Indiana's 'Gateway To The Dunes' Is An Artsy Tucked-Away Town With A Vibrant Downtown Market

If you've ever heard the tagline, "There's more than corn in Indiana," Chesterton is the town for you. Just an hour southeast of Chicago and under 10 minutes from Indiana Dunes National Park, Chesterton is a creative community with easy access to both nature and the city. You can visit on a scenic road trip from Chicago via Interstate 94 or U.S. Route 20, or skip the traffic with Chicago's South Shore Line train – you'll want to exit at the Dune Park stop.

Chesterton has long been known as the "Gateway to the Dunes" for its proximity to Indiana's sandy lakeside national park, but it's also built a reputation as a haven for artists and photographers. Stroll along streets filled with galleries, boutiques, and local cafés, where you can sip a latte while watching the South Shore Line rumble by. The town's compact, walkable layout makes it perfect for a weekend getaway — it scored a 73 "Very Walkable" rating from Walk Score — whether you're looking to escape the hubbub of Chicago, simply enjoy a few of Indiana's idyllic beach communities, or revel in one of America's most endangered national parks.

If you travel to Chesterton between May and October, the European Market is a must-see. Every Saturday morning for six months of the year, downtown Chesterton comes alive with 90 vendors selling everything from local restaurant fare and fresh flowers to handmade ceramics and original artwork. Live music adds to the ambiance throughout the season, and you'll be hard-pressed to leave empty-handed!

Make sure you grab an artisan pastry or some small-batch cheeses to munch while you shop. Many artists set up booths to sell their work, allowing visitors to get up close to the creative community that thrives in Chesterton. Even outside of market season, the local cultural scene remains lively, with the Chesterton Art Center (CAC) hosting exhibits and workshops all year. The Chesterton Art Fair, which celebrated its 66th anniversary in 2025, takes place the first full weekend in August and is one of the CAC's hallmark events. Other annual occurrences include the Corkscrew & Brew winery and brewery festival in March, downtown trick-or-treating in October, and the summer Moonlight Movies series in Chesterton Park.

Chesterton's artistic spirit extends well beyond the European Market. Along Broadway, you'll find Chelle's Boutique & Garage, a locally owned gem featuring women's apparel, gifts, and restored antique home goods, and Here Comes the Dress, a go-to for reasonably priced wedding gowns and formalwear. If you visit during the holiday season, the annual Mistletoe Market takes the place of the European Market, transforming Thomas Centennial Park into a festive showcase featuring local artisans and seasonal treats. Between shopping stops, fuel up at artsy, independent cafés like Fluid Coffee Roasters, which offers craft lattes and regular Meet the Author events; Red Cup Café & Deli, known for its Bohemian décor; or Third Coast Spice Café, which serves up wholesome dishes designed for everyone from vegans to meat-lovers.

For overnight stays, you can opt for local spots like Furness Mansion at the Dunes, a historic mansion-turned-boutique hotel, or standard mid-range choices like Hilton Garden Inn, Best Western, or Quality Inn. Rates generally run between $100 and $160 per night, depending on the season. Summer is peak time for Dunes visitors, but late spring and early fall offer lighter crowds – Michigan's Warren Dunes State Park is another underrated option if you want to enjoy the beach without throngs of people. Bring comfortable walking shoes for exploring, a camera for both the dunes and downtown, and a tote bag for your market treasures. Whether you come for the lake views or the art scene, any getaway to this region is sure to be memorable!