Dating back to 1703, Elfreth’s Alley is often hailed as the oldest continuously inhabited residential street in the United States. Go back in time by walking down its narrow, cobblestone lane, where Federal and Georgian-style homes still stand proudly as relics of a bygone era. At numbers 124 and 126, you’ll find a small museum offering a glimpse into the daily lives of working-class Philadelphians during the colonial era.

Dubbed the "home of American coffee culture," Portland knows what it takes to brew the perfect cup. In a 2016 survey of 100 U.S. cities, Portland topped the list, boasting the most coffee roasters per capita and the highest number of cafés. With so many spots to enjoy a great cup of coffee, you might think there's little room for discovery — but that couldn’t be further from the truth. Portland’s coffee scene continues to evolve, with unique additions like Oracle Coffee Company, run by Andy Hurley, the drummer of Fall Out Boy and a self-described "vegan straight-edge anarchist." The choices are endless, but for a glimpse of where it all began, visit the original Stumptown Coffee Roasters location at 4525 Southeast Division Street. Many credit this tiny space with launching Portland’s rise to coffee fame, now a chain with outlets from New York to LA.

At this historic Philadelphia indoor farmers' market, you can browse through a wide array of shops selling everything from fresh produce to artisanal cheeses, flowers, and handmade crafts. Be sure to indulge in lunch from one of the many diverse food stalls, featuring an eclectic mix of options like corn dogs, Middle Eastern specialties, Thai dishes, hearty burgers, and zesty Cajun cuisine.

Before you head out to explore parks further afield, take a stroll through one of Portland's most popular urban spaces: the Tom McCall Waterfront Park, overlooking the Willamette River. There's usually plenty of activity here, given all of the cyclists, skateboarders, joggers, and picnickers that come here, but even more, come to attend major outdoor events and festivals held here throughout the year. On hot summer days, many flock to the refreshing Salmon Street Springs.