A 55-foot-wide limestone cave yawning straight onto the Ohio River in far-southern Illinois, once a hideout for river pirates, with a little ferry still shuttling cars across to Kentucky.
Road trips · Illinois
Illinois road trips & hidden gems.
The stops worth changing a travel day for in Illinois — crowd-voted gems, events worth traveling for, and the public golf you can actually book. Curated by Roamward, the scenic road-trip planner.
Happening in Illinois
Lollapalooza 2026
Barely two dozen marquee events hit the whole country in a year — and Illinois has one this July. Roamward builds the trip around it: the scenic route in, the detours worth a slack day, and when rooms sell out.
Hidden gems
What locals say you shouldn’t miss.
Crowd-nominated in the Gem Hunt. Add yours and vote the finalists into the app.
Sandstone cliffs and balanced formations like Camel Rock crowning the Shawnee National Forest in southern Illinois — the quarter-mile Observation Trail has the best long views in the Midwest.
Limestone bluffs tower 250-plus feet over the Mississippi near Savanna in Illinois' hilly northwest corner, with sweeping river overlooks in driftless country that looks nothing like flat Illinois.
The Springfield diner where the battered, deep-fried hot-dog-on-a-stick was perfected, and one of the last original eateries still cooking on Route 66 — a friendly, memorabilia-stuffed stop.
A 170-foot water tower shaped like a giant 1949 catsup bottle, looming over Collinsville near the St. Louis side — pure roadside Americana with a birthday festival every July.
Tucked in the Shawnee Hills near Goreville, this rugged park hides a 100-foot intermittent waterfall at the end of Big Rocky Hollow, plus shelter caves and narrow sandstone gorges — gloriously uncrowded.
Worth traveling for
Events that put Illinois on the calendar.
Plan the Illinois trip
Get the scenic route, the stops, and the timing.
Roamward turns these into a real road trip — the drive, the detours, and the stays. Join early access for the iOS beta.