Illinois road guide
The best motorcycle roads in Illinois
The best motorcycle roads in Illinois run along its edges: IL 100 under the Mississippi bluffs at Alton, the hills around Galena, the Rock River on IL 2, and the Shawnee Hills down south. Add Route 66, Lake Shore Drive and Sheridan Road for Chicago riders, and here are 13 rides worth the miles, with why each one is worth it, what to watch for and the best season.
- Roads listed
- 13
- Regions
- 4
- Best months
- May, June, Sept, Oct
- Check before you go
- Getting Around Illinois
Before you pick
How to use this list of the best motorcycle roads in Illinois
Illinois is almost 400 miles long, and the riding is at the far ends of it. The northwest corner around Galena is Driftless hill country, the Mississippi and Illinois rivers carve bluffs down the west side, and the southern tip rises into the forested Shawnee Hills before dropping to the Ohio River. The prairie in between is mostly the way to get there.
So most of these rides are weekend trips. Chicago riders can reach Galena, the Rock River and Starved Rock in a few hours, and St. Louis riders are close to IL 100 and the Shawnee. For timing, see the best time to ride in Illinois, and for the regions, the Illinois overview. IDOT's Getting Around Illinois map shows closures and construction.
Northern Illinois
Galena, the Rock River and the northern rivers
- 1. US 20 and the Stagecoach TrailWhy: The best hills in northern Illinois. US 20 rolls through the Driftless into Galena, a preserved 1800s river town, and the Stagecoach Trail winds between Galena and Lena through Scales Mound and Apple River. Watch for: The Stagecoach Trail's narrow, blind bends and tractors, and visitors filling Galena's Main Street on weekends. Best season: May to October.
- 2. IL 84, Great River Road northWhy: Follows the Mississippi through Savanna and Hanover, past the bluffs of Mississippi Palisades State Park, toward Galena. Pair it with US 20 for a loop. Watch for: Train crossings, deer in the wooded stretches and slow traffic in the river towns. Best season: May to October.
- 3. IL 2 along the Rock RiverWhy: From Rockford, IL 2 follows the Rock River south through Byron, Oregon and Grand Detour toward Dixon, past Castle Rock State Park and the giant Black Hawk statue above the river at Lowden State Park. Watch for: Weekend park traffic, deer and slow drivers in the towns. Best season: May to October.
- 4. IL 71 and Starved RockWhy: A popular day ride from Chicago. IL 71 runs along the Illinois River near Starved Rock and Matthiessen state parks, with sandstone canyons a short walk from the parking lots. Watch for: Busy park lots on weekends, and hikers crossing or walking the shoulder. Best season: May to October.
- 5. IL 29 and the Illinois River RoadWhy: North of Peoria, IL 29 follows the west bank of the Illinois River toward Chillicothe, part of the Illinois River Road scenic byway, with bluff and river views. Watch for: Truck traffic near Peoria and flooding on low stretches in spring. Best season: May to October.
Chicago and Route 66
Chicago rides and the Mother Road
- 6. DuSable Lake Shore Drive (US 41)Why: The skyline on one side and Lake Michigan on the other, the length of the city. Best at sunrise on a summer weekend, before traffic builds. Watch for: Heavy traffic, sudden lane changes, and the sharp curve at Oak Street Beach. Best season: May to September.
- 7. Sheridan Road on the North ShoreWhy: Winds north from Chicago through Evanston, Wilmette, Winnetka and Highland Park past lakefront estates, wooded ravines and the Baha'i House of Worship. Watch for: Low speed limits, strict local enforcement, cyclists and stop signs. Best season: May to October.
- 8. Historic Route 66Why: From the Begin sign in downtown Chicago, the Mother Road angles southwest past Joliet, the Gemini Giant in Wilmington, Pontiac, Atlanta and Springfield on its way to St. Louis. Murals, diners and old gas stations, and the road turned 100 in 2026. Watch for: Rough pavement on original alignments, signs that switch between old and newer routes, and I-55 traffic where the two run side by side. Best season: April to October.
Southern Illinois
The Metro East, the Shawnee Hills and the Ohio River
- 9. IL 100, Alton to GraftonWhy: The best river road in the state. IL 100 runs beside the Mississippi under tall limestone bluffs from Alton, past the Piasa Bird painting, to Grafton and on to Pere Marquette State Park. Take the free Brussels ferry across the Illinois River to extend it. Watch for: Cyclists at the bike trail crossings, weekend crowds in Grafton, and closures when the river floods. Best season: April to October, best in fall color.
- 10. IL 3, Great River Road southWhy: Heads south through the Mississippi bottomlands from the Metro East, past Chester, the home of Popeye, and on toward Cairo at the state's southern tip, with bluffs and forest rising to the east. Watch for: High water in spring, levees that hide the river, and long, empty miles between towns. Best season: April to June, September to October.
