Chesterton
Travelers in a hurry tend to rush straight up I-65 on their way to Chicago, but the road less traveled offers a much more interesting exploration of “The Region.” North of Lafayette, the landscape presents an intriguing contrast, punctuating stretches of rolling farmland with fields of spinning turbines. Continuing on, the terrain shifts again into swaths of wetlands known as the “Everglades of the North.” The nearly 2,000-acre Grand Kankakee Marsh County Park near DeMotte lends itself nicely to deer, duck, and wildlife habitats, making it a popular destination for hunting, fishing, and bird-watching.
A little further up the road, Valparaiso rolls out a nice choice of restaurants and brewpubs for refueling (don’t forget to snap a selfie next to the statue of folksy Hoosier popcorn king Orville Redenbacher in Central Park Plaza). Wander green spaces and marvel at the working model trains that run through Gabis Arboretum at Purdue University Northwest’s enchanting Railway Garden before the exhibit closes for the season October 31.
At the end of the journey, the Indiana Dunes National Park on the shores of Lake Michigan makes a worthy road-trip reward, especially when it’s saturated in autumn color. Get out of the car and do a little hiking; Paul H. Douglas Trail in Miller Woods, Cowles Bog Trail, and Chellberg Farm all serve up especially scenic views. Feeling extra spry? Tackle the 3 Dune Challenge at the Indiana Dunes State Park to enjoy sightlines all the way to Chicago on clear days. If it’s too chilly for beach time, drive by and admire the historic 1933 Chicago World’s Fair Century of Progress Homes in Beverly Shores.
Now in its 23rd season, the popular European Market takes over downtown Chesterton on Saturdays through October, assembling an extensive collection of artists, makers, musicians, and food vendors. If you have antsy kiddos along for the ride, take a spin through Fair Oaks Farms on the way home for agriculture-themed learning opportunities, animal encounters, apple picking, cheese sampling, and other fun fall activities.
Shipshewana
Life moves slower in Amish Country, and that’s just fine. After zipping up I-69 through Fort Wayne, the exit onto U.S. Highway 33 toward Churubusco comes as welcome relief from highway driving, and the pace only continues to relax the further north you go. By the time you get to little Ligonier, the landscape opens into expanses of fresh-air farmland dotted with picture-perfect barns and modest homesteads.
You’re as likely to see horses and buggies as cars on the roads of Elkhart County, home to one of the largest Amish communities in the United States. Followers of the faith tend to eschew most modern amenities and conveniences (with some exceptions), preferring instead the peaceful simplicity of a quieter, more traditional way of life. To learn more, stop by the Menno-Hof information center in Shipshewana for a deeper dive into Amish culture and traditions. (Heads up: Don’t take any photos of Amish people without explicit permission; it violates a deeply held religious belief.)
If you have plenty of time, the self-guided 90-mile Elkhart County Heritage Trail driving tour is a lovely, relaxed way to get the lay of the land, traversing the rural communities of Goshen, Shipshewana, Middlebury, Bristol, Nappanee, and Wakarusa. With some overlap, the backroads route meanders past more than 100 cottage shops and 60 “barn quilts,” colorful hand-painted folk art plaques unique to each farm property.
Though the weekly Shipshewana Flea Market—at 40 acres, the biggest in the Midwest—wrapped up its 2026 season in late September, charming craft fairs and farm stands crop up in the fall to join evergreen area attractions like Goshen’s historic Bag Factory shopping center. The multipurpose Blue Gate complex draws visitors with a performing arts theater, a cozy inn, a restaurant, and a bakery. With home-cooked fare like roast beef, fried chicken, noodles, farm-fresh veggies, dinner rolls, and pie on the menu, you definitely won’t go hungry.
