A Weekender Guide to Philadelphia

Written by | Travel

History, culture, and special events have long enticed New Yorkers, and those visiting the Big Apple, to flock to Philadelphia for weekend trips. The “City of Brotherly Love” is only about an hour and a half away by train, and the perfect place for the culture seeker, sports enthusiast, history buff, or foodie, to explore and indulge. You may not be able to ring the Liberty Bell, of course, but you can see it up close and personally enjoy an authentic Philly cheesesteak while soaking up as much art and history as your heart desires. If you’ve never been, and looking to plan your first excursion, look no further than our Weekender Guide to Philadelphia.

Take a half day on Friday and catch an early Amtrak from NYC into Philadelphia’s opulent 30th Street Station. Twirl around and look up to its impressive coffered ceiling and regal chandeliers. Don’t miss Walker Hancock’s Pennsylvania Railroad War Memorial, a powerful sculpture of archangel Michael rising up from the main waiting area. The Instagrammable bas-relief, The Spirit of Transportation, is in the North Waiting Room. This piece, created by Karl Bitter in 1895, depicts the progress of transportation and will command your attention before you begin your first day in Philly. Hop an Uber to your hotel to set your bags down before starting out on your adventure.

There are plenty of options to enjoy “suite dreams” in Philadelphia. For the ultimate luxury experience, Four Seasons Philadelphia boasts a scenic infinity pool in the clouds and fine dining by Michelin-starred Chef Jean-Georges Vongerichten at Jean-Georges Philadelphia (try the six-course tasting menu) and local James Beard Award winner Chef Greg Vernick at Vernick Fish, a modern day oyster bar and seafood restaurant where fans rave about the branzino. Nearby, The Logan Philadelphia, Curio Collection by Hilton, offers comfortable accommodations and sweeping views of Logan Square that are so perfect you might just be tempted to order room service and enjoy the view before going out to explore. Urban Farmer, located just downstairs, is a bustling and fun place to grab a bite and a pint at this modern steakhouse. Close to Rittenhouse Square and the “Gayborhood,” Kimpton Hotel Palomar Philadelphia, an IHG Hotel, is an Art Deco style hotel right in the middle of everything. There are dozens of great restaurants close to the Palomar, but Square 1682, located just off the lobby, is an ideal place for a high quality bite (a must-try is their duck wing appetizer). The restaurant is a “tip of the hat” to Pennsylvania’s founding father, William Penn, who created the nearby Rittenhouse Square. If there’s a foodie in your group, Michael Solomonov’s mouthwatering fast-casual Dizengoff Restaurant is literally just around the corner from the hotel. Hummus, anyone?

After checking in and indulging in lunch, go out and take in a bit of everything Philly has to offer. Rittenhouse Square, both the park and surrounding neighborhood is an absolute must, where you can saunter through the tree-lined park and take in the stunning landscape around you. On any given day you’ll encounter affluent gay couples walking their perfectly manicured dogs,  musicians from the Curtis Institute of Music giving an impromptu outdoor performance, intriguing public art, a year-round farmer’s market, and more. There, just off the square, is The Rittenhouse Hotel, another sublime option for accommodations. Their Rittenhouse Spa & Club offers one of the top spas in town. Immerse yourself in a luxury wellness retreat with an expansive menu of spa and salon options as well as an indoor saltwater pool, steam room, and even an outdoor deck for even more R&R. Parc, a spectacular French bistro, is probably the most notable restaurant on the square and you’ll catch diners sipping wine and bubbly while devouring escargots and oysters day or night.

History buffs pay attention: you’re not going to fit everything into one Philly weekend – and that’s okay. You’ll definitely want to come back. Independence Hall, a UNESCO World Heritage Site is one of the most popular attractions in town so definitely plan ahead. In 1776 the Founding Fathers gathered to sign the Declaration of Independence in this building, and it is also the site where state representatives came together to lay the groundwork for the U.S. Constitution. Advance tickets are available online through the National Park Service (www.nps.gov).

If you haven’t seen it yet, the Liberty Bell also needs to be on your list. Notable for its signature crack, the Liberty Bell bears a timeless message: “Proclaim Liberty Throughout All the Land Unto All the Inhabitants thereof,” which became a stark inspiration for abolitionists fighting to end slavery. Zahav, just around the corner, is one of the best Israeli restaurants in the area. Indulge in a little mezze and laffa while you are museum hopping and be sure to save room for their sorbet for dessert! While you’re in Old City consider exploring the informative Benjamin Franklin Museum in Franklin Court, the adorable Betsy Ross House (be sure to get a selfie with Betsy), and stroll down the picturesque Elfreth’s Alley Museum where you turn a corner and will suddenly be transported back to the 1700’s. Walk slowly and take in each of the remarkable 32 homes dating back to 1703.

Philly is rich in queer history as well and Beyond the Bell Tours (www.beyondthebelltours.com) offers a Philly Gayborhood and LGBTQ History Walking Tour daily at 3:00pm as well as private walking tours. The tours are 90 minutes and include information and insight into Kiyoshi Kuromiya, Barbara Gittings, Gloria Casarez, the nation’s longest continuously-operating LGBT-focused bookstore, and more.

