City in the Spotlight: Chesterton

Nestled between the Indiana Dunes and Coffee Creek, the Town of Chesterton has managed to maintain its small-town, historical feel while providing all the modern amenities a person could wish for. From dining downtown at eclectic eateries to fun festivals in the park with family and friends, Chesterton is a town that never stops giving.

Check out some of our favorite things to do while visiting Chesterton before scheduling your own trip!

Dining

Lucrezia Cafe

If delicious Italian in an intimate setting is the vibe for tonight, Lucrezia Café in Chesterton can be the end of your search. Located along Calumet Road, Lucrezia’s easy access location is only the first in a long list of reasons to make a stop at the café. With a wide range of food and wine on offer, a visit to 428 S. Calumet is a no-brainer the next time you’re in town.

Musashi

Chesterton’s Musashi restaurant and sushi bar has high-quality meals at wallet-friendly prices. Nestled right off of State Road 49, you can dine with your friends and family on authentic Japanese cuisine. Everything from filet mignon and salmon to scallops and shrimp are prepared before your eyes on the hibachi. If you’re in the mood for sushi instead, Musashi has over 80 rolls ready to be ordered. Make a visit to 757 Indian Boundary Rd. a must on your trek to Chesterton.

Root & Bone 

Root & Bone offers up a huge helping of southern hospitality with a side of culinary artistry to create a dining experience unlike any other. Fried chicken, spare ribs, brisket meatloaf –  if it’s delicious, you can find it in Root & Bone’s kitchen! Led by two nationally recognized chefs, Root & Bone brings a little bit of the South to Chesterton with every meal. Swing by 600 Gateway Blvd to see for yourself!

Dog Days

During the dog days of summer, nothing hits the spot quite like a large ice cream cone from the ice cream parlor. Dog Days in Chesterton offers cups, cones, and shakes in a diverse range of flavors, from classics like chocolate and vanilla to seasonal treats like caramel apple pie! When the sun is high in the sky and the temperature keeps rising, check into 123 S. Calumet Rd. to refresh.

Sights

Indiana Dunes State Park

One of the ecological gems of Indiana, the Indiana Dunes are a look back into a younger land before the cities and towns began to rise. With trails passing through this incredible natural environment open to the public, you can discover the wildlife of Indiana and connect with the world around you in a way that’s impossible to find elsewhere.

Coffee Creek Preserve

Featuring almost 160 acres of pristine natural landscape, Coffee Creek Preserve is the perfect escape for nature lovers. Known best for its birding opportunities and the beautiful wildflowers blooming spring through fall, the preserve has hiking trails, event spaces, and amenities that help make your visit pleasant every time.

Westchester Township History Museum

For those who prefer to take their advantages via the written word, the Westchester Township History Museum highlights local history spanning from the first humans walking through Chesterton to the modern innovations keeping the town front and center in the Region. The museum has several permanent exhibits and offers a suite of other services for the amateur and the professional historian, including research assistance and genealogical records.

Things to Do

European Market

Chesterton’s European Market is a local tradition that’s grown into a phenomenon. Every Saturday from May through October sees downtown Chesterton transformed into a shopping spree right out of your dreams. Artisanal crafts and baked goods will catch your eye and make your mouth water. Purchase your new favorite shirts, artworks, and more when the market is in town!

Bike Trails

The Town of Chesterton’s bike trails take full advantage of the town’s location along several natural environmental gems. The Prairie-Duneland trail runs 3 miles from 15th St. to State Road 149, while the Westchester-Liberty Trail connects Chesterton to the Dunes Kankakee Trail for the Chesterton Loop. Burn rubber as you race through the Dunes to your next adventure!

Pickleball

The Region’s latest craze is alive and well in Chesterton! Chesterton Park has its own dedicated pickleball courts to help you improve your game and flex your skills against your friends. Programs involving adult pickleball, including tournaments and lessons, can make an appearance in the Parks Department’s schedule. Keep your eyes peeled for your chance to grab your racquet and hit the court!

Running Vines

At the end of the day, a relaxing glass of wine with your friends is the perfect way to cap off your time in Chesterton. Running Vines Winery is family-owned and operated with a dedication to providing a relaxing experience every visit. Whether you’re dropping in for a tasting or joining one of the frequent trivia nights, you’ll always find yourself in good company.

Events

Third Fridays

When the weather gets nice, the third Friday of every month in Chesterton brings something new to visitors and residents alike! During Third Fridays, downtown Chesterton retailers, artists, and vendors offer special deals and treats that encourage everyone to explore what Chesterton has to offer. Get ready for next season to begin now so you’re prepared come May!

Winter Market

When winter blows in with its chill and snow, the European Market transforms into the Mistletoe Market! This special holiday-themed market helps you grab all of your winter necessities: ornaments, gingerbread, jewelry, sweaters, and more. In addition to the special goods, celebrate the upcoming winter holidays with a tree lighting and the annual Twilight Parade!

Chesterton Art Fair

The Town of Chesterton has always prided itself on its vibrant arts community, and this is seen nowhere more than in the town’s annual Art Fair. For over six decades, the Chesterton Art Center has brought together local artists for a day-long festival celebrating the Region and the inspiration it provides with its unique atmosphere, culture, and ecology. If you’re a lover of the arts, the Chesterton Art Fair is a must visit when it comes to town!

Chesterton High School events

Chesterton High School offers the community a wealth of fun activities for everyone to enjoy. From football on Friday nights to robotics and Science Olympiad competitions, there’s something for everyone at the local high school. Keep up with everything happening by following our coverage of local events!

Did we miss your favorite part of Chesterton? Share it with us and to help us make our guide the best in the Region!