Illinois: Itineraries

NOTE: Click on the titles of these suggested itineraries to open a .PDF file of each. Those printable itineraries include maps, directions, lodging, attractions, events, and more for each of the following itineraries.

Southwestern Indiana/Southeastern Illinois


Starting in Evansville, this 102-mile trip will take you along the southwest border of Indiana into Illinois. Begin your trip by exploring historical sites and museums in Evansville, then take State Route 66 to Shawneetown. Continue the trip on State Route 11 to Equality. Along the way, stop and explore Mount Vernon and New Harmony. At Equality, take State Route 1 to Rosiclare. Then take State Route 146 to your final destination in Golconda, Illinois. In Golconda, there’s something for everyone, including events and activities throughout the year. 


Southern Illinois


Starting in Golconda, this 108-mile trip will take you along the southernmost border of Illinois to Cairo. Begin your trip by exploring locks and dams as well as historical structures, then take State Route 146 to Brookport. Continue the trip on State Route 45 to New Grand Chain. Along the way, stop and see all that Massac County has to offer, from state parks to Superman! In New Grand Chain, take State Route 37 to your final stops in Pulaski and Alexander Counties. There you’ll find nationally recognized sites such as a wildlife refuge and historic districts as well as the confluence of the Ohio and Mississippi Rivers.