7 Very Worthwhile Midwest Weekend Getaways

For residents in the Midwest states, it can seem like there aren’t many places to go aside from the big cities. Outside of cities like Chicago, Cleveland, St. Louis, and Milwaukee, towering skyscrapers give way to strip malls and suburbs and then it’s just cornfields and cow pastures as far as the eye can see, right? Wrong.

The Midwest is actually fun of charming small towns that are the perfect foil to life in the big city. With good food, fresh air, lively town squares and friendly people, they’re miles away from “podunk” and an ideal antidote for urban burnout. If you live in the Midwest and are looking for new weekend destinations, or you’re visiting from elsewhere and want to combine your time in the cities of the region with some day or overnight side-trips, check out these easy-to-reach destinations that make for a perfect short break from the city.

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New Buffalo, Michigan

newbuffaloAn hour from Chicago and around four hours by from Detroit by car, the west coast of Michigan is dotted with lakeside towns like New Buffalo, Saugatuck, and St. Joseph. Each one has its own charms, but all offer stunning Lake Michigan sunsets, swimming and boating on the lake, and plenty of family fun.

New Buffalo, a small town that can easily be navigated on foot, is a popular vacation spot for many city dwellers and has that posh “resort town” feel – you’ll see plenty of yachts floating in the harbor and find no shortage of upscale dining and drinking opportunities. Saugatuck, with its beautiful beaches and proliferation of art galleries, is a popular retreat for the both the gay crowd and families alike. And St. Joseph, the sleepiest of the towns, is perfect for those truly looking to escape.

Aside from the shores of Lake Michigan, the main draw in the area is the Southwest Michigan Wine Trail, a collection of a dozen wineries that are open to the public for tastings. You can drive yourself or hire a car-service for the day. Be sure to stop at Round Barn Winery, where you can tour the facilities, have a picnic lunch, and even take a wine-making class.

>> Search for flights to Chicago and find hotels in Chicago

Lake Geneva, Wisconsin

lakegenevaFor a romantic getaway, Lake Geneva is ideal. Fifty miles from Milwaukee and 90 from Chicago, the lake is dotted with small towns and luxury resorts. The Abbey, a full-service resort, will even pick up guests from the Harvard Metra train station (which welcomes trains from Chicago hourly), so city-dwellers without a car can still get there easily. The resort offers a full-service spa, games for the kids, live music and barbecue on weekends, water-sports on the lake, and a nearby beach.

The town of Lake Geneva itself is the launching point for boat tours of the lake, which will take you past the multi-million dollar lakefront homes owned by some of the biggest names in industry. The town was pretty much founded by the rich and elite, and in its heyday was a party destination for movers and shakers in the Midwest (there was even a Playboy Club here at one time).

Yet despite the wealth of the families that live on the lake, the area still retains a very accessible, unpretentious feel. Just a bit down the shoreline from some of the biggest houses, a public harbor and beach ensure that those who live on more modest means can still have access to the lake. Residents are also required to maintain a two –foot walkway on their lakefront, so you can walk full-circle along the lake’s shores if you choose.

>> Search airfare to Milwaukee and read about things to do in Milwaukee

Galena, Illinois

galenaThe three-hour drive from Chicago to Galena, across the Mississippi River from Iowa, will take you through some of the most beautiful country in Illinois. Galena itself is just as lovely. Well-preserved historic buildings – around 85% of the town’s buildings are listed on the National Register of Historic Places – line the brick streets.

A walk down Main Street will take you past a church built in 1832, as well as the oldest-operating hotel in Illinois, the Desoto House Hotel. You’ll also find several dining options and the Galena Cellars Tasting Room, where you can sample wine produced at the nearby winery.

Galena is one Midwest destination that is just as popular in winter as it is in the warmer months. That’s because nearby you can ski at the Chestnut Mountain Resort or golf, fish or ride horses at the Eagle Ridge Resort and Spa. If those are bit of out of your price range, you’ll find plenty of more affordable options. Galena is home to over one hundred family-run bed and breakfasts that offer a more-low key stay at a smaller price.

