Distance: 90 miles
Driving Time: 1.5 hours
Chicago might be your kind of town, but its proximity to other Midwest treasures also makes it the ideal jumping-off point for getting out of the city. Our choice?Harbor Country, Michigan, a cluster of eight lakefront communities situated along the charming, two-lane Red Arrow Highway and connected by windy, tree-lined back roads. The weekend getaway of choice for Chicago's well-heeled crowd (hello, Oprah), Harbor Country nonetheless retains a casual, beachy feel.
Major construction has made a mess of the city's main road, the Dan Ryan Expressway, aka I-90/94 East. The Illinois Department of Transportation begs us all to (caps theirs) AVOID THE DAN RYAN (www.avoidtheryan.com). It can be difficult to skip the expressway entirely, depending on where you're coming from, but try getting on South Lake Shore Drive instead. Turn right onto East 57th Street and follow it to South Cornell Avenue. Bear right onto Midway Plaisance, then turn right onto South Stony Island Avenue; follow signs to I-94, and you're home free. Leave the thoroughfare behind at Chesterton, Indiana (exit 26), for leafy Route 12, aka the Red Arrow Highway. The open road follows Lake Michigan to—and through—the eight towns, from main locale New Buffalo to quiet bookend Sawyer, where newly-opened upscale establishments have brought a touch of the big city to the small town. For an even prettier drive, follow signs from Route 12 to the Michiana Shoreline, where you'll drive alongside Duneland Beach and through wooded, quaint (read: expensive) neighborhoods.
Related: Things to Do in Southern Michigan
Hike the Warren Dunes State Park trails (12032 Red Arrow Hwy.; Sawyer, MI; 269/426-4013) or scale Mount Baldy (Highway 12 and Beverly Dr.; Michigan City, IN), the Indiana Dunes National Lakeshore's largest "living" dune (translation: its sands are constantly shifting and moving southward). At its peak, the dune looks out over Lake Michigan and provides a view of Chicago's skyline from afar. It's the ideal location for a picnic; we recommend stopping at the Goddess and Grocer (25 E. Delaware Pl., Chicago; 312/896-2600; www.goddessandgrocer.com) on your way out of Chicago. At this gourmet food shop, you can make your own salad, order a ton of sides (try the grilled asparagus with truffle oil), or stock up on overflowing sandwiches, such as the Smokin' Brisket with caramelized onions or the Italian Slam with prosciutto, mortadella, and provolone.
Take a Wine Break
If all the fresh air has gone to your head, check out one of southwest Michigan's wineries (miwinetrail.com), such as Tabor Hill (10243 Red Arrow Hwy.; Bridgman, MI; 269/465-6566), where the claim to fame is the super-sweet cherry wine. Tabor claims that it's "the closest thing to cherry pie in a bottle." True, it's not the most sophisticated-sounding selection, but it is an undeniably fun way to expand your wine-tasting experiences.
Snap up Art and Antiques
With its countless collectible shops and roadside marts, Red Arrow Highway might as well be called Antique Alley. From the fur-trimmed three-quarter-length coats —cheaper and cooler than H&M knockoffs—at Dunes Antique Center (12825 Red Arrow Hwy.; Sawyer, MI; 269/426-4043; www.dunesantiques.com) to the remarkably comfortable Ivory Coast mahogany carved chair at Stewart James Antiques & Galleria (12619 Red Arrow Hwy.; Sawyer, MI; 269/426-3133), over the past decade, the once-sleepy Arrow has become an antique hunter's dreamMay we suggest that after you spend a few hours sifting, you refrain from buying those German beer-garden chairs and head to Three Oaks, Harbor Country's up-and-comer, where modern-art galleries exhibit local works. In addition, Vickers Theatre (6 N. Elm St.; Three Oaks, MI; 269/756-3522; www.vickerstheatre.com), a restored turn-of-the-last-century film house, and Acorn Theater (107 Generations Dr.; Three Oaks, MI; 269/756-3879; www.acorntheater.com), a performing arts space that hosts Chicago blues acts, have made a name for this once off-the-grid town. And don't miss two stores: Springdale (19 S. Elm St.; Three Oaks, MI; 269/756-9896; www.springdalefurnishings.com), housed in an old bowling alley and specializing in restored Heywood-Wakefield furniture, and Ipso Facto (1 West Ash St.; Three Oaks, MI; 269/756-3404), local Brandon Nelson's quirky collection of art and antiques, where you can splurge on the coolest present ever—a working Lego phone.
Where to Eat
Harbor Country does not want for eateries, but our favorite is Blue Plate Café (15288 Red Arrow Hwy.; Union Pier, MI; 269/469-2370), a breakfast-and-lunch-only space set in a cozy little shack, where sunlight pours over the colorful china lining the yellow walls. The restaurant uses local ingredients from independent farmers. Temptations include the Henhouse Hash, a roasted Amish chicken sautéed with herbs, onions, and potatoes, and the Gringo Griddle—pan-roasted black beans, sweet corn, and onions, topped with homemade salsa and a dollop of sour cream. Carolina's On My Mind, the staple lunch sandwich, is also hard to pass up: Who knew turkey, barbecue sauce, pickles, and coleslaw were made for each other?For the drive back, take a few homemade cookies—in particular the spicy Joan's Giant Gingers and the buttery Chock-Full-O-Chips.
Choose a B&B, a B&B, or a B&B. If you've brought the kids along, book a night at the Lakeside Inn (15251 Lakeshore Rd.; Lakeside, MI; 269/469-0600; www.lakesideinns.com), a 31-room hotel built in the 1880's and restored in the 1990's as part of the area's renaissance. With its rustic, creaky charm, the place brings to mind summer camp. Chill out with a book in front of the lobby's stone fireplace or in a rocking chair on the 100-foot-long front porch. (Be forewarned: During the winter off-season, its empty hallways can recall Psycho.) If you've left the little ones behind, check into the elegant Sandpiper Inn (16136 Lakeview Ave.; Union Pier, MI; 269/469-1146; www.sandpiperinn.net), owned by husband-and-wife team Veronica Lynch and Jim Reilly, who traded in their Chicago corporate lives for the attractions of Harbor Country. Watch the sun rise over Sandpiper's private beach from your veranda (every room has one), borrow a bike, induce sweet dreams with milk and homemade chocolate-chunk cookies, and wake up to Veronica's feather-light pancakes.
To live like the locals, dress down and eat cheap. The Whistle Stop deli (15700 Red Arrow Hwy.; Union Pier, MI; 269/469-6700), which has a log-cabin exterior, offers enlightened deli foods such as grapeseed oil, breads from local baker Bit of Swiss, and a mean Choo Choo Charley tuna melt. Local hangout Stray Dog Bar & Grill (245 N. Whittaker; New Buffalo, MI; 269/469-2727) isn't fancy, but who can resist burgers, jerk chicken, chili, ribs, live music, and lots of beer?