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

MICHIGAN

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.

WATER WINGS
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).

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

WELL SPOKEN
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.

The magical outdoor stage at American Players Theatre in Spring Green, Wisconsin. See more photos in the gallery >>

WISCONSIN

Mile after mile of rolling farmland, disinterested dairy cows, fresh air by the lungful. You may have seen southern Wisconsin by car, but it’s a whole different experience from the saddle of a bike—revelatory, even, once you get past the eau de Holstein. Green County—a perfect square of rural Wisconsin that stretches from Browntown on the west to Brodhead on the east and from Belleville south to the Illinois state line—incorporates some 279 miles of paved but near-deserted farm roads, not to mention two former rail lines reborn as crushed-limestone bike trails. In other words: two-wheeler heaven.

Begin your adventure by checking in to Brodhead’s Earth Rider, an eco-friendly, Tour de France–themed boutique hotel and bike shop located one block from the eastern terminus of the 23-mile Sugar River State Trail (we used the hotel as a base to explore the area’s different cycling options). The innkeeper and cycling matriarch Sharon Kaminecki—her daughter specializes in bike-themed art, and her son builds bike frames under the brand name Kaminecki—keeps a binder of suggested road routes; we liked the mildly hilly 25-mile Tour of the Old World, featuring a pit stop at the Amish-run Country Lane Bakery (try the cinnamon rolls).

Or leave paved civilization behind and head straight for the Sugar River trail. Three miles in, you will ride through a picturesque reconstruction of the 19th-century Clarence covered bridge. In another four miles, you will hit the tiny hamlet of Albany, and ten miles on is Monticello, where you can grab a burger at M & M Cafe before detouring to the intersecting Badger State Trail. The short jog is worth it for the chance to pedal through the quarter-mile-long, 120-year-old Stewart Tunnel, a former railroad passage that is dank, dripping, and utterly thrilling: Because the tunnel curves, you will find yourself in total darkness at its center (check your bike-light batteries before going in). Kids love it.

Hop back on to the Sugar River trail, and you are just six miles from New Glarus—Wisconsin’s “Little Switzerland”—at the path’s western end. Fat Cat Coffee Works sits feet from the trail and serves a mean chicken salad, while the traditional Swiss standby Glarner Stube offers cheese every which way (rösti, fondue, beer-cheese soup). For fuel of a different kind, stop by the top-notch New Glarus Brewing Company; the award-winning beer is also available at local watering holes including the cozy Puempel’s Olde Tavern. Go ahead: You’ve earned it.

MILWAUKEE
The new Iron Horse Hotel caters to upscale motorcycle enthusiasts (and others)—and the recently opened Harley-Davidson Museum is nearby.

HORICON MARSH
For a close look at the marsh’s 200-plus bird species, swing by the Marsh Haven Nature Center, which offers three different trails—wetland, prairie, and woodland—and an observation tower.

AMERICAN PLAYERS THEATRE
The walk from the parking lot can take 30 minutes; show up even earlier and enjoy a pre-play picnic—take your own or order one beforehand (serves six to eight people; $87.50).

CUT-RATE CAMPING Situated about 145 miles northwest of Chicago, Wisconsin’s Dodge County operates five lovely little parks that provide low-cost campsites ($14 a night; $18 with an electrical hookup) with showers and other amenities nearby and within easy access of Horicon Marsh, Beaver Dam Lake, and the 34-mile-long Wild Goose State Trail. Call 920-386-3700 or go to co.dodge.wi.us/landresources/recreation.

There are few more fanciful tales in the Shakespeare canon than The Winter’s Tale, and few more delightful settings for that peculiar romance than the outdoor stage of American Players Theatre, which this year celebrates its 30th-anniversary season in the rolling hills surrounding Spring Green, Wisconsin. Those same hills nurtured the young Frank Lloyd Wright, and later served as the setting for his stylish—and, at times, cursed—rural retreat, Taliesin. Today, the architect’s home is open to the public—after a seasonal break, tours resume in April—and can be paired with the theatre for a weekend of Dairyland culture. This season, in addition to performing Shakespeare’s Winter’s Tale and The Comedy of Errors, as well as plays by Shaw, Noël Coward, Harold Pinter, and Eugene O’Neill, American Players introduces its new indoor 200-seat Touchstone Theatre. But the beguiling open-air stage remains the draw—and when the forlorn king in The Winter’s Tale, looking to describe his lost wife’s eyes, doubly invokes the stars, playgoers need look no farther than the night sky above for confirmation of the sovereign’s heart-rending metaphor.

