pretty fantastic, and fall visitors find it a lot easier to get a table.”

Fortunately, many restaurants in the area stay open year-round. They range from Lucy’s Little Kitchen in a historic Victorian house—don’t miss the astonishing ahi tuna nachos—to Ida Red’s Cottage by the harbor, famous for hearty and economical breakfasts served on colorful Fiestaware. Saugatuck Brewing company and Everyday People Café are favorites in Douglas, and the sprawling, kitschy Crane’s Pie Pantry now has a winery on the century-old family fruit farm in Fennville.

When winter snows began to blow, visitors tend to snuggle closer to the towns’ central areas, where “retro” is more likely to mean an inviting, 150-year-old boutique hotel like The Maplewood, on Saugatuck’s Village Square.

“Winter is a wonderful time of year here,” says Claressa Lawrence, innkeeper of the 15-room bed and breakfast. “That’s when we see a lot of folks who are looking for a cozy getaway, perhaps some wine tasting and a little shopping, and maybe some skiing or snowshoeing. Mainly, though, we see people who just want to get away and be alone with each other for a bit.”

Fine dining plays an especially a big role in the winter scene in SaugatuckDouglas, and many of the local hostelries host special dinners to celebrate the area’s culinary flair. The Wickwood Inn for instance, is the domain of celebrated food writer Julee Rosso, author of The Silver Palate Cookbook, while The Kirby Hotel in Douglas (once the local hospital) has a well-regarded restaurant, J. Paul’s, under the supervision of chef Mindy Trafman. Holiday décor brings an extra glow to the Bed, Breakfast & Dinner packages at the lovely Belvedere Inn & Restaurant on five landscaped acres in Saugatuck.

And if you need a little more rambunctious fun, you can always hoist a few well-poured drinks with some of the locals at an all-season watering hole like Phil’s Bar & Grille, where everybody in the small community ends up sooner or later when the snow flies.

“This is where we all hang out in the winter, when it gets more relaxed, and we can all catch up with each other,” says hostess Lisa Lungaro. “One of the great things about this town is that there’s really no ‘locals versus visitors’ thing going on. Everybody just accepts everybody else on their own terms.”

This article originally appeared in the 2017 fall/winter issue of Experience Michigan magazine. The contents of this article were checked for accuracy when it was published; however, it’s possible some of the information has changed. We recommend you call first if you have specific questions for the destinations, attractions or restaurants mentioned in this article.

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