Need a relaxing getaway near Lake Michigan? Head to Chesterton! Nestled by Indiana Dunes National Park, Chesterton offers scenic outdoor adventures, charming downtown streets, local art, and easy beach access. Whether you're hiking, shopping, or soaking up small-town charm, Chesterton is a delightful Midwest escape.
Chesterton, IN Highlights:
- Indiana Dunes National Park: Explore over 15,000 acres of sandy dunes, beaches, and diverse hiking trails along Lake Michigan.
- Chesterton’s European Market: Enjoy a vibrant seasonal outdoor market featuring local produce, crafts, food, and live music (May–October).
- Coffee Creek Watershed Preserve: Walk scenic trails, boardwalks, and gardens in this peaceful nature preserve.
- Indiana Dunes State Park: Swim, sunbathe, hike the rugged "Three Dune Challenge," or picnic near the lakeshore.
- Historic Downtown Chesterton: Browse local shops, galleries, restaurants, and cozy cafés in a charming downtown area.
Best Time to Visit Chesterton, IN
The best time to visit Chesterton is in the late spring through early fall (May–October). Enjoy warm beach days, outdoor festivals, and beautiful hikes. Fall is especially lovely for colorful foliage and cooler hiking weather.
How to Get to Chesterton, IN
- If you are traveling by car: Chesterton is conveniently located off I-94 and the Indiana Toll Road (I-80/I-90), about 1 hour southeast of Chicago.
- By Train: South Shore Line commuter trains connect Chesterton (via nearby Dune Park Station) to downtown Chicago and other northwest Indiana towns.
- By Plane: Chicago Midway International Airport and O'Hare International Airport are both about an hour to an hour and a half away by car.
Where to Stay in Chesterton, IN
- Spring House Inn – Cozy rustic lodge surrounded by woodlands, perfect for a relaxing stay near Indiana Dunes.
- Hilton Garden Inn Chesterton – Modern amenities, indoor pool, and easy access to highways and parks.
- Waterbird Lakeside Inn – Scenic hotel offering lake views and peaceful accommodations close to downtown Chesterton.
Best Things to Do in Chesterton, IN
1. Hike Sand and Shorelines at Indiana Dunes State Park
Rating: ★★★★★
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
2. Explore Nature’s Beauty at 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
3. Wander Through Wetland Wonders at Cowles Bog
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
Where to Eat:
4. If You’re Craving Classic Eats, Grab a Bite at 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
5. Roll Up for Retro Fun at Port Drive-In
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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