Between Chicago And Indy Is A Charming Midwest Town With A Friendly Community And Tasty Local Eats

One downside to having two major cities like Chicago and Indianapolis within driving distance of one another is that the small but visit-worthy gems in between can get lost in their shadows, leaving travelers who want a quiet, crowd-free getaway struggling to find a destination. There's one charming Midwest town you might not have considered yet, though: Kentland. It's a community of just over 1,600 residents and exudes a quiet, friendly atmosphere. It's also family-oriented, and there's a general sense of safety. But don't take all that to mean that there's nothing to do and see around town.

While Kentland's charm is relaxed, the area is home to inviting locally-owned businesses, plus some highly-reviewed restaurants like Old Colonial Inn and Downtown Lounge and Trattoria. One of the best ways to take in the atmosphere is to attend one of the community events, many of which are organized at the Newton County Fairgrounds. The Newton County Pun'kin Vine Fair, in particular, might be worth tweaking your schedule for, since it's been a Kentland staple for generations.

Those who want to make the most out of the region's outdoorsy allure will be happy to learn that the town provides access to several parks. And because Kentland is surrounded by country roads perfect for driving, you can plan some great day trips as well. Many travelers will find driving here the most convenient option, especially since it isn't the most walkable destination. Kentland is also positioned almost perfectly between Chicago and Indianapolis (less than two hours from each), making both Chicago O'Hare International and Indianapolis International viable options for fliers looking for the nearest major airport.

Big cities often come with plenty of worthwhile day-trip options. Joliet, for example, is one of Chicago's most affordable suburbs and a town on Route 66 packed with Americana charm and shopping. But Kentland offers a kind of small-town atmosphere that's increasingly hard to find close to major metropolitan areas. Best Places even describes it as a peaceful, rural-feeling spot surrounded by green fields and rolling hills. 

Kentland's cozy allure is also owed to its locally owned businesses like Market No. 48, where visitors can browse decor pieces, floral arrangements, and gifts to take home. Google reviewers praise the kind, helpful owner, too, which fits the town's reputation for friendly locals. As accounts from both Niche and Nextdoor show, this is a place where people know each other's names and are willing to extend a helping hand, so don't hesitate to mingle and ask for some insider tips when needed.

Despite its small size, Kentland offers several noteworthy dining options. Old Colonial Inn is one of the top restaurants in the area according to Tripadvisor, and has been operating since 1964. It prides itself on its quality meats and seafood, with menu items such as roast prime rib, filet mignon, New York strip steak, lobster tail, salmon filet, and Alaskan king crab legs. Just around the corner, Downtown Lounge and Trattoria serves Italian-inspired fare, including sandwiches, pastas, and a variety of meat cuts. Patrons have complimented its fresh food, great service, and comfortable ambiance, with one noting that every dish they had "was bursting with flavor and cooked to perfection." If you're looking to explore farther afield, Crawfordsville makes for an appealing day trip. Dubbed the "Athens of Indiana," the city is known for its walkable, artsy downtown, unique museums, and historic sites.

One major perk of visiting a small town like Kentland is the abundance of green spaces sourrounding it. Cast Park is a great place to start your outdoorsy experiences. Its amenities include a walking path, playground equipment, indoor restrooms, a sledding hill, and even a catch-and-release pond that's child-friendly. The fountain and gazebo add to the picturesque feel, and the area is clean and well-lit. Visitors can come to enjoy a picnic and take in the quiet atmosphere.

Those looking for something more high-energy, on the other hand, can plan a visit around the Newton County Pun'kin Vine Fair. It usually takes place in mid-July and features everything from food vendors, rides, and harness racing to nearby camping opportunities, demolition derbies, and live entertainment. Held at the Newton County Fairgrounds, the fair is wheelchair-accessible, free to enter, and designed to celebrate the community and provide insight into its agricultural roots.

Indiana has the best quality roads in the entire country, and is even nicknamed the "crossroads of America," so take this opportunity to explore the countryside surrounding Kentland, as well. You won't even have to go off the beaten path. Brookside Park, for example, located in Rensselaer about half an hour away, features a swimming pool, softball and football fields, basketball and volleyball courts, a walking area, a playground, a disc golf course, and five picnic shelters equipped with electricity. Dogs are allowed, too. Kankakee Sands is another interesting spot to add to your itinerary. Also located between Chicago and Indianapolis, it's a nature preserve filled with bison, unique birds, and prairie views, and you can reach it in roughly 25 minutes from Kentland.