Leave New Chicago around 10:30 a.m. for Indiana Dunes National Park, roughly a 20–30 minute drive via I-94 and local roads, depending on traffic. Start with a scenic stretch of dune and lakeshore exploration—West Beach is a good choice if you want sand, broad Lake Michigan views, and a more substantial walk; allow about two hours. Parking can fill on pleasant September mornings, and a national park entrance fee may apply at some lots, so keep a card handy. Wear shoes with traction and bring water: dune climbs are short but surprisingly strenuous.
Continue to the Indiana Dunes Visitor Center in Porter for about 45 minutes. It’s the best place to get current trail advice, see the park’s natural-history exhibits, and check conditions before committing to a longer hike. It is generally open daytime hours, though September schedules can vary, so confirm the day’s hours before leaving; the exhibits and park information are typically free, while some parking areas may require a fee. From there, drive about 10–15 minutes into Chesterton for lunch and coffee at Uptown Cafe, a relaxed local stop where you can expect roughly $15–30 per person and about an hour at an unhurried pace.
After lunch, make the short drive to Coffee Creek Watershed Preserve, just a few minutes from central Chesterton. Spend around 1½ hours wandering its easy trails through wetlands, prairie, and wooded sections; it’s a pleasant contrast to the open dunes and does not require a strenuous hike. Trails are usually accessible during daylight, but surfaces can be muddy after rain, so sneakers with some tread are useful. Then continue about 15 minutes south to Valparaiso Downtown, where the historic central square and nearby shops make an easy late-afternoon wander. Give yourself about an hour to browse without trying to cover every block.
Finish at Industrial Revolution Eatery & Grille, a convenient choice near downtown Valparaiso for an early dinner. Plan on approximately $25–45 per person for American comfort food and craft beverages; arriving before the main dinner rush usually makes parking and seating easier. Afterward, you can take a final stroll around the square, but this is otherwise a nicely complete day—dunes, ecology, wetlands, and a small-town downtown without packing in another long drive.