Sandwiched between the Big Apple and our nation’s capital, the city of Philadelphia can sometimes be overlooked. Those who do, though, are missing out on a wonderful mix of art, culture, history, food, and drink. It has tons to offer, whether for a day trip, an overnight, or longer. It’s one of the best locations to enjoy Pennsylvania in winter with family and friends.. Of course, you shouldn’t miss some of its biggest attractions and experiences but beyond that, there is wealth to see and do.
This guide will be broken down into the various neighborhoods in and around the center city and will include the greatest hits, but also things that might not be on your radar. Of note, all are close enough in proximity to walk to each other. It’s an easily walkable town- William Penn’s original grid of numbered and tree-named streets makes it easy to navigate. If your legs need a break, the Philly Phlash is a looping bus that runs from 10 am-6 pm, with buses arriving at stops every 15 min. A day pass is just $5.
Rittenhouse Square/Midtown Village
This neighborhood is known for its anchoring park, after which it is named (note: it’s one of 5 public park squares created by Penn). Its leafy trees and benches are a great place to relax and people/pet watching. It is also flanked by many high-end, doorman-fronted apartment buildings with gorgeous facades. On Chestnut and Walnut Streets, you will find dozens of shopping options, dining, and drinking options. The Gayborhood is just a few blocks to the east. Among some favorites are:
– Dandelion- prolific restauranteur, Stephen Starr, has created a British pub-style restaurant that feels like you’re across the pond.
– Parc- another Starr hit- this one feels like a Parisian brasserie.
– The Love- the last in the Starr, Rittenhouse trifecta- is known for its cheese plates.
– DiBruno Bros.- while we’re talking cheese, this shop is legendary in the city for its cheese selection. You can also find a vast selection of Italian meats, and sweets and you can dine in or find a great take-away selection.
– Gran Caffe L’Aquila- get the gelato. You’ll be glad you did.
– McGillin’s Ale House- has been around since 1860.
– Charlie Was a Sinner- vegetarian menu and killer cocktails.
– Barbuzzo- save room for the chocolate budino.
If you feel like having a stroll, a few blocks north you will find the Mutter Museum, renowned for its medical oddities and not for the squeamish. Einstein’s brain is here in all of its preserved glory. A few blocks south will take you to the Magic Garden- a mosaic marvel that is the masterpiece of a single man, Isaiah Zagar. The Instagram-worthy pics alone are worth a visit.
Market East/City Hall
Admittedly not the most picturesque of neighborhoods, it does offer several don’t-miss sights and is easily accessible by 2 large regional rail stations. Begin at City Hall- whose architectural details rival anything in Europe. You can sign up for interior and exterior tours. Just outside is Dilworth Park, where you can find roller/ice skating rinks and in the winter, the area is transformed into a holiday market. Just across the street is the iconic LOVE statue and always worth a photo op.
Continue walking East on Market Street and you can pop into Macy’s, formerly known as the Wanamaker Building. Inside one of America’s first department stores, you will find ornate arches, columns, and a massive gold organ. During the holidays, a charming, old-school style light show draws thousands of visitors each year.
A few blocks down from Macy’s is the must-visit Reading Terminal Market for some of the best food in Philadelphia. It’s almost not crowded, but the chaos adds to the fun. In business since the late 1800s, you can find stall after stall of a diverse selection of foods, groceries, and gifts, including some of the best Amish-style pastries you’ll ever eat. Finally, end your tour of this area in vibrant Chinatown, established over 100 years ago. You can find several food tours here, as well.
Philadelphia Old City
Rightfully known for its history and national treasures, this neighborhood is also a great mix of cobblestone streets, art galleries, and dining. You’d be remiss not to take in an American History Tour of Philadelphia, which includes The Liberty Bell, Betsy Ross House, Ben Franklin’s Grave, Independence Hall, Christ Church, Elfreth’s Alley, and Poe’s House.
Two more of Penn’s original squares can be found in Old City. Washington Square Park, to the south of Independence Mall, offers shady respite under towering trees, with grassy spaces and an unknown Revolutionary War soldier memorial. Nationally acclaimed restaurant Zahav is here as well and serves Israeli cuisine. Reservations are a must, though if you go when it opens at 5, you may be able to score a seat at the bar and watch the kitchen work its magic.
To the north, you can find Franklin Square. If you have little ones, this park is a great place to entertain them. Here you will find a playground, a carousel, and a Philadelphia-themed miniature golf course. Kids of all ages will enjoy the ice cream at Franklin Fountain, still retaining its old-time parlor charms.
Penn’s Landing
When you can no longer walk to the east (because you’d end up in the Delaware River), you will find yourself at Penn’s Landing. Head to Cherry Street Pier, housed in the shell of an old pier, with the Ben Franklin Bridge looming to the left (amazing view at night). Here, you will find artist galleries tucked in revamped shipping containers. A beer garden and weekend flea markets make for a nice afternoon or evening.
As you stroll southward, during the summer and winter months, you can find another rink and seasonally-themed attractions. Continue and you will next arrive at the Seaport Museum, which houses all things maritime. If you are here between May-September, then Spruce Street Harbor Park is a must. It’s been a hit since it opened and offers food and drink stands, hammocks, river-view seating, swan boats, and kayaks. Continuing the maritime theme, you could also dine on the Moshulu- a tall ship more than a century old. If you’d rather tour than eat, you can go aboard the US Navy cruiser Olympia and Becuna submarine (though both require going up and down some tight spaces).
Art Museum/Fairmount
North of Rittenhouse and west of City Hall is a neighborhood defined by its Champs-Elysée-like parkway, replete with international flags lining the roadway. Start at Logan Square (yep, another Penn-created park). Here you can explore the Basilica of St’s Peter and Paul, the Pennsylvania Academy of Fine Arts, the Academy of Natural Sciences, and the beloved Franklin Institute. If you continue down the parkway, immerse yourself in world-class museums. The Rodin Museum houses the most pieces by the famous sculptor outside of France. The Oval and its fountains lie at the foot of the Philadelphia Museum of Art. You can pose with the Rocky statue, then run up the stairs a la the movie if you are feeling so moved.
The collections in the museum are first-rate, housing art, armor, and antiquities. Behind the museum is the Water Works, considered a marvel of water/waste engineering in its time. It serves as a nice vantage point for viewing the lights of Boathouse Row and the Schuylkill River (pronounced skoo-kill).
Meander a little farther and you’ll find yourself on Kelly Drive, which is packed with people walking, biking, and blading. Circle back to the east to end in the Fairmount neighborhood, an enclave of brownstone-style homes, with several options for dining and drinking. The big draw, however, is Eastern State Penitentiary. This former prison oozes atmosphere due to being somewhat relic in nature (it was built in the early 1800s and has been shuttered for decades). Self-guided audio tours are available and you can even see Al Capone’s cell. On Halloween, the brave can visit the very popular haunted house attraction.
Conclusion
Hopefully, you’ve got a sense of all that the Philadelphia area has to offer. Center City is the highlight of this guide, as many tourists choose to stay and start here. However, if you have more time or the ability to venture a bit farther- look into University City/Clark Park, Passyunk Ave (pronounced pash-yunk)/Italian Market, Manayunk, Chestnut Hill, Fairmount Park, and Northern Liberties/Fishtown. A great unique way to explore here is to take a Philadelphia Segway Tour. Each part of the city couldn’t be more different from the others and offer their unique vibe. Happy travels!