In tiny Nappanee, an Amish man parks his buggy by a gas pump, a living metaphor for the way new and old coexist in northern Indiana. Some people come here for classic Amish Country: 29 kinds of pie at Das Dutchman Essenhaus, hand-sewn gifts and homemade jellies at Little Helpers Quilt Shop, treasure-hunting at the Shipshewana Flea Market. But towns like Goshen, Middlebury and Elkhart also are modern communities.
For theater-lovers, summertime means outdoor Shakespeare. But in downstate Illinois, that takes on a fresh new form. Want improv Shakespeare? Sing-along Shakespeare? Or just a performance of his classics (including A Comedy of Errors this year)? Starting in May, and running through mid-August, the Illinois Shakespeare Festival in Bloomington-Normal reveals its ode to the Bard. Other draws to the area: Bloomington’s restored 1800s buildings house farm-to-table restaurants, shops and live-music venues. Inside the three-story courthouse, a museum highlights the area’s historical treasures.
This town embraces the quirky and classy in its arts, museums, shops, dining venues and outdoor activities. Even its farmers market is a Bohemian rhapsody of local produce, entertainment, art and political activism on the state capitol square. Wander the paths and trails at Olbrich Botanical Gardens or the University of Wisconsin Arboretum; admire the art at Chazen Museum of Art or the Madison Museum of Contemporary Art; take a leisurely cruise around Lake Mendota or Menona; and be sure to work up an appetite—Madison's 600-plus restaurants offer something for every taste.
Illinois’ third-largest city spent years watching travelers whiz by on Interstate-90 on their way east to Chicago. Now, thanks to a revitalized downtown, an emerging foodie scene, new cultural attractions and beautiful public gardens, word is getting out: You’d be crazy not to stop. The tranquil Anderson Japanese Gardens (pictured) is just one of the draws to the area.
Shops and restaurants in century-old buildings have long attracted visitors to this town of 3,500. But take time to hike, cruise the river or ski the slopes, sip local wines, taste beer and ... do some shopping.
Art, music and food festivals fill the calendar, and the compact downtown has just as diverse offerings. Watch the Milwaukee Art Museum's striking Quadracci Pavilion open and close its "wings"; catch the Milwaukee Brewers in Miller Park; tour the Pabst Mansion; or take a simulated motorcycle ride at the Harley-Davidson Museum.
This stretch of Lake Michigan coastline offers wide sandy beaches, towering dunes, great birding, easy bike trails and interesting history. Head to neighboring Chesterton for creative burgers at the Octave Grill and a pleasant night at Dunes Walk Inn, a restored 1881 mansion.
An hour west of Chicago’s Loop, the Fox River provides a soothing backdrop to towns brimming with indulgent eats, stores housed in historical homes and posh places to stay. Three towns along the winding river offer restful diversions with a nod to history: Catch a household name playing at St. Charles’ historical Arcada Theater, or just 3 miles south, explore Geneva’s shopping district, where boutiques fill preserved storefronts. And just minutes from Oswego’s charming Main Street—with brick-paved sidewalks—is a family-run winery.
A spring-fed lake and the new Three Oaks Recreation Area—with beach, boardwalk, playground, spray park and hiking trails—await visitors. Indoors, try the eclectic shopping and standout dining. You can take the Metra train to Crystal Lake from downtown Chicago, but to enjoy both the beach and the downtown shops and restaurants, it's best to drive.
New Buffalo (pictured), St. Joseph and Benton Harbor provide pristine beaches, great shopping, lakeside restaurants and front-row view of sunsets over Lake Michigan. Imagine biting into crabcakes with mango salsa at Schu's Bar and Grill or digging your toes in the sand while you listen to an evening concert at Weko Beach.
Great outdoors, grown-up eats and classic clubs make for two cultured cities—especially appealing in the summer when University of Illinois students head home. Grab a cheesy bite of nostalgia at Papa Del's Pizza or enjoy more upscale fare at Bacaro; take time to admire the works at Krannert Art Museum and Spurlock Museum; go for a stroll at the University of Illinois arboretum (pictured) or Allerton Park and Retreat Center.
It's just a train ride from Chicago, but Woodstock feels anything but suburban. The historic town square (famously featured in Groundhog Day) is adorable, with great home decor shops, a cozy bookstore and the perfect lunch spot, La Petite Creperie. Come for the Woodstock Mozart Festival in early August or the farmers market—or the annual Groundhog Day Festival in early February.
Experience landscape that once rolled across the Midwest like an ocean at this restored prairie. Spot birds, hear frogs, hike and bike, see wildflowers and unwind among the 19,000 acres.
Though it’s home to the Fighting Irish, it’s not all football in South Bend. The St. Joseph River provides a great place for water sports and serves as a sparkling backdrop for a weekend of shopping and dining in the hometown of the University of Notre Dame.
Settled in 1834, Glen Ellyn prides itself on its leafy downtown, which straddles the Metra train line. The six-block downtown would fill a day for girlfriends on a getaway. Have breakfast at Honey; linger over handbags and jewelry at scrappy-cute AliKat; explore a vintage candy shop; and grab dinner before a movie at the historic Glen Art Theatre.
A great weekend destination for both shoppers and history buffs, Cedarburg has a Main Street that's on the National Register of Historic Places and dozens of limestone buildings housing more than 70 boutiques, chocolate shops and restaurants. Explore the town's history at the General Store Museum and Kuhefuss House Museum, and admire handiwork at the new Wisconsin Museum of Quilts and Fiber Arts. The town especially sparkles at Christmas!
Every day, hundreds of drivers speed past the turnoff on US-20 for Apple River Canyon State Park, bound for getaways in Galena. Those travelers admire the view from the car, not realizing that if they wanted a peek at one of the area’s few remaining secrets, they should turn north on Canyon Park Road west of Stockton and drive for just 7 miles. The 297-acre Apple River Canyon State Park offers quiet amid the woods along Apple River. Hike the bluffs. Look for fossils. Listen for wildlife. Fish the river—and let the others head to Galena.
This resort town of 7,600 has draws for summer and winter. Hotels, resorts and restaurants hug the lakeshore. Most visitors loll on the beach or cruise the lake during summer, but you can also experience the warmth of its winter in February during the annual Winterfest.
Sun, sand and.. race cars? Most people come here for quiet weekends of swimming, sunning, boating and water-skiing in the crystal-clear lake, but the legendary Road America course is popular with amateur racers and their fans. Nearby Kettle Moraine State Forest also offers outdoor rec of another type with trails for biking, hiking and running. Round out the weekend with a stay in one of the area resorts such as the Osthoff (pictured).
Famous for The Ephraim Faience Pottery Studio and Gallery, Lake Mills also offers plenty of outdoor recreation on Rock Lake, the Zoloski Marsh and the Glacial Drumlin Bike Trail, as well as a cozy Arts and Crafts style B&B. Snack on crackers and sip wine at Lewis Station Winery, and don't miss the old-fashioned James J. Chocolate Shop.
Apple picking, winery tours and cottage-style accommodations characterize this region, perfect for a fall getaway from Chicago.
Take a day to explore this Wisconsin bedroom community on Lake Michigan. A hearty breakfast at Franks Diner will fuel tours of the lakefront, the new Civil War Museum or the Anderson Arts Center, which hosts free Tuesday-night jazz concerts in summer. Dinner at Mangia Trattoria is a must; try the gnocchi. (800) 654-7309; kenoshacvb.com 
Purdue University injects energy into an area with a vintage feel: Buildings from 1900s line downtown. There are three distinct districts: the energetic campus area, a riverfront with parkways and town square, and east end with quaint shops and eateries.