The Wine Maker's Harvest Dinner hasn't even started before visitor Jim Winkelman of Bloomfield, Michigan, anticipates what's to come. "Michigan has very food-friendly wine," Jim says. "They have a higher acidity level and less alcohol, so wine pairing is much easier than with California wines."
Spoken in true Great Lakes State style. Still, after more than a decade attending these five-course dinners, Jim has learned a bit about what makes a good match. A spicy Edelzwicker brings out the subtle hint of roasted poblano in the soup. A tannic Cabernet Franc tones down duck's gaminess. The dry Riesling gets mixed reviews. Does it complement the sweet cider sauce or fight it?
It's the kind of conversation winemaker Doug Welsch likes to hear. "The world of wine is terrifying to the neophyte," Doug says. "With tens of thousands of wines to choose from at every price point imaginable, wine drinkers are afraid they will pick the wrong wine and look like an idiot to their friends."
These Harvest Winemaker's Dinners ($70 per person, in November, call for dates) curb that intimidation for novices -- and help aficionados make the most of a table full of flavors. (800) 432-6265; fennvalley.com  -- Amy S. Eckert
This Brady Street neighborhood wine bar proves that Brewtown has definitely gotten on the grape train. Amid charmingly mismatched chairs, cherubs and taxidermy, manager Pete Bressert (pictured) helps patrons with their wine selections. A sparkling Gruet Blanc de Noir complements a creamy Gruyère cheese plate. A spicy Pinot Noir pairs perfectly with garlicky crimini, shiitake and portobellos. And Pineau des Charentes, a dense dessert wine, underscores the peach Foster, served with vanilla ice cream and bourbon caramel sauce.
It's no surprise that Jaclyn Stuart, former sommelier at Kohler's elegant Immigrant Room and coauthor (with Jeanette Hurt) of The Complete Idiot's Guide to Wine and Food Pairing, held the book's launch party at Balzac. Here, the prices are reasonable, and the atmosphere is inviting -- even for someone looking to shed her fears. (414) 755-0099; balzacwinebar.com  -- Manya Kaczkowski
One of Chicago's most popular wine bars, Bin 36 has a motto: "The best way to learn about wine is to drink it. Throw away the vintage chart and invest in a corkscrew."
The selection here is outstanding and reasonably priced ($5-$15.75 a glass). Tips on the menu explain differences between varietals and the regions where the grapes are grown, and servers will help pair wine. (All entrees have a wine bin number for suggested pairings, too.) Patrons settle into booths in this clubby--if a little noisy--River North spot near Marina City, read the handy flight guide, chat with their servers, then let their taste buds lead the way. (312) 755-9463; bin36.com  -- Kit Bernardi
Pictured: Colorfully plated whitefish delights at Bin 36.
It's happened to everyone: Eager to try something new, you splurge on an unfamiliar wine--and hate it. Tastings, a wine bar in the luxurious Conrad Hotel, tries to ensure you'll never have that problem.
Classy-looking wine vending towers invite visitors to use prepaid debit cards to dispense tasting portions of more than 100 wines ($40 is more than enough for two people), and the selection changes often. That means you can try a mysterious Merlot, compare Rieslings from different regions or simply refine your wine palate, all for just a few dollars a taste.
The samples are generous, and it's fun to wander among the machines before settling down to a dinner of Mediterranean-influenced small plates with a glass of your favorite new Pacific Rim sweet Riesling. (317) 423-2400; awineexperience.com  -- Ashley Petry
The concept of terroir comes to life as you follow the Mississippi River to 10 wineries in Wisconsin, Minnesota and Iowa. At each tasting room along the two-year-old trail, vintners explain how the rolling hills, steep bluffs and pleasantly cooler temperatures affect a wine's flavor.
Hybrid grapes such as Foch, Frontenac, La Crescent and Marquette flourish here, and tasting reveals how they make the region's wine distinctive. Events throughout the year pair local foods and wines, and an upcoming holiday celebration puts a festive spin on the perfect pairings. (507) 474-9463; greatriverroadwinetrail.org  -- Melanie Radzicki McManus
Pictured: Minnesota's Cannon River Winery, along the Great River Road Wine Trail, holds pairing events throughout the year.
A favorite among Door County's 10 wineries, Simon Creek courts both grape-only purists and those who favor sweeter fruit wines. The scenic country location, temperate Lake Michigan climate and impressive range of flavors (the winery grows about 20 grape varieties) make an irresistible combination.
Most visitors start with a free winery tour, followed by samples. Whether you prefer the semisweet Untouchable Red, named for Al Capone's attempt to buy Simon Creek farm for his bootleg empire, or American Viognier, for its hints of lime and grapefruit, you're likely to find something that satisfies.
