Cars driving on a road next to a bike path with cyclists riding along it
Greater Madison Metropolitan Planning Organization (MPO)

Smart Trips Challenge

The RoundTrip Smart Trips Challenge takes place every September 1-30.

This free, fun initiative encourages people who live and work in Dane County to swap their solo drives for biking, riding the bus, walking/rolling, and carpooling instead—and celebrates those choosing sustainable options year-round.

How to Join🏆

Anyone 18 and older can join the Smart Trips Challenge by creating a free RoundTrip account!

During the challenge, simply log your eligible trips in RoundTrip's CommuteHub platform for chances to win exciting weekly and grand prize drawings.

Register with RoundTrip

Note: We love walking & biking for fun and fitness—however, this challenge focuses on trips that save you money and reduce local air pollution by replacing a solo drive.

Smart Trips Challenge 2026 logo with icons of a pedestrian, person in a wheelchair, bus, bicyclist, person on a scooter, carpool, and vanpool.

2026 Smart Trips Challenge: September 1-30

Check back in mid-August for more details!

2025 Smart Trips Challenge

Our Collective Impact

  • 336 participants
  • 9,296 bus, bike, walk/roll, and carpool trips
  • 48,000+ miles traveled
  • $11,700+ saved on gas and car maintenance
  • 17.7 tons of CO2 emissions avoided

    —the same as taking four gas-powered cars off the road for an entire year! 

  • 1,200,000 calories burned

2025 Challenge Sponsors

Thank you to the local businesses and organizations that generously donated weekly and grand prizes for the challenge:

  • Metcalfe’s Market at Hilldale
  • TREK Bicycle Madison East
  • Machinery Row Bicycles
  • Madison Bikes
  • Metro Transit
  • Monk’s Bar & Grill – Middleton
  • Buck & Honey’s
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