Hit the Trail Challenge & Walk N Roll 2026

This is it! May begins one week from today when all trail users start logging their miles in support of our amazing local trail system. May is the month - Hit the Trail! Miles can be logged using an online form, joining our Strava Club, or by submitting a log sheet in person or email. And remember that your in-town trips reduced count for Connect Whitefish’s Walk N Roll Initiative, a City program designed to encourage human-powered transportation: walking, biking, and rolling around Whitefish. The City initiative promotes reduced vehicle traffic and fosters safer streets and healthier habits.
Prizes will be awarded throughout the month thanks to local businesses!
HTTC awards donated from Glacier Cyclery, REI, Oboz, onX, and Haskill Creek Farms. Walk N Roll awards donated from Rockfish, Third Street Market, Markus Community Market, Glacier Cyclery, The Wave, Imagination Station, and a City Beach Gazebo Rental!
Rally your WORKPLACE Team!
By joining HTTC as a workplace team, you and your coworkers will support our goal of raising $30,000 for the Whitefish Trail this spring, directly contributing to trail maintenance, improvements, and year-round access. It’s a fun & active way to build team camaraderie while giving back to the Whitefish Trail. For-profit companies can register a team for $200, nonprofits and current sponsors participate for free. Get your coworkers together, hit the trail, and make an impact! The winning team receives the Sheldon the Turtle Workplace Team TROPHY to proudly display for the following year!




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This is such a great initiative for May! I love that they're making it easy to log miles whether you're a Strava user or prefer the old-school paper route. Speaking of tracking things, I was just messing around with some photos for a trail update post and ended up using a tool to make them look like low quality images on purpose just for laughs — funny how you can go the opposite direction of the crisp trail photos everyone usually posts. Anyway, really hoping the community hits that $30k goal; the Whitefish Trail is worth every penny.
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