2021 Imagination Ride

Imagination Ride 2021



The Virtual IMAGINATION RIDE will raise funds for the Imagination Library book gifting program which mails free books to registered children from birth to age five in Stephenson, Jo Daviess & Carroll Counties. We currently have 2,490 children registered in the Imagination Library, and our numbers continue to grow! 

Just as there is no limit to a child's imagination, there is also no limit to how far we can grow, and we need YOU!

Ride your way!
Participants can choose the riding level that best suits them and safely ride at their convenience. Choose one of our suggested routes below, or create one of your own & ride anytime September 4, 2021 through October 3, 2021

What does it cost?
Registration is donation based - you choose what you would like to pledge towards the United Way of Northwest Illinois' Dolly Parton Imagination Library!

What does it cost?

After you fill out your registration form, please head over to the donation section below to make a pledge. All money raised during this event goes directly to funding the UWNI's Dolly Parton Imagination Library for the children registered in our local communities

Bike Giveaway

One boy & one girl who participate in this year's Imagination Ride will be entered to win a new bike! Register below!

Are you the Fastest Kid in Town?
All kids who participate in the Kids Races at the Lincoln-Douglas 5K are also entered into the drawing!
For more information, please Click Here

LD5K 2021


I Agree To The Terms & Conditions Of This Event 

I agree that bicycling is a potentially hazardous activity and that serious injuries or death can occur from accidents, negligence or carelessness. I am in good health and proper physical condition to participate in the ride. I agree that route markings and maps are provided for my convenience only and not to guarantee a safe route or trip. I voluntarily participate in this event and assume all risks associated with participating in this event, including, but not limited to, illness, injury, falls, contact with participants, effects of weather, traffic and conditions of the road, all such risks being known and appreciated by me. I will obey all laws, ordinances and regulations and will do my best to make this ride fun and safe for everyone. Having read this waiver and knowing these facts and in consideration of your accepting my registration, I, for myself and for those upon whose behalf I act, waive and release the United Way of Northwest Illinois, Inc. against any and all claims, suits, or actions of any kind whatsoever for liability, damages, or compensation. I expressly agree to release and discharge United Way of Northwest Illinois, Inc. and their staff, volunteers, and affiliates, from any and all claims or causes of action and I agree to voluntarily give up or waive any right that I otherwise have to bring a legal action against United Way of Northwest Illinois, Inc. for personal injury or property damage. If I am the parent and/or legal guardian of a minor participant, I certify that the minor is in good health, qualified and in proper physical condition to participate in the ride and I hereby release, discharge, covenant not to sue, and agree to indemnify and save and hold harmless all of the above released parties from liability, claims, demands, losses or damages on the minor's account incurred in connection with the ride or its related events and activities. I will indemnify, save and hold harmless each of the released parties from any litigation expenses, attorney fees, loss, liability, damage or cost that may occur as the result of any such claims in connection with the minor's participation in the ride and its related events and activities. I grant permission to all of the foregoing to use any photographs, motion pictures, recordings, or any other record of this event for any legitimate purpose. I agree to wear a helmet during this ride.
Choose your Riding Level
Do you need to add another rider?
Additional Riders Information

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9 + 10 =
Solve this simple math problem and enter the result. E.g. for 1+3, enter 4.

To make a donation to this year's Imagination Ride, click here

or you can TEXT Ride2021 to 41444


If you are donating to sponsor a specific rider, please make sure to enter their first & last name on the donation payment

Click here for this year's Sponsorship Form

Forms can be submitted by email to:



or mailed to:

524 W Stephenson St, Suite 101

Freeport, IL 61032


Please contact us at (815) 232-4154 if you have any questions


Beginner Route 1: Read Park to Krape Park (2.5 Miles)

Beginner Route 2: Tutty's Crossing to the Wetlands Preserve (4 Miles)

Beginner Route 3: Galena, IL (4 Miles)

Beginner Route 4: Krape Park (1.1 Miles)

Beginner Route 5: Taylor Park (1.1 Miles)


Intermediate Route 1: YMCA of Northwest Illinois (14.48 Miles)

Intermediate Route 2: Wes Block to Red Oak (13.83 Miles)

Intermediate Route 3: Wes Block to Orangeville (21.03 Miles)


Advanced Route 1: 46.53 Mile Loop - Starting in Freeport

Advanced Route 2: 25 Mile Jo Daviess County Loop

Advanced Route 3: 28.23 Mile Stockton, Willow, Massbach Loop