Ann Arbor
A roughly 50-min. drive west of downtown Detroit on I-94, Ann Arbor is filled with terrific restaurants, bars and shops — and the University of Michigan, of course, which dominates life here. The sprawling, grassy campus, with its mix of Gothic and modern architecture, is worth strolling; on the weekend of a home game, the campus and surrounding town fairly vibrate with collegiate cheer. Aside from Michigan Stadium ("The Big House") — the largest stadium in college athletics, with 107,501 seats — other worthwhile destinations include Matthaei Botanical Gardens and Nichols Arboretum. (Ann Arbor is "Tree City," after all.) Also, while you're in town, be sure to stop by Zingerman's Roadhouse for some high-quality American fare; if you're a carnivore, order the beef brisket.
Windsor, Ontario
Canada's automotive capital is gritty, but several relatively recent building projects, including casinos (concerts at the Caesars Windsor Hotel & Casino regularly feature the likes of John Mellencamp, Tony Bennett and Al Green) are helping gloss the city's image. O.K., so there are more than a few Tim Horton's here, but Windsor is also teeming with excellent Vietnamese and Pakistani restaurants. And it has the best views of Motown, right across the Detroit River; take a stroll along the walkway by the river downtown.
There are two main ways to get to Windsor from Detroit: the Ambassador Bridge, which is just to the south of downtown, or the Detroit-Windsor Tunnel, which emerges right next-door to the GM Renaissance Center, a gleaming shopping, hotel and office complex — and headquarters of GM — on the waterfront downtown. If you take the tunnel, expect up to 30-min. delays during rush hours. Oh, and be sure to have the required government-issued identification cards to get back across the border.
Birmingham
For relief from Detroit's grit, drive 30 min. north to Birmingham, a city of nearly 19,000, which locals consider Michigan's answer to Beverly Hills. That's quite a stretch. But Birmingham remains the center of Michigan's suburban wealth. Check out the shops, restaurants and bars along East Maple Road or Old Woodward Avenue (you'll find the usual outposts of chains like Panera Bread and Starbucks). For a more regal dining experience try The Townsend Hotel's The Rugby Grille, where brunch serves up a Crème Brulee brioche French toast.