Take a Day Trip to Charming Winona Lake, Indiana—Just 2.5 Hours from Chicago and Indy

Before spending a day in Winona Lake, Indiana, make sure you learn how to say it: why-known-ah (like Judd) rather than wuh-now-nuh (like Ryder). Got that? Now you're ready to amble along the village's canal, paddle on its namesake lake and bask in its Victorian charm. Hundreds of lakes dot northern Indiana, but this town's a standout—and only 2.5 hours from both Chicago and Indy.

9 a.m. Brew and a Trail

Grab a cup of micro-roasted coffee from the Light Rail Cafe for a walk on Winona Lake's 1.8-mile Heritage Trail, part of the larger Lake City Greenway. Or utilize the area's bike-share program to pedal the paved path.

10 a.m. Shop in Canal-Front Cottages

At the heart of town, The Village at Winona is a collection of canal-front cottages that have been renovated into a commercial hub. Wander into pretty pastel shops like LetterWood Paper Company, which stocks hand-painted greeting cards. Get a dose of gourmet flavor at Canal Street Market, a luxe general store with a cozy front porch.

1 p.m. Boxed Lunch

Popular Pan-Asian eatery Cerulean offers a bento box-style lunch menu. Pick one entree, like Crispy Chili Beef or Spicy Lemon Shrimp, and pair it with three sides, such as Asian Noodles or Crispy Potatoes with roasted garlic dip. The restaurant also has an impressive sushi list.

2:30 p.m. Play on the Water

Get on the water with a kayak or paddleboard rental from The Lake House. The waterfront surf shop also rents pontoon boats by the hour or for full or half days. More interested in angling? Winona Lake is a natural lake with prime bass fishing, so you can cast away from the public pier.

5 p.m. Dinner with a View

Start with wine and cheese at Port Winona before strolling down the street to BoatHouse Restaurant. The expansive menu at this town stalwart features smoked pork chops and pretzel-crusted walleye. For the best seat(s) in the house, request a table on the lakeside porch.

8 p.m. Evening Glow

Settle in for the sunset from the east shore at Winona Lake Limitless Park. Bring a blanket and watch the stars surface—the cherry on top of a peaceful lake day. Want an actual sundae to usher in twilight? Grab a scoop from Social, a new spot opening in May.