The Art of Living in Chesterton

Indiana Dunes

Story by Elizabeth Granger

Chesterton is a destination for the arts, specialty shops, dining, train, history, & the dunes on Lake Michigan.

Kay Cherepko didn’t grow up in Chesterton. But, she says, it feels like she did because her family visited so often. She talks of Christmases and parades and snow falling on the bandstand in the park and says it’s “like being in a Hallmark movie.” 

Cherepko owns the Flying Mermaid on South Calumet Road in Chesterton. It’s beachy/vintage/consignment, with a lot of mermaids. It’s the Flying Mermaid because “when we opened, we were flying by the seat of our pants.” 

Behind her shop, tucked into the back of the building, is ArtZ: fine ArtZ & antiqueZ. Co-owner Bridget Nadolski calls it “a dream that came true.” That dream? “I would like to have a gallery,” the retired art teacher said years ago. “I would like to gather all my art friends together and I would like to sell their work and support them and have a working studio.” ArtZ celebrates its third anniversary this summer.  


“This town supports its artists,” she continues. “They value having art in this town.” 

There’s more than one gallery, often with classroom space. One is the Chesterton Art Center on South 4th Street. 

“We’ve always been an artsy community,” says Wendy Marciniak, president and CEO of the center. “The dunes have a lot to do with it. They’ve always inspired people to come out and paint. This community has always been proud of its arts.” 

The motto for the town of 14,000 is “the art of living.” The European Market on summer Saturdays is ultra-popular with foods, clothing, fresh produce, flowers, live entertainment – and art. In late July it will be joined by the Upsadaisy Market on Sundays, which will focus more on up-scale juried art. The Coffee Creek Farmers’ Market is on Wednesdays, a vintage car show the last Saturday of each month. The Chesterton Art Fair is Aug. 7-8, the Hooked on Art Street Festival Sept. 18. 

ArtZ’s Nadolski calls Chesterton “a destination.” In addition to the arts, there are specialty shops, restaurants, breweries, wineries, the beach on Lake Michigan, birding, biking trails, the trains. 

Ah, the trains. There’s more than a century of rail history here, and today more than 90 trains go through town each day. “And no one complains,” Nadolski says. 

“We are a destination for a lot of train buffs,” says town manager David Cincoski. “We have five railroad crossings in town, and a day doesn’t go by that people will stay all day and watch and record trains go by all day long.” 

Rail fans, they’re called. Or train nerds. Or maybe even train nuts. You’ll find them at crossings with cameras and notebooks and information to share. Sometimes they stay at Riley’s Railhouse, a bed-and-breakfast in an old freight depot. Guests sleep in the depot or in rail cars on tracks just outside. 

European Market

One of those guests is Timothy Allen of Cincinnati. “I’ve been a rail fan my whole life,” he says. “It’s fun to sleep next to the trains; they actually shake the building. There’s so much cool railroad stuff here.” 

The town’s public restrooms, a few steps from that Hallmark-like bandstand, are revamped rail cars. 

Others choose biking; Chesterton’s biking trails connect to a myriad of trails that can take cyclists throughout northwest Indiana and into the Chicago area. 

“Downtown is a bit of a jewel,” says Kevin Nevers, Chesterton’s public affairs liaison. Specialty shops are primarily along Broadway and South Calumet Road. Many of the quaint downtown buildings were built after the 1902 fire with bricks from the local brickyard. 

Walk into the past at O’Gara & Wilson Antiquarian Booksellers on Broadway – it’s been around for close to 140 years. Owner Doug Wilson grew up in Chicago. “I wanted to be from Chesterton, but my father wouldn’t move when I was a kid,” he says. “We used to go to the dunes and we’d pick up our picnic food here.” 

The bookstore is full of vintage items, old documents, history. “It’s for people who want to discover,” Wilson says. “To their delight, they find a book they didn’t know existed. This store is for people who want some serendipity in their life.” 

Continue to re-live the past at any of the antique and what-nots stores. Let yourself be lured by Oh Gee Doughnuts or Dog Days Ice Cream Parlor, both on South Calumet. Three Moons Fiberworks, in the old post office, is all about weaving and knitting and everything else yarn. 

And Chesterton Toys is full of old-fashioned fun. “We promote kid power, imaginative play, not too much with batteries, ages 0 to 99,” says co-owner Zach Kinsey.  Generally, items that can’t be found in a big box store. 

About a mile down South Calumet is Sweet Stitches Quilt Shop where owner Joan Crookston uses her art background to advise customers. “A lot of people struggle with colors,” she says. “I love working with color.” 

She also loves steering customers to other Chesterton sites, including the dunes on Lake Michigan. “We’re just 3 miles away,” she says. 

It’s where visitors will find Indiana Dunes State Park, which is surrounded by Indiana Dunes National Park. It was formerly called Indiana Dunes National Lakeshore; in 2019 it became America’s 61st national park. Nevers calls it “a string of pearls” with nooks and crannies “cobbled together over a period of years.”  

Because of the lake and its iconic dunes, Chesterton and its surrounding area is known as Duneland. Lake Michigan has long been a draw for artists, beach lovers, campers, hikers, cyclists, fishermen, birders…Just add shopping, dining, lodging.