Route of the Hiawatha

The most thrilling easy ride on this list is a short one: about 15 miles on the old Milwaukee Road line from East Portal to Pearson, almost all of it on a gentle 1.6 to 2 percent downhill. You pass through 10 tunnels, including the 1.66-mile St. Paul Pass Tunnel, and cross 7 sky-high trestles with views of the Bitterroot Mountains. A shuttle bus carries riders and bikes from Pearson back up to Roland, leaving only the ride back through the St. Paul Pass Tunnel to East Portal; expect a wait of around 45 minutes at the bottom. Lights are required and can be rented, and rental bikes are available at East Portal with a reservation. A ticket is needed to ride, and as of November 2026 the trail is closed for the season until next year.