Ride across
Illinois
October, 2025
Price - $1,199
âBeing from Chicagoland, I never knew what laid outside the big cityâ
~ C. W.
Itinerary
Thursday - Riders will meet at 5:30pm at Chicago Union Station. Bikes and gear will be loaded into transport vehicles as riders catch the 5:55pm Amtrak for Princeton IL. After a relaxing 1:45 train ride step out into one of the most beautiful small towns in the Illinois.
Friday - The day starts with a group breakfast at the local diner. Then riders start out on the brick roads of Princeton and through the historic red covered bridge. The ride heads West passing Ronald Reagans birthplace and then bound for the Mississippi River. Most of the day will be on paved country roads but will have sections on paved or limestone paths and gravel roads. The first day concludes with riding the Great River trail along the banks of the mighty Mississippi. Then kick up your feet having a burger and drink overlooking the Mississippi river as the leaves are changing colors.
Saturday - Where Friday was flat, Saturday morning is not. Starting out with a series of 200â climbs the morning rides up and down the river bluffs near the Mississippi Palisades. The ride then turns East heading across the northern edge of Illinois. Rolling out of the Mississippi river valley and into endless corn and soybean fields. The day ends descending into the Rock River Valley kicking back for another riverside meal.
Sunday - The ride navigates the Rockford suburbs (yes those exist) before returning to the lightly rolling farmland. The Rock River rollers become the Fox Valley rollers as the Chicago metropolitan area nears. Using a series of rider friendly suburban roads and trails riders will head into Chicago via the famed lakefront path.
-
Amtrak ticket
3 Nights hotel
3 Breakfasts, 2 Lunches, & 2 Dinners
Gear Transport
Stocked & Staffed Aid Stations
On Call Sag Support
-
Meet at Chicago Union Station Thursday at 5:30pm
Option for suburban bike/gear drops on Wednesday
Finish on the lakefront path heading south into the city.
-
Average high 70
Average low 50September tends to be breezy and sunny.
-
Day 1 - 95 miles, Flat
Day 2 - 95 miles, Flat to Rolling
Day 3 - 95 miles, Flat
Trip Total - 285 miles & 5kâ elevation -
We call it our escalator. Jump in the van and make the day achievable. We will bring you to aid 1 putting you ahead for the day, jump you from aid 1 to aid 2, or bring you from aid 3 to the hotel. We set you up to have the most scenic and enjoyable experience possible.
-
We recommend an all road bike.
Over the course of the 3 days riders will encounter country gravel, crushed limestone, brick pavers, country roads and paved pathways.
E-bikes with Batteries over 700Wh are welcome. We will support you on the journey but can only provide limited sag support due to the weight of the bike. -
Single Occupancy
Bike Rental
Post Ride Food & Snack Service
Bike Build & Rebox
Personal Sherpa