Ride across
Illinois

September 19-21, 2025

SOLD OUT

A dirt road winding through a forest with colorful autumn leaves on the trees.

“Being from Chicagoland, I never knew what laid outside the big city”
~ C. W.

Itinerary

An old, rusted metal bridge with a wooden walkway, surrounded by green trees under a clear blue sky.
A long gravel country road stretching into the distance with beside green and brown fields, a red barn and silos in the background, and a few people and horse riders walking on the road.

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 train for Princeton, Illinois. After a relaxing 1:45 train ride step out into one of the most beautiful small towns in 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 Reagan’s 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.

A dirt path running through a grassy field, leading to a wooded area in the distance. Two people walk along the path, and a small red shed is visible on the left side. The sky is partly cloudy with fluffy white clouds.
A long rural two-lane road stretching into the horizon surrounded by green fields and trees, under a partly cloudy sky.

Saturday - Where Friday was flat, Saturday morning is not. Starting out with a series of 200’ 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.

A straight, freshly paved black asphalt road runs through a rural countryside with green fields on either side, a line of trees on the left, and a clear blue sky above.
A winding dirt trail through a forest with trees in fall colors, yellow and green leaves, and fallen leaves on the ground.

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.

Map showing a route from Chicago Illinois to the western border of Minnesota with a red line marking the path across northern Illinois, southern Minnesota, and northern Iowa.

    • Amtrak ticket

    • 3 Nights hotel

    • 3 Breakfasts, 2 Lunches, & 2 Dinners

    • Gear Transport

    • Stocked & Staffed Aid Stations

    • On Call Sag Support

    • Wake up to a relaxing breakfast at or near the hotel.

    • During breakfast our staff will ensure that your device has the days course uploaded.

    • After breakfast repack your luggage and pack a day bag. Our staff will load your luggage in a van bound for the next hotel. Day bags will be loaded in a van bound for aid station #2.

    • Each morning ride will roll out in 1 single group or in waves based on terrain, ability level, and group size.

    • The 1st aid stop will be our coffee stop.  This will be between 1/3 & 1/2 way and will have coffee, sports drink, water, bananas, bars, and gels.

    • The 2nd aid stop will be our lunch stop. This will be between 2/3 & 3/4 of the way. This stop will have sandwiches and finger foods (chips/pretzels), sports drink, water, gels, bars, and your day bag.

    • Upon arrival to the hotel riders will be met with our staff who will hand out room keys and share dinner plans.

    • Dinner will be at a local restaurant or catered to hotel.

  • 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 50

    September 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 & 5k’ 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

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