The rolling green hills just outside of Pittsburgh’s city limits are ideal for bicycling: you’ve got cool vistas but also challenging roads. The Great Allegheny Passage is a whopping 150-mile-long trail stretching between Cumberland, Md., and Pittsburgh (don’t worry - you don’t have to bike all of it). From Steel City’s South Side, hop onto the route and travel south about 15 miles to McKeesport, where you’ll turn around for a handy 30-mile loop.
If 30 miles feels too ambitious, stop at the historic Pump House, five or so miles north of McKeesport, where you’ll find bike-friendly perks (bike racks, vending machines, restrooms and picnic tables). Stop, refuel, rehydrate and enjoy the scenery before getting back on the road again (heading back to the South Side or continue on to McKeesport for a longer ride).