Buy a bottle of your favorite ($15-$18), then sit back and relax on the winery's sprawling patio. You can order cheese and crackers or even bring your own snacks and hold your own leisurely pairing session. The mood is especially delightful on Sunday afternoons, when live music entertains, and the weekend seems to stretch out a little longer as you sip a glass or two in the waning light. (920) 746-9307; simoncreekvineyard.com  -- Lisa Meyers McClintick
While Top Chef Master Tony Mantuano is one creative force behind this destination Italian restaurant along the Magnificent Mile, a different narrator escorts diners through the restaurant's Aceto Balsamico tasting menu: the grape.
Masterful wine pairings and a balsamic vinegar progression take patrons on a tour through Italy's vineyards and into the barrels of vinegar of craftsmen who start with nothing but grape must, i.e. juice. "People are passionate about wine more than ever," says Tony, who attributes Americans' love affair with the grape to an increase in international travel. "They want to know more."
The $160 seven-course journey (plus $90 for wine pairings) is such an immersive culinary education that it's no wonder Chicago's only four-star Italian restaurant has earned kudos from The James Beard Foundation. The steep price buys an epicurean adventure that novices and oenophiles alike will savor.
Each course demonstrates how the balsamic vinegar changes as it ages, from its early, light and sweet days to the pungent, lingering incarnation that comes from more than 25 years spent aging in a wooden barrel. Along the way, the flavor and texture of the balsamic flirts with braised pork-filled ravioli, creamy Acquerello risotto, wood-roasted honey lacquered duck breast and Italian-style doughnuts with balsamic zabaglione.
Throughout the meal, a sommelier selects wines that make flavors flourish. "Just like bread or salt or olive oil, wine is another seasoning that can add or take away from a dish," says former sommelier Steve Alexander. "We look for synergy." Somewhere between the pressed grape's balsamic and the fermented grape's wine, that's just what Spiaggia found. (312) 280-2750; spiaggiarestaurant.com  -- Kate Silver
Pictured: Braised pork-filled ravioli is among the offerings at Spiaggia.
Old-school funk music pumps through a tent at The American Club resort, and Chicago celebrity chef Graham Elliott Bowles trots between rows of tables, fists clenched in the air, shouting hello to the more than 200 people gathered to watch him make his spin on Christmas classics.
The session, one of dozens that take place during Kohler's Food and Wine Experience, brings some of the biggest-name chefs to this AAA five-diamond resort 55 miles north of Milwaukee (October 20-23, 2011).
Foodies who dine at buzzworthy restaurants, home cooks who can't wait to try new recipes and wine enthusiasts all find their way here; the 7,000 attendees range from students in their 20s to seasoned cooks in their 70s. One-hour sessions run $25 to $40 each (special dinners can cost much more). At all of them, the audience gets generous wine pours and learns from the winemakers why a particular vintage works with the amazing dishes coming out of the oven and with the award-winning Wisconsin cheeses being served.
Most of the license plates in the parking lot are from Wisconsin, and visitors told us they hoped word about their 11-year-old "secret" festival wouldn't get out--but it's just too good not to share. (800) 344-2838; destinationkohler.com  -- Kendra L. Williams
Pictured: Food Network celebrity chef Anne Burrell cooks for crowds at Kohler's Food and Wine Experience.
The $110 nine-course tasting menu (plus $55 for wine pairings) isn't really dinner. It's an event.
Settle in over the delicate tang of coffee-scented fluke tartare enhanced by a brightly fizzing flute of champagne; roughly three hours later, you'll find yourself at the deeply satisfying finale of goat's milk caramel ice cream and Criollo chocolate paired with a selection of tawny ports.
The intricacy and scope of such elaborate fare certainly have the potential to be intimidating. Is it a faux pas to sip Chardonnay with foie gras? Is Pinot Noir acceptable with Peking duck? And if you have to ask, will you look foolish?
Of course not, says Blackbird sommelier Chris Nostvick. Servers can explain precisely how a late-harvest French Chardonnay brings out the flavors in garlic-braised snails or why the pickled cherries with slow-cooked halibut are enhanced by an aromatic Sancerre.
"I love talking to people about wine, but it's a conversation, not a lecture," Chris says. "There are no stupid questions. There are no hard and fast rules. I see wine as consumable art, and I encourage people to explore it."
That friendly vibe is crucial, says Chef de Cuisine David Posey, the creative culinary force behind dishes like zucchini gazpacho with cuttlefish and squash churro (paired with an Alsace Riesling). "We really want to keep the food and wine extraordinary and the atmosphere relaxed and comfortable," David says, "like you're going over to a friend's house."
Sure. If you have a friend who cooks like no other and has one stellar wine list. (312) 715-0708; blackbirdrestaurant.com  -- Catey Sullivan
(A version of this story appeared in Midwest Living® September/October 2011.)