- 11. Shawnee Hills and Garden of the GodsWhy: The hilliest riding in Illinois. IL 34 leads toward Herod, and Karbers Ridge Road climbs to the Garden of the Gods, where sandstone formations look out over the Shawnee National Forest. Watch for: Loose gravel on the forest roads, deer, and fuel stops that are far apart. Best season: April to June, September to November.
- 12. Ohio River Scenic Byway, IL 146 and IL 1Why: Follows the Ohio through Golconda, Elizabethtown and Cave-In-Rock, where a free ferry crosses to Kentucky, on toward Shawneetown. Quiet river towns and bluffs. Watch for: Flooding on low stretches, ferry schedules that change with the river, and deer. Best season: April to June, September to October.
- 13. Shawnee Hills Wine TrailWhy: The backroads around Alto Pass and Cobden link a string of wineries through orchard and forest country, with the Bald Knob Cross on a hilltop above it all. Watch for: Winery traffic on weekend afternoons, tight hills, and gravel at driveways. Best season: April to June, September to October.
Summary
Illinois motorcycle roads at a glance
| Road | Region | Best season |
|---|---|---|
| US 20 and the Stagecoach Trail | Northwest | May to Oct |
| IL 84, Great River Road north | Northwest | May to Oct |
| IL 2, Rock River | North | May to Oct |
| IL 71, Starved Rock | North central | May to Oct |
| IL 29, Illinois River Road | Central | May to Oct |
| DuSable Lake Shore Drive | Chicago | May to Sep |
| Sheridan Road | North Shore | May to Oct |
| Route 66 | Chicago to St. Louis | Apr to Oct |
| IL 100, Alton to Grafton | Metro East | Apr to Oct |
| IL 3, Great River Road south | Southwest | Spring and fall |
| Garden of the Gods | Shawnee Hills | Spring and fall |
| Ohio River Scenic Byway | Southeast | Spring and fall |
| Shawnee Hills Wine Trail | Southern | Spring and fall |
Make them count
Add Illinois roads to Rippin'
Most of these roads aren't in Rippin' yet, so the first rider to add one gets their name on it. Ride it with Rippin' recording, open Segments and tap Create a Segment: drop a start gate and a finish gate and trace the line. A person on our team checks it before it goes live. Read more on segments and leaderboards and how roads get added.
A segment board is about who owns the road and who rides it, not a race. Rippin' never rewards speed on public roads.
Loops claim turf. Ride IL 84 north to Galena and come back across the hills on the Stagecoach Trail, and the land inside becomes your turf on the live map. Plan it with the loop builder. Roads riders have already added in Illinois are listed below.
Live from the app
Illinois on Rippin' right now.
7 upcoming events and 0 rider-added roads in Illinois on the map today. This list updates whenever the site is rebuilt; the app always has the latest.
- Sat Nov 7Windy City Harley-Davidson Wings & WheelsGreen Oaks
- Sun Nov 8Walneck's Motorcycle Swap Meet - Princeton - Nov 2026Princeton
- Sat Nov 28Get Stuffed at Windy City HarleyGreen Oaks
- Sun Dec 6Bikes Bears Black Sabbath Toy Run & After Party 2026Elmwood Park
- Sun Dec 6Chicagoland Toys for Tots Motorcycle Parade 2026Chicago
- Sat Dec 12Grinchmas & Toy Drive at Windy City HarleyGreen Oaks
- Sun Feb 7Walneck's Motorcycle Swap Meet - Princeton - Feb 2027Princeton
No Illinois roads are in the app yet. Add the one you love from Segments and a person on our team checks it before it goes live. How roads get added.
FAQ
Questions riders ask.
What is the best motorcycle road in Illinois?
IL 100 from Alton to Grafton is the most scenic. For hills, the Stagecoach Trail near Galena and the Shawnee Hills around Garden of the Gods are the best in the state.
Are there curvy roads in Illinois?
Yes, on the edges. The Galena area in the northwest and the Shawnee Hills in the south have real hills and curves. Central Illinois is mostly flat and straight.
What are good motorcycle rides near Chicago?
Sheridan Road on the North Shore and Lake Shore Drive at sunrise for a short ride. For a day trip, Starved Rock on IL 71, the Rock River on IL 2, or a weekend in Galena.
What are good motorcycle rides near St. Louis on the Illinois side?
IL 100 from Alton to Grafton and Pere Marquette, then IL 3 south along the river. The Shawnee Hills are a long day ride away.
Can you ride Route 66 in Illinois?
Yes. From its starting sign in downtown Chicago it heads southwest past Joliet, Pontiac and Springfield on the way to St. Louis, partly on original alignments and partly beside I-55.
Can I add these Illinois roads to Rippin'?
Yes. Any rider can add a road with Create a Segment. Someone on the Rippin' team reviews it before it goes live, and it keeps your name.
Put an Illinois road on the map.
Download Rippin' free, ride one of these with it recording, and add it as a segment. Your name stays on it.
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