Eleanor St.

Make left and walk one block to Cobden St., where you’ll want to take a peek down this steep section of Eleanor. Each fall, Pittsburgh cycling enthusiasts host a 50-mile bike race that goes up 13 of the city’s steepest hills. Eleanor St. is one of the Dirty Dozen. Cyclists start this leg at Josephine St., at the base of the Slopes, and race up Holt and Eleanor to finish at Cobden St.