Amtrak Train Day Trips from Chicago
New Buffalo, Michigan From the Amtrak station, it's a short walk to Third Coast Surf Shop (thirdcoastsurfshop.com) to rent kayaks and paddleboards to take out on Lake Michigan. Or just soak up the sun on the pristine New Buffalo City Beach. (Swimming is an option, too, if you can stand the perpetually chilly water.) In town, shoppers can browse boutiques, including Adelaide for chic designer clothes (adelaideusa.com). Bentwood Tavern is the place to admire a marina full of cabin cruisers while dining on garlicky shrimp and polenta, or pizza with toppings like prosciutto and fig (marinagrandresort.com).
Milwaukee's Walker's Point neighborhood On the city's south side (near the Milwaukee Intermodal Station), start-up entrepreneurs have embraced the gritty, century-old industrial buildings and filled them with appealingly unpolished eateries and shops. Warehouse-size Antiques on Pierce contains three floors of Depression glass, vintage posters and midcentury armchairs (antiquesonpierce.com). Just down the road, Central Standard Craft Distillery shows off its gin and vodka production on weekend tasting tours (thecentralstandard.com), and the next-door Milwaukee Brewing Company serves samples of its roasty stout on tours (mkebrewing.com). For dinner, try c.1880 for seasonal eats (perhaps pheasant with spaetzle and mustard) served in an industrial-chic dining room (c1880.com).
South Bend, Indiana If you've never visited Notre Dame, cross that bucket-list item off this year. Campus tours pass legendary sites like the Golden Dome, the stadium, "Touchdown Jesus" and the lesser-known "First Down Moses." It's worth an overnight to visit the candlelit grotto and experience the exceptional service of the four-diamond Morris Inn on campus (www.nd.edu/visitors). Dinner presents a tough choice between respected restaurants Corndance Tavern (corndance.com), where an endlessly inventive menu showcases local foods, and Cafe Navarre, an upscale eatery in a renovated bank building (cafenavarre.co).