Scenic 6-Pack of Iowa Towns

Madison and Warren Counties
Length: 54 miles
Surface: Paved Roads and Trails
Parking and Restrooms: Great Western Trail, Cumming

A monarch butterfly feasts on purple coneflower. Photo: Kelly Green

Beginning and ending at the Great Western Trailhead in Cumming, this hilly and scenic route passes through six Iowa communities, one winery and craft beer brewery, and the oldest covered bridge in historic Madison County. The trailhead is on the western edge of Cumming along the Great Western Trail. Head west on G4R  and pedal 21 miles through rolling hills to the T-intersection of G4R and 169. Turn south for the final 2 miles to Winterset. Caution: Hwy 169 traffic can be heavy at peak commute times.

Several charming cafes and taverns ring the Madison County Courthouse square; you can’t leave town hungry. Winterset is also the birthplace of John Wayne. Head south on P71 for approximately 1.5 miles and turn east on G50. Feast on rolling hills and scenic valleys for 11 miles until the Madison County Winery & Twisted Vine Brewery. Continue east on G50, past Hanley (three streets) for about 3 miles to St. Charles, home of the oldest covered bridge in Madison County. Walk the full length of the 81-foot-long, 1870 Imes Covered Bridge. Another 4 miles brings you to the T-intersection with R45; turn north to St. Marys. Stay on R45 to the next T-intersection with Hwy 92, turn left and ride into Martensdale. While there, make a quick stop at the Roadside Inn’s sports bar and café. Take Iowa Avenue west to the edge of town and head north on the trail for the final 9 miles back to Cumming. Be sure to visit The Cumming Tap, the local biking community’s long-time favorite small-town tavern.