Ready for the Ultimate road trip adventure?
This August 2025, pack your bags, charge your phone, and hit the legendary Route 66 in Illinois for a one-of-a-kind photo and travel contest that celebrates the sights, spirits, and stories of the Mother Road.
We’ve mapped out 40 incredible points-of-interest (POIs) along the 400-mile stretch between Chicago and St. Louis, and we want you to explore them!
How to Enter the Contest:
Visit 20 or more POIs during August 2025
Check in at each stop using the Overlook mobile app
Upload a photo of your visit for each location
The more stops, more photo entries:
Visit all 40 POIs – earn elite bragging rights for the photo winners (and bigger prizes)
Visit 30+ sites – level up your prize options
Visit 20+ sites – eligible for photo winner prizes at this level
Enter at overlookmaps.com/contest or use the QR code here:
This is your chance to experience Route 66 like never before – and win while you do it!
So mark your calendars, rev your engines, and get ready to check in, snap pictures, and claim your Route 66 glory!
Let the road lead you to adventure.
Sponsors include:
