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Weekend Getaways

Whatever your passion—architecture or antiques, pro sports or history, outdoor adventures or romantic wineries—the Midwest offers nearby destinations to satisfy even budget-conscious travelers.

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Dark clouds overshadow the vineyards at Tabor Hill Winery & Restaurant near Buchanan, Michigan. See more photos in the gallery >>


The Midwest offers nearby destinations to satisfy every passion, be it architecture or antiques, pro sports or history, outdoor adventures or romantic wineries. Here are suggestions for lively and economical trips in Illinois, Indiana, Wisconsin, and Michigan—with a couple of high-end splurges (think new luxury hotels) tossed in for those special occasions. For addresses, see our Resources.

KEY: Approximate distance and driving time from Chicago


Blazing a trail across southwestern Michigan, the Red Arrow Highway—which honors the U.S. Army’s acclaimed 32nd Division—links the small towns and golden beaches of Harbor Country. But the thoroughfare is also a gathering spot for the area’s antique shops, and it points the way toward a bunch of wineries that offer tours, tastings, and an opportunity for a splendid dinner.

Start your trip in Lakeside. Check into the Lakeside Inn, an evocative old hotel with a 100-foot-long porch, stone fireplaces, a ballroom, and a private beach. Good antiquing lies in nearly every direction, beginning with two shops right in town: Charm Cottage, with a courtyard filled with planters, outdoor furniture, and salvaged architectural treasures, and Lakeside Antiques, which collects European and American antiques inside several buildings. Five miles to the south, in Union Pier, nose around The Plum Tree for restored floor lamps, tables, and other antique household items. About three miles north, in Harbert, the Harbert Antique Mall conveniently gathers 50 dealers from Michigan, Illinois, and Indiana under one roof. Nearby, Marco Polo elegantly blends Midwestern finds with items gathered from abroad. If you are looking for something new, Vincent Tables proffers handcrafted, one-of-a-kind pieces of furniture.

Away from the shore, in the charming town of Three Oaks, you will find the quirky Ipso Facto—the eclectic offerings include paintings, furniture, architectural ornaments, and Americana—and Springdale, which specializes in mid-20th-century Heywood-Wakefield furniture. Direct your car northward for one final stop: Shawnee Road Antiques. Gathered inside three big buildings southeast of Baroda are hundreds of pieces of furniture, as well as a vintage clothing store—Apparel from the Past—that showcases women’s fashions from the 1930s and ’40s.

From Shawnee Road, it’s a ten-minute drive to the Round Barn Winery, which, in addition to more than a score of wines—try the dry white Vineyard Tears—also produces fruit brandies, vodka, and a handful of beers. (Don’t wait until fall to register for the popular October winemaking classes.) About ten miles south, Berrien Springs is home to two good wineries: Lemon Creek, which, with its rich array of fresh fruit and distinguished cabernets, is as much Midwestern farm as European vineyard, and Domaine Berrien Cellars, which 17 years ago began replacing its cherry orchards with vinifera (that is, Old World) grapevines. Sample one of the award-winning reds and judge for yourself the success of this experiment. Finally, end your day near Buchanan at the Tabor Hill Winery & Restaurant. After touring the vineyard, reflect on the day’s discoveries over a fine meal (reservations are a must) and, of course, a glass of wine.

With more than two miles of shoreline and sand dunes that rise some 240 feet above Lake Michigan, the 1,952-acre Warren Dunes State Park offers swimming and other summertime water sports. But the park also has wildflowers and a hardwood forest, six miles of hiking trails, 180 campsites—and its Tower Hill has for decades been a favorite launching spot for hang gliders (you will need to get a permit at the park).

Carl Sandburg once penned an ode to the bologna at Drier’s Meat Market, whose charcuteries provide the perfect foundation for a Michigan picnic.


The Three Oaks Spokes Bicycle Club, which sponsors the popular Apple Cider Century (held this year on September 27th), has prepared 14 self-guided cycling tours that explore the backroads of Michigan’s Harbor Country. Download maps of the routes, which range from 5 to 60 miles, at applecidercentury.com—or drop by the Dewey Cannon Trading Company in Three Oaks, where you can also rent bikes.



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