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Following the Lake Michigan Shore Wine Trail
Around an hour's drive from Chicago (close to four hours from Detroit), the Lake Michigan Shore Wine Trail is located at the southwest border of Michigan, near the resort towns of New Buffalo, St. Joseph, and Saugatuk. The countryside in the area contains over 10,000 acres of grapes and twelve wineries. It's easy to plan a weekend getaway (or even a day-trip from Chicago) to this beautiful wine region near the Lake.
Where to Drink
With a dozen wineries to chose from, it can hard to narrow down your choices. But you'll need to limit yourself to four or five per day (those little tastes do add up!). Warner Vineyards, St. Julian, and Contessa Wine Cellars all offer free tastings. Free Run Cellars and the Round Barn Winery are owned by the same family. Buy a $5 souvenir wine glass at one, and it will cover your tasting fees at the other as well. At Round Barn, you can taste five wines, one dessert wine, and one of their made-onsite vodkas. There is also a beer-tasting room where you can sample some of the beers they brew. Tours of the wine cellar, cave, brewery and distillery are available for groups of 20 people at $10 each, and you can enjoy lunch at the picnic facilities that overlook the vineyards.
Where to Stay
You'll find some hotel chains in the area, but for a little more character, check out the Oliver Inn Bed and Breakfast, a restored Victorian inn where rooms start at $100 per night. The Marina Grand in New Buffalo is a little swankier. Rooms run $140 to $200 per night, but feature luxury bedding, marina views, and the hotel has a fitness center and indoor and outdoor pools.
Where to Eat
New Buffalo and St. Joseph have the most options for dining. Here you'll find everything from casual pub food at the Stray Dog Bar and Grill to fine dining at The Dining Room at Clearbrook. For a special occasion, try Tabor Hill, which serves meals made from local ingredients in a romantic setting. If you didn't buy enough wine on your tasting tour, New Buffalo's Vino 100 wine shop is the perfect place to stop. They have over 100 bottles that cost under $10.
What to Do
Other than staining your lips purple at the area's wineries, you can take advantage of the Trail's lakeside location with swimming, sailing, or relaxing on the beach near Saugatuk. You'll also find several u-pick fruit farms, a cider mill, and your standard assortment of resort town stores - candy shops, ice cream parlors, and "resort wear" boutiques.
If you don't have a designated driver and wish to have more than a few samples, there are several companies that offer transportation along the route. Fruitful Vine charges $50 per hour for transportation in a Suburban (which seats five) or offers four-hour hop-on bus tours for $39 per person in summer.