In LaSalle, the Volunteer lets people travel in a replica of a 19th-century, mule-driven canal boat. See more photos in the gallery >>

ILLINOIS

When is a canoe like a time machine? When it’s used on a journey that spans five centuries. That’s the case as travelers track the route of the old Illinois and Michigan Canal, the 161-year-old inland waterway that was the brainchild of a 17th-century explorer—and that even today, whether traveled by auto, bicycle, boat, or on foot, still transports visitors to another realm: the past.

Begin your trip in the western suburbs at the Chicago Portage National Historical Site. A monumental Cor-Ten steel sculpture by Ferdinand Rebechini depicts Louis Jolliet, Père Jacques Marquette, and a Native American guide, who arrived at the portage in 1673. The visit prompted Jolliet to promote building a canal uniting the Great Lakes and the Mississippi River; his dream was realized in 1848 with the opening of the I&M Canal, an event that facilitated Chicago’s rise as a great Midwestern metropolis.

For motorists, the 75-mile-long Canal Corridor Driving Tour begins in Lemont and extends to LaSalle on the Illinois River; look for the blue and yellow road signs depicting a boy and a mule. Don’t miss the city of Lockport, which originated in 1837 as the canal’s headquarters. Check out the handsomely restored Gaylord Building, a onetime canal depot now used as a visitors’ center—its Public Landing Restaurant makes a good lunch stop—and the I&M Canal Museum, inside the former office and home of the canal superintendent.

Cyclists and hikers will prefer the 61-mile-long I&M Canal State Trail, which follows the canal’s old towpath, along which mules pulled the canal boats. The trail begins in Channahon State Park; canoeists can explore the 15 miles of open water between Channahon and Gebhard Woods State Park. For a glimpse of Illinois as it looked when Jolliet and Marquette first visited, make the short detour to the 2,537-acre Goose Lake Prairie State Park, which contains the largest prairie remnant in the state. Farther on, near Ottawa—where statues mark the first Lincoln-Douglas debate—Buffalo Rock State Park is home to Michael Helzer’s gigantic Effigy Tumuli, which evoke the region’s Native American mound builders.

The town of Utica is the gateway to Starved Rock State Park, which, with its lodge, cabins, and campgrounds, makes a good overnight stop; it also offers some insights into the final days of the state’s eponymous early inhabitants, the Illini. The next day, push on to LaSalle, whose Lock 14 is the only lock on the canal whose wooden gates have been restored. Don’t leave town without visiting the Hegeler Carus Mansion, a Second Empire mansion designed by William Boyington, the architect of Chicago’s Water Tower. Cap off your visit with a ride on the Volunteer, a replica of a 19th-century canal boat, powered (for part of the trip) by two mules named Larry and Mo.

LINCOLN’S LOVE
While commemorating Abraham Lincoln’s 200th birthday, let’s not forget his putative early love, Ann Rutledge. After she died in 1835, Rutledge was laid to rest in Old Concord Cemetery (a modern-day gravestone marks the site). Fifty-five years later, her remains—three pearl buttons, a buckle, and some wisps of hair—were dug up and buried again in Petersburg’s Oakland Cemetery, not far from the rebuilt frontier village of New Salem, where the couple may have courted.

THEY PLAY IN PEORIA The Cubs star Ryne Sandberg may have moved on, but baseball’s Midwest League Peoria Chiefs, the Class-A affiliate of the Chicago Cubs, still play at O’Brien Field (730 S.W. Jefferson Street; 309-680-4000). After Sandberg, the Chiefs’ manager for the last two seasons, won a promotion to the Tennessee Smokies (the Cubs’ Double-A team), Marty Pevey took over as manager. The team’s 2009 home season kicks off on April 9th when the Kane County Cougars travel to Peoria for a three-game series.