Up toward the Museum Mile on the Benjamin Franklin Parkway you can catch the swank Barnes Foundation where one of the world’s finest collections of impressionist, post-impressionist, and early modernist paintings hang. Albert C. Barnes collected some of the world’s most important artwork of his time and chartered the Barnes in 1922 to teach people from all walks of life how to look at art. Explore paintings by Renoir, Cézanne, Matisse, Picasso, Modigliani, Van Gogh, and more. If you’re ready to truly immerse yourself into the Philly art scene, the epic and expansive collection of Philadelphia Museum of Art should be at the top of your list. Take a picture in front of the Rocky statue out front and then do your best Stallone impression and run up the stairs like Rocky Balboa. Back inside the museum the facilities are breathtaking and the top of the line collection includes works by contemporary Philadelphia artists, works by over 250 Black artists, Grace Kelly’s royal wedding dress, an impressive room filled with arms and armor, and paintings by renowned impressionist and post-impressionist artists like Renoir, Monet, Manet, Degas, and Cézanne. Nearby, the Rodin Museum is a stunning gallery where you can experience one of the best collections of works by Auguste Rodin. The garden out front is a perfect spot to relax and enjoy a coffee before or after consuming the works of one of the art world’s great masters. The museum’s collection features nearly 150 objects revealing rich and diverse perspectives on the extraordinary career of Rodin. Across town, Philadelphia’s Magic Gardens should not be missed. Book in advance for an immersive deep dive into the work of Isaiah Zagar, a local artist who started tiling South Street back in the 1960s and never stopped. Zagar has created over 100 mosaics in the city, with the majority of them along the South Street corridor. The Magic Gardens, which features tiles made out of cement, bicycle spokes, bottles, ceramic shards, and all kinds of knick-knacks, is inspired, creative, and completely engrossing. Be sure to charge your battery as it’s the perfect spot for TikTok or your IG story.

It’s no secret that Philly has a lively theater scene. Walnut Street Theatre, a National Historic Landmark, holds the distinction of being the oldest theater in the country. Their current season includes shows like Cat on a Hot Tin Roof and Jimmy Buffett’s Escape to Margaritaville. The sold-out buzzy production of The Cherry Orchard drew a lot of New York theater queens down to the City of Brotherly Love last year. The Wilma Theare is continually doing interesting and evocative work including the upcoming production of Guillermo Calderon’s Kiss, Nathan Alan Davis’ Eternal Life, Part 1, and a bold reimagining of Shakespeare’s Twelfth Night. The Kimmel Cultural Campus boasts the stunning Academy of Music and the Kimmel Center. On any given night you can take in live theater, music, dance and even comedy. The Academy of Music features the popular Broadway Series where locals can catch touring Broadway shows like Jagged Little Pill and Come From Away. The Kimmel Cultural Campus features several premier performing arts groups including Philadelphia Ballet, The Philly POPS, and PHILADANCO. Every summer, Shakespeare in Clark Park is the place to be for outdoor fun with the Bard. Locals flock to any performance of the indie performance group The Bearded Ladies Cabaret. The Hum’n’bards Theater Troupe is a queer musical collective that makes original productions for the Philadelphia theater and nightlife communities.

Ready for a nightcap? Philly’s Gayborhood is bustling every night of the week. Woody’s Philadelphia, a landmark destination in Philly nightlife for over 40 years, is the most popular gay bar in town. Bike Stop, the oldest leather bar is an inclusive space where you can live out your fantasy in a judgment-free zone. Voyeur Nightclub, a hip, stylish 3-floor dancehall offers late night drinks, dancing, and plenty of eye candy. If you need a late-night bite before you retire, a cheesesteak might be just what the doctor ordered. We don’t want to get into local foodie politics, but the competing giants of the city include Pat’s King of Steaks, Geno’s Steaks, Dalessandro’s Steaks & Hoagies, and Jim’s of South Street. Give them all a try and let us know which one is your favorite. Definitely have an idea if you want to have your cheesesteak “wit” (with onions) or “wit-out” (no onions) before ordering.

Before you depart Sunday afternoon, be sure to get a picture in front of the LOVE landmark, a Robert Indiana sculpture that rests in John F. Kennedy Plaza (“LOVE Park”). If you need more love in your life, head over to the nearby AMOR sculpture, the Spanish edition of the sculpture on display just over at Sister Cities Park. If you’ve enjoyed the local foodie scene, pick up something tasty to take home from one of the dozens of vendors at Reading Terminal Market. If you have a little more time, consider a visit to the old Eastern State Penitentiary where you can take in an incredible audio tour, “The Voices of Eastern State,” guided by actor Steve Buschemi and learn about Al Capone’s tenure at America’s most historic prison. Now that you’ve dipped your toe into the rich pool of everything Philly has to offer, when will you return?

The PHS Philadelphia Flower Show, the nation’s largest and world’s longest running horticultural event is in early March, Philadelphia Phillies baseball is in full swing in April, and Philly Pride will take place in June. And where better to celebrate July 4 than the place where the creation and signing of the Declaration of Independence took place almost 250 years ago? Keep an eye on the Visit Philly website (www.visitphilly.com) for more events and maybe we’ll catch you in town sometime soon!

Last modified: February 1, 2023