Best Historic Architecture

Eastern State Penitentiary at 2027 Fairmount Avenue. From an historical perspective, the 1829 Eastern State represents early 19th century Quaker-inspired philosophy for reform (or penitence) rather than punishment and served as model for more than 300 prisons worldwide. The largest and most expensive public structure in the U.S. at the time of construction, John Haviland’s ambitious design is organized with imposing wings of cells and yards radiating from a central guard post. Designed initially for solitary confinement, the penitentiary made ingenious use of central heat, running water, and flushing toilets. Eastern State is open today as a stabilized ruin; the power of its massive masonry walls, radial plan, and grand sky-lit double-height galleries is amplified and revealed by the impact of time.

Best Restaurant

Fork at 306 Market Street. Located in Old City, Fork artfully combines a handsome loft space with creative contemporary food and a great sense of hospitality. Owners Ellen Yin and Eli Kulp continue to evolve all aspects of this restaurant—each time you visit there is another nuance or twist that keeps the restaurant relevant. 

Best Coffee

La Colombe has several locations in town, but I recommend the newest at 6th and Market Streets in the former Rohm and Haas Building designed by Pietro Belluschi. The 1964 building incorporates translucent, corrugated sunscreens made of the company’s leading product, Plexiglas. La Colombe is situated on the ground floor, a wonderful spot to contemplate the tapered columns and faceted ceilings of the concrete structure supporting the office floors above.

Best Philly Food

Everyone here has a personal “best” (and “worst”) when it comes to cheesesteaks and hoagies. My vote is for John’s Roast Pork at 14 E. Snyder Avenue. Signature roast pork with sharp provolone is worth the Uber ride to get there, as are cheesesteaks and chicken cheesesteaks. You’ll know you’re there when you see a concrete-block shed between a railway siding and strip center parking lot.

Vegans can head to HipCityVeg at 127 S. 18th Street. Carry your lunch to Rittenhouse Square a few steps away.

Best Gelato

Capogiro, Sansom Street at 13th and at 20th Streets. Capogiro is as close to gelato in Italy as I have found in the U.S.

Best Hotels

Loews Hotel at 12th and Market Streets. Housed in the landmark International style PSFS Building, designed by George Howe and William Lescaze in the late 1920s, it is worth stopping by even if you don’t stay overnight. It was surely a bold move for the conservative Philadelphia Savings Fund Society to seek a headquarters departing so completely from the neoclassic. And it is clear expenses were not spared in realizing the vision, evidenced by exquisite materials and detailing throughout the interior, much of which remains intact. Be sure not to miss the former banking hall (now ballroom) on the 2nd floor and the bank’s boardrooms (now meeting rooms) on the 33rd.