Located close to the shores of Lake Michigan, just 50 miles south-east of Chicago, Chesterton is a leafy suburb which is an ideal day-trip destination. The area around Chesterton is a magnet for outdoor enthusiasts and nature lovers, who come here to visit the Indiana Dunes State Park, Bowles Bog and the Coffee Creek Watershed Preserve. Each these outdoor recreational areas offer excellent hiking trails and brilliant bird watching. If you visit on a Saturday (May to October) you can spend a few hours strolling around the Chesterton European Market, where you can meet local farmers and stock up on fresh produce and crafts. Wine lovers can visit a few of the local wineries for a tour and tasting. Hours/availability may have changed.

1.Indiana Dunes State Park

Indiana Dunes State Park
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Located between Chicago and Lake Michigan, the Indiana Dunes State Park is surrounded by the Indiana Dunes National Park and boasts a beautiful 3-mile stretch of beach along the edge of the lake. Beyond the beach you will find huge sand dunes which have taken thousands of years to develop. Some reach heights of 200 feet above the glimmering surface of the lake, offering a wonderful recreational area for nature lovers. Besides walking and hiking you can enjoy camping, swimming, smelt fishing and birding. Cycling is not allowed inside the park but cyclists can access the 9 mile Calumet trail which runs through the park. Guided activities include nature walks, owl prowls, stargazing and more.

Indiana Dunes State Park, 1600 N25 E, Chesterton, IN 16304, Phone: 219-926-1952

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2.Coffee Creek Watershed Preserve

Coffee Creek Watershed Preserve
© Coffee Creek Watershed Preserve

Home to over 157 acres of diverse habitats including wetlands, woodlands and prairie, the Coffee Creek Watershed Preserve is a magnet for nature lovers. The preserve welcomes visitors to explore a network of trails, including the 3-mile perimeter loop trail, which is suitable for walking/hiking and bird watching. If you visit between spring and fall you will be treated to a wonderful display of wild flowers, and any time of the year offers great photographic and fishing opportunities. The preserve hosts a regular calendar of workshops, classes and guided hikes and volunteers can participate in various stewardship projects including bird monitoring.

Coffee Creek Watershed Preserve, NE corner of 1-80/90 and IN 49, Chesterton, IN 46304, Phone: 219-926-1842

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3.Cowles Bog, Chesterton, Indiana

Cowles Bog, Chesterton, Indiana
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Cowles Bog is named for the visionary ecologist Henry Chandler Cowles, who attracted international attention to this remarkable 4000-year old wetland complex in the Indiana Dunes National Park. The complex includes a variety of habitats including bog, fen, pond, swamp and wet-meadow areas, each of which attract a variety of birds, reptiles and small mammals. You can explore this wonderful natural asset by pulling on your hiking boots and setting off along the three loops which form the Cowles Bog Trail. Together, the trail covers 4.7 miles of wetland wonderland. Parts of the trail are quite steep as you make your way over the dunes – remember to bring your sunscreen, camera and plenty of drinking water.

Cowles Bog Trailhead, Main Lot N: 1450 North Mineral Springs Rd, Dune Acres, IN 16304

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4.Butler Winery, Chesterton, Indiana

Butler Winery, Chesterton, Indiana
© Butler Winery

Butler Winery is the 4th oldest winery in Indian, established in 1992 by Jim and Susan Butler. Although the vineyards are located outside Bloomington, the Butlers established a satellite tasting room in Chesterton, where visitors are invited to come and learn about their range of wines. The tasting room as a very pleasant outdoor terrace area where you can enjoy your tasting on good weather days. $6 will buy you a tasting flight of 6 Butler wines, a great introduction to the range, or you are welcome to order your favorites by the glass. The onsite wine shop sells all their wines as well as wine-lover’s gifts and much more.

Butler Winery, 401 Broadway, Chesterton, IN 46304, Phone: 219-929-1400

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5.Ivy’s Bohemia House, Chesterton, Indiana

Ivy’s Bohemia House, Chesterton, Indiana
© Ivy’s Bohemia House

Ivy’s Bohemia House Restaurant opened its doors in 2015, offering Chesterton locals and visitors a warm and relaxing environment where they can enjoy fresh, home-made food and old fashioned cocktails. Chefs Amy and Wayne bring an interesting choice of dishes to the menu, inspired by Amy’s Polish heritage and Wayne’s love of vegetarian food. You can expect to find delicacies like house-made Polish sausages for meat lovers and delicious black-bean burgers, falafel and pastas for vegetarians. In between the two extremes there are plenty of choices for all tastes, including specialty salads, their signature Polish Platter and mouth-watering pastas and sides.

Ivy’s Bohemia House, 321 Broadway, Chesterton, IN 46304, Phone: 219-929-4319

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6.George’s Gyros Spot, Chesterton, IN

George’s Gyros Spot, Chesterton, IN
© George’s Gyros Spot

Family owned and operated, George’s Gyros Spot has been pleasing Chesterton palates for more than 20 years. What started out as a small stand selling Gyros and hotdogs has grown by leaps and bounds and the restaurants new premises can now seat 100 diners. On the menu you will find their signature Gyros, served with pita, fresh onions and tomato and a side of fries. Besides the ever-popular Gyros you will find a wide selection of hotdogs, sandwiches, burgers and wraps. In addition there are delicious baskets of chicken nuggets or tenders, shrimp, cod and buffalo bites. Remember to leave some space for a delicious ice cream dessert.

George’s Gyros Spot, 325 N Calumet Rd, Chesterton, IN 46304, Phone: 219-926-5435

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7.Port Drive-in, Chesterton, Indiana

Port Drive-in, Chesterton, Indiana
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Dating back to 1953, The Port Drive-in has been a popular landmark in Chesterton. The Port is famous for serving up legendary chilli dogs and frothy mugs of old-fashioned root beer. For a nostalgic trip down memory lane you can still treat yourself to these 50’s classics, served right to your car, just as they have done for over 50 years. Today visitors to The Port have the choice of dining inside, in an air-conditioned dining hall where you can choose from a much-expanded menu which includes sandwiches, wraps, burgers, dogs and sides. Drinks and desserts include floats, milkshakes, old-fashioned sundaes and classic dipped cones.

The Port Drive-in, 419 N Calumet Rd, Chesterton, IN 46304, Phone: 219-926-3500

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7 Best Things to Do in Chesterton, Indiana

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