Most people from Chicago already know of “The Hamptons of the Midwest”—the towns in Michigan are close, beautiful, and the perfect escape no matter the time of year.
However, on the other side of Lake Michigan lies Door County—an idyllic peninsula that has largely gone unnoticed by tourists from outside the region.
The towns and villages of Door County are linked by the Door County Coastal Byway, a 66-mile loop that was designated as a National Scenic Byway in 2021.
Only 4 hours from Chicago, this stunning drive offers a particular appeal in the fall when the leaves change color, making it an ideal destination for an autumn getaway—ofen referred as the “Cape Cod of the Midwest.”
Small towns to visit in Door County, Wisconsin
The best time to experience the fall colors is from late September to mid-October, with the northernmost end of the peninsula reaching its peak first and then slowly moving south.
- Egg Harbor
- Fish Creek
- Ephraim
- Sister Bay
- Ellison Bay
- Washington Island
- Baileys Harbor
- Sturgeon Bay
Festivals happening in Door County, Wisconsin this fall
- Baileys Harbor AutumnFest (September 12, 2026): This festival celebrates the fall season with seasonal food, local vendors, live music, and classic vehicles.
- Egg Harbor Pumpkin Patch Festival (October 10-11, 2026): A family-friendly event that offers pumpkins, entertainment, food, crafts, and a variety of activities suitable for all ages.
- Lighthouse Festival (October 2-4, 2026): Explore all 11 historic Door County lighthouses, as well as neighboring southern lights like the Kewaunee Pierhead Lighthouse, by land, boat, and air.
- Sister Bay Fall Fest (October 16-18, 2026): The largest fall celebration on the peninsula features live music, delicious food, children’s activities, arts and crafts, and a festive parade.
