Smart Trips Challenge Is Here: Try a New Way to Get Around This September | Greater Madison Metropolitan Planning Organization (MPO) | City of Madison, WI Smart Trips Challenge Is Here: Try a New Way to Get Around This September Smart Trips Challenge Is Here: Try a New Way to Get Around This September posted September 1, 2026 – 11:34am As students head back to school and fall routines begin, RoundTrip Greater Madison is challenging people across Dane County to swap trips they would normally drive alone for more affordable, sustainable options like biking, taking the bus, carpooling, and walking or rolling. The fourth annual Smart Trips Challenge runs September 1–30. It's free and open to anyone 18 or older who lives or works in Dane County. The challenge encourages people to consider different ways to get around for everyday trips—whether that means taking the bus to work, biking to meet friends, carpooling to class, or walking to run an errand. Participants can log those trips throughout September for chances to win more than 20 weekly and grand prizes. There are a few new things this year that we're really excited about. Our RoundTrip Greater Madison app is now live, making it easy for people across Dane County to log their trips and find transportation options that work for them. And for the first time, participants can create teams with friends, family, neighbors, or coworkers, so they can take on the challenge together. — Zia Brucaya, RoundTrip Program Manager Participants who log at least four round trips in a week will automatically be entered into that week's prize drawings. Those who log at least 16 round trips during September will also be entered into the grand prize drawings. Replacing drive-alone trips can help people save money on gas and parking,