Auto races at the Indianapolis Motor Speedway, which this year celebrates its 100th anniversary—with a balloon race. See more photos in the gallery >>

INDIANA

As they drive south on I-65 for a two-day trip through central Indiana, travelers will learn two things: Despite Chicago’s well-deserved reputation as the country’s architecture capital, it does not hold a patent on beautiful buildings. And watch out when you visit the Indianapolis Motor Speedway—there’s a good chance a golf game might break out.

Before ogling the architecture of Columbus, let’s start with Indianapolis and its famous speedway, which this year celebrates its 100th anniversary. The Indianapolis 500, the track’s premier race, takes place on May 24th, but centennial events kick off the weekend of May 1st with a balloon race (the first race at the track, on June 5, 1909, was a balloon race) and a half-marathon for runners. Practice runs for the Indianapolis 500 begin the following week, and there are other auto-racing events throughout the summer—among them, the Allstate 400 on July 26th (tickets for all speedway events are available online).

Even on non-race days, the track is worth a visit. In addition to a short movie packed with exciting Indy 500 highlights, the track’s Hall of Fame Museum regularly displays 75 cars from its automobile collection, including Ray Harroun’s Marmon Wasp, which won the first Indy 500 in 1911. (Harroun’s winning time was six hours and 42 minutes; the winner in 2008 completed the race in three hours and 29 minutes). The Pete Dye–designed Brickyard Crossing Golf Course offers a duffer’s perspective of the track, with four of its 18 holes situated within the racing oval.

Auto racing and golf aren’t the only sports Indianapolis offers. Check into the Conrad Indianapolis, the city’s most luxurious hotel, and professional basketball, baseball, and football are all within walking distance. As spring gives way to summer, a changing of the guard takes place at Conseco Fieldhouse, where the NBA’s Pacers make way for the WNBA’s Fever (the Pacers host the Bulls on March 31st; the Fever home season gets under way on June 7th). The Triple-A Indianapolis Indians, a minor-league baseball team affiliated with the Pittsburgh Pirates, plays the first of its 72 home games at Victory Field on April 9th. And, yes, Peyton Manning does have another career besides making TV commercials: his Indianapolis Colts commence their 2009 NFL season at the year-old Lucas Oil Stadium in August. Cap off any of these sporting events with dinner at Mo’s A Place for Steaks and you might catch sight of at least one species of pro ballplayer.

But Indianapolis is more than just a great escape for sports enthusiasts. With its promenade, zoo, IMAX Theater, and museums (including the Eiteljorg Museum of American Indians and Western Art), the city’s White River State Park is a delightful alternative for folks who would rather not follow the bouncing ball—or the speeding racecar.

WHITE RIVER STATE PARK
The White River State Park Pass ($42 for adults, $30 for children) provides 25 percent savings on one-time admission to six prime attractions, including the newly reopened NCAA Hall of Champions.

THE OTHER NASHVILLE Just west of Columbus, Brown County is home to Indiana’s largest state park (with fishing, camping, and miles of hiking, biking, and bridle trails); two wineries and a pair of covered bridges; and a thriving art scene, centered in the town of Nashville, that dates back to the early 20th century. The 43rd annual Bill Monroe Memorial Bean Blossom Bluegrass Festival is June 13th to 20th.

Since 1942, when the Finnish architect Eliel Saarinen put up his First Christian Church in this small town on the prairie, the city of Columbus has assembled a remarkable collection of more than 70 modern buildings and pieces of public art. Its roster of top-tier architects and artists includes I. M. Pei, Henry Moore, Eero Saarinen, and Chicago’s Harry Weese, who has crafted nine buildings for the town. His L. C. Schmitt Elementary School, built in 1957, was the first structure whose design fees were paid for by a foundation sponsored by Cummins Inc., part of the public-private partnership that nurtured the city’s big-name building boom.

Start your visit with the two-hour bus tour that departs most mornings from the visitors’ center. Spend your afternoon exploring some of the buildings at a more leisurely pace; the churches alone—especially First Christian, First Baptist, and North Christian—warrant a close look inside and out. Don’t miss the city’s 19th-century buildings, including the Bartholomew County Courthouse and the 145-year-old Joseph Irwin home. After dinner at Smith’s Row, take one last walk around town: Some Columbus buildings, such as the Pei-designed library, look their loveliest when illuminated from within at night.