Madison, Wisconsin

madisonFour hours from Minneapolis/St. Paul and less than two hours (by bus or car) from Chicago or Milwaukee, Madison is populated by over 200,000 people. Yet Wisconsin’s capital, and the second-largest city in the state, still manages to feel like a small town.

It is home to the University of Wisconsin-Madison, and has a very youthful feel, with hundreds of college bars, live-music venues and cheap places to eat scattered around the city. In summer months, the city really comes alive with Saturday farmers markets, outdoor concerts, music festivals, and boating on the four lakes that surround the city.

The Great Taste of the Midwest craft beer festival, held each August, is one of the city’s most popular events – tickets for the festival often sell out the first day they go on sale – and the Rhythm and Booms Fourth of July fireworks display is the largest in the Midwest. During winter months the lakes freeze and, despite the cold, you’ll find hundreds of people out ice-skating, ice-fishing and cross-country skiing.

>> Book flights to Minneapolis and find St. Paul hotels

Traverse City, Michigan

traversecityFour hours from Detroit and five hours from Chicago by car (though you can fly into the local airport from either city as well), Traverse City is known as the “Cherry Capital of the World” and hosts an annual Cherry Festival each summer. The town is one of the most popular destinations in Michigan and it’s easy to see why. The waters of Lake Michigan, 180 miles of sandy beaches, and verdant forests surround the town with natural beauty, while acres of golf courses and ski slopes provide endless year-round outdoor fun.

In addition to the Cherry Festival, the historic downtown also hosts a Film Festival founded by Michael Moore, art shows, music festivals, and farmers markets. Sleeping Bear Dunes, massive sand dunes that rise from the shore of Lake Michigan, are nearby, along with several hiking and biking trails.

Driving outside of Traverse City in the warmer months, one might even mistake the region for Tuscany, or at least California’s Napa Valley. The area is home to nearly 30 wineries and the rolling hills of a vineyard, its vines heavy with grapes, is a common sight. Nearly all of the wineries are open for tastings, so you can enjoy a day of wine tasting hopping from winery to winery, or just head to one of the tasting rooms located around the town square.

>> Find flights to Detroit and book Detroit hotels

Door County, Wisconsin

doorcountyDoor County, on an isthmus in the far northeast of Wisconsin, is two hours from Milwaukee and four hours from Chicago by car. A ferry also makes a four-hour journey across the lake from Michigan in the summer.

The standard assortment of resort town activities are here – swimming, biking, sailing, canoeing, horseback riding and fishing – but the area is also well known for its many man-made attractions that cater to families with younger children. There’s a zipline adventure through the trees, parasailing, mini-golf, tubing, and a petting zoo. To keep adults happy while the kids are entertained, you’ll also find several day spas, scuba diving in Lake Michigan, and five nearby wineries.

Door County is at its busiest in summer, so to avoid the crowds and kids, come in late spring, for the Festival of Blossoms, or in fall when the leaves are ablaze in bright orange, red and yellow. There’s still plenty to do in winter too. It’s cold, but skiing, snowshoeing, snowmobiling and riding a horse-drawn sleigh will keep you warm.

Long Grove, Illinois

longgroveFor a shorter break, the historic village of Long Grove is just 30-minutes by car or train from Chicago, and can be covered in one day or less. The town almost has a “Main Street USA” feel. The cobbled streets and brick sidewalks lead to a perfectly landscaped central square and the mom-and-pop shops, many of which are located in historic houses, hearken back to an older, simpler time.

The Apple Haus is famous for its-fresh made donuts, Long Grove Confectionary will satisfy any sweet tooth, and Seasons of Long Grove serves a traditional English tea-service and an elegant Sunday brunch. The town also hosts a full calendar of community events like Oktoberfest, Irish Days, and the Wine, Dine and Art Fest.

Looking for more weekend travel ideas? Check out seven great American road trips for a long weekend

Photo credits:
New Buffalo by pandabrand on Flickr, Lake Geneva by Luiz Castro on Flickr, Galena by thomas.merton on Flickr, Madison by JanetandPhil on Flickr, Traverse City by Bernt Rostad on Flickr, Door County by Ted Ingraham on Flickr, Long Grove by puroticorico on Flickr

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