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

⮕ Hike Sand and Shorelines at Indiana Dunes State Park

Hike Sand and Shorelines at Indiana Dunes State Park

© S Quintans/stock.adobe.com

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

⮕ Explore Nature’s Beauty at Coffee Creek Watershed Preserve

Explore Nature’s Beauty at 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

⮕ Wander Through Wetland Wonders at Cowles Bog

Wander Through Wetland Wonders at Cowles Bog

© schankz/stock.adobe.com

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:

⮕ If You’re Craving Classic Eats, Grab a Bite at George’s Gyros Spot

If You’re Craving Classic Eats, Grab a Bite at George’s Gyros Spot

© 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

⮕ Roll Up for Retro Fun at Port Drive-In

Roll Up for Retro Fun at Port Drive-In

© Milan/stock.adobe.com

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

More Places to Eat in Chesterton, IN

  • Octave Grill – Local favorite for gourmet burgers, inventive sandwiches, and craft beer.
  • Lucrezia Café – Cozy Italian restaurant offering pastas, seafood, and outdoor patio dining.
  • Third Coast Spice Café – Great spot for creative breakfast, lunch, and vegan-friendly dishes.

If you are interested in local events:

  • Chesterton Art Fair (August) – One of Indiana’s top art festivals featuring regional artists, food vendors, and live music.
  • Chesterton’s European Market (May–October) – Weekly Saturday outdoor market with local goods and entertainment.
  • Hooked on Art Live Street Art Festival (September) – Celebrate creativity with live mural painting, food trucks, and family activities.

If you are looking for unique day trips within 30 Minutes of Chesterton, Indiana:

  • Michigan City (20–25 min) – Visit Lighthouse Place Premium Outlets, Washington Park Zoo, or the Indiana Dunes beaches.
  • Valparaiso (15–20 min) – Explore a lively downtown with shops, dining, and the beautiful Central Park Plaza.
  • Beverly Shores (10–15 min) – See historic homes from the 1933 World’s Fair or enjoy secluded beaches.
  • Portage (15–20 min) – Visit Portage Lakefront and Riverwalk, a peaceful spot for beach walks and sunsets.
  • Ogden Dunes (10–15 min) – Explore charming lakefront communities and hiking trails along the dunes.
  • Indiana Dunes Visitor Center (5–10 min) – Plan hikes, beach visits, and learn about the park’s ecosystems and history.

Frequently Asked Questions:

  • Where is Chesterton located?
    • Located close to the shores of Lake Michigan, just 50 miles southeast of Chicago, Chesterton is a leafy suburb and an ideal day-trip destination.
  • Why is Chesterton popular among outdoor enthusiasts?
    • 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.
  • What outdoor activities can visitors enjoy in Chesterton?
    • Each of these outdoor recreational areas offers excellent hiking trails and brilliant bird watching.
  • What can visitors do at Chesterton’s European Market?
    • 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.
  • Are there wineries in Chesterton?
    • Wine lovers can visit a few of the local wineries for a tour and tasting.

At a Glance:


Best Time to Visit Places to Stay Tips for Visiting
Spring (March-May) – Mild temperatures and blooming wildflowers. Waterbird Lakeside Inn – A peaceful stay with lakeside views. Explore Coffee Creek Watershed Preserve – Enjoy scenic walking trails and wildlife viewing.
Summer (June-August) – Warm and perfect for outdoor activities. Hilton Garden Inn Chesterton – A comfortable stay with easy access to the Indiana Dunes. Visit Indiana Dunes National Park – Hike, swim, or relax on the sandy shores of Lake Michigan.
Fall (September-November) – Crisp air, fall foliage, and fewer crowds. Best Western Indian Oak – A cozy hotel with beautiful autumn lake views. Attend the European Market – Enjoy local crafts, artisan goods, and seasonal treats.
Winter (December-February) – Quiet and scenic with snowy landscapes. Quality Inn Chesterton – A budget-friendly option for winter travelers. Explore the Indiana Dunes in winter – Enjoy snowshoeing or photography in a serene setting.

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