Discover Waterfront Charm, Family Fun, And Miles Of Trails At A Lakeside Town In Indiana

While the big cities in the U.S. might attract the most tourists, there's something magical about visiting a small town and making it your home for a weekend or even a few hours. Fortunately, the Midwest is filled with tiny towns overflowing with charm waiting to be discovered. Rivaling any of America's most underrated small towns, Winona Lake, Indiana, is about to become your number-one travel destination.

Situated about two and a half hours outside Chicago, this waterfront town is home to approximately 5,000 people (according to the United States Census Bureau's 2020 Decennial Census). Rows of stately Victorian houses line the canals and waterfront, while Adirondack chairs, maples, and hickory trees dot the lawns. In fact, the entire scene is so picture-perfect it seems like a postcard. 

As the town's name implies, activities revolving around Lake Winona's waters are big draws. During the summer months, you can rent kayaks, paddle boards, and even pontoons from The Lake House or take a boat ride. For the anglers, Winona Lake is an ideal place to catch Smallmouth Bass (check the rocky areas), Northern Pike, Crappie, and walleye. If you have kids in tow, don't miss the Winona Lake Limitless Park and Splash Pad, a public park with free beach access, jungle gyms, and water features that make a lawn sprinkler look boring. However, strolling along the canal and stopping by the historic houses converted into shops and restaurants is also an unbeatable activity. 

Mountain biking enthusiasts and hikers can't miss the Winona Lake Trails, 10 miles of well-cared-for single-track trails, and walking paths that wind through the shady woods. If you're new to mountain biking or traveling with children, we recommend checking the map at the trailhead to find a section that fits your level, as well as getting familiar with the must-know hiking terms for your next outdoor adventure. The trail has three main access points — so you're never too far from civilization — but it's a good idea to pack extra water and a few snacks. During the summer months, the smell of honeysuckle lingers in the air, adding natural perfume to your outdoor adventure.

Another popular trail is the Lake City Greenway, which cuts through the center of town and circles the lake. Although it's not exactly one of the most epic hikes to take when visiting the Midwest, the path is paved and serves as an accessible option for families. The portion that snakes through the heart of Winona Lake is called the Heritage Trail. This 1.8-mile stretch of path displays works of public art celebrating the community, including sculptures and commemorative benches. 

Built in 1887 as a summer retreat, the Village at Winona is a collection of Victorian houses converted into boutiques, restaurants, salons, cafes, and inns. With a prime location along the canal and lakefront, the Village is the perfect place to take a leisurely stroll and do some window shopping.

Stop at the stationary store or pop into Belove to search for a trinket to commemorate your trip. Purchase handcrafted soap at Nine Pines Apothecary or join an olive oil tasting at The Olive Branch. After shopping, enjoy Asian-inspired dishes with a kid-friendly menu at Cerulean, and grab a scoop of ice cream at Social Ice Cream and Sandwich shop — try the churro flavor if it's available. Before planning your visit, check the Village at Winona's event calendar. From local art fairs to jazz festivals to fireworks displays, there's always something happening.

Get the full Winona Lake experience and spend the night in a historic home steps from the Village at Winona's famous facades. Choose from one of four beautifully appointed suites at Chestnut House Bed & Breakfast, a Princess Anne-style house with blue shingles and classic white trim.