Sure, Philadelphia is home to icons like the Liberty Bell and Eagles football, but did you know this historic city is full of picturesque colonial backstreets, kaleidoscopic art murals and a killer food scene that’s giving its not-so-far-away neighbor New York City a run for its money? Philadelphia has all the charm of a small town with the culturally vibrancy of a big city. From the quiet benches in Rittenhouse Square to the buzzing coffee shops in Old City, Philadelphia is brimming with creativity right now.

philadelphia, city hall

Photo courtesy of Compass and Twine

We’ve got you covered on all the best things to do, restaurants to try and places to stay for your perfect long weekend in Philadelphia.

RELATED: All the Best Things to Do Along New York’s City’s High Line

Where to Wander

Elfreth's Alley, Philadelphia

Elfreth’s Alley | Photo courtesy of Compass and Twine

Go Back in Time at Elfreth’s Alley

Located in the Old City District, Elfreth’s Alley is the nation’s oldest residential street. A National Historic Landmark, it has 32 Federal and Georgian residences built between 1720 and 1830. Originally home to artisans, people still live in these houses to this day. Take your time meandering down this spectacularly preserved piece of history, admiring all the historical plaques and charming details along the way.

Rittenhouse Square, Philadelphia

Rittenhouse Square | Photo courtesy of Compass and Twine

Relax in Rittenhouse Square

In the heart of city, Rittenhouse Square was one of the original squares planned by the city’s founder, William Penn, in the late 17th century. To this day, it remains one of Philadelphia’s most iconic locations. A refuge within a metropolis, Rittenhouse Square offers bench-lined pathways and majestic, shade-giving trees. The square is surrounded primarily by luxury apartment high rises, which happen to be some of the most expensive real estate in the city. Bring lunch or a cup of coffee, find an open bench, and soak in the spirit of Philadelphia all around.

Stroll the Waterfront at Penn’s Landing

The revitalized waterfront along the Delaware River, which runs south from Ben Franklin Bridge, is known as Penn’s Landing. Named after Pennsylvania’s founder, William Penn, the area is home to multiple riverfront parks, and it often hosts entertainment events and attractions throughout the year. Check out the calendar to see what’s going on at Penn’s Landing or just go on a whim to enjoy a scenic waterfront stroll.

S. Jessup Street Philadelphia

S. Jessup Street | Photo courtesy of Compass and Twine

Get Lost in the Charming Backstreets

When you get away from the downtown city center, it’s not hard to stumble upon quiet alleyways with picturesque row houses. We fell in love with the postcard-worthy web of historic streets when we turned off of busy Locus Street and onto S. Jessup Street. It was like walking back in time. S. Jessup, Irving and S. Quince are filled with classic, colonial redbrick homes adorned with colorful front doors, matching shutters, and American flags flapping in the breeze.

What to Do

Philadelphia Museum of Art, Philly

Philadelphia Museum of Art | Photo courtesy of Compass and Twine

Run Up the Rocky Steps & Peruse the Halls of the Philadelphia Museum of Art

You just have to. Even you if you haven’t seen the movie, you know Rocky’s iconic run up of the Philadelphia Museum of Art steps. Start at the foot of the steps, admiring the Rocky Statue, then jog your way up to the top and throw your arms in the air—just like the champ. It’s a decent climb, so you probably will feel a little victorious! The panoramic view from the top, looking back at the Philadelphia skyline, is well worth effort. Don’t stop here, though: Head indoors and visit the museum. Inside, you’ll find a world-class collection of art with everything from painting from the most praised European impressionists to exceptional American art, including brilliant works from the Pennsylvania Shakers.

Old City, Philadelphia

Old City | Photo courtesy of Compass and Twine

Explore Old City

The Old City District of Philadelphia is one of the most fascinating neighborhoods in the country and our favorite place in the city. Old City buzzes with cool coffee shops and artisan-driven boutiques, which all lie peppered about the colonial-era streets, many of which are the oldest in the United States. Check out the local clothing stores and art galleries along 3rd Street, and then pop into Franklin Fountain for a root beer float or Frieda for a fresh French pastry.

Independence Hall, Philadelphia

Independence Hall | Photo courtesy of Compass and Twine

Visit Independence Hall & the Liberty Bell

In a red-brick, Georgian-style building in the summer of 1776, the Founding Fathers of the United States gathered to sign the Declaration of Independence, formally defying the King of England. Eleven years later, the U.S. Constitution was signed in the exact same building by state representatives, officially creating our nation. Today, Independence Hall remains one of the most important and well-preserved symbols of the birth of America, and it’s a must-do for anyone visiting Philadelphia. Admission is free (except for a small handling fee with advanced purchase tickets) and by tour only. Timed entry tickets are required from March–December. Directly across the street from Independence Hall, you’ll find the Liberty Bell, which once tolled the sound of freedom in Independence Hall (formerly the Pennsylvania State House). Plan to see both of these historical sites together.

Where to Eat

italian market philadelphia

Italian market | Photo courtesy of Compass and Twine

Taste Your Way Through Lunch at the South 9th Street Italian Market

The South 9th Street Italian Market is an electrifying medley of food mongers, cafés, bakeries, grocery stores, and specialty shops. Tourists head here for an afternoon of fun and food, while many locals still swing by to pick up their weekly grocery items, like cheeses and meats. Kids prance around the sidewalks eating ricotta cannoli from Anthony’s, while deliverymen zigzag around tourists with fresh produce boxes stacked to the sky on their pushcarts. Sit down at Ralph’s Italian Restaurant for a meatball sandwich, then swing by South Philly Barbacoa for a divine slow-roasted barbacoa-style taco. Obviously, come hungry!

Discover Outstanding Lebanese in Philly’s Foodie Hotspot

Without a doubt, Fishtown is the burgeoning epicenter of cultural and culinary creativity in Philadelphia. Forbes even called it “the hottest zip code in America no one’s ever heard of.” The neighborhood, located northeast of Center City and Old City, is home to some of Philadelphia’s best restaurants, including Suraya. This Lebanese restaurant and market serves up tasty Middle Eastern small plates like baba ganoush, hummous and taboulé on their all day menu. But we suggest going with friends for dinner to enjoy their great cocktails and outstanding lamb. Their Kawarma, baharat-rubbed slow roasted lamb with pomegranate-cucumber salad and dill yogurt, is one of the most flavor-filled dishes we’ve ever feasted upon.

Genos Steaks, Philadelphia

Geno’s Steaks | Photo courtesy of Compass and Twine

Take the Ultimate Cheesesteak Battle—Geno’s v. Pat’s

We would be remiss to bring up Philadelphia without mentioning cheesesteaks. On an iconic intersection in the Passyunk Square neighborhood of South Philadelphia, two of the city’s most iconic cheesesteak places happen to lie catty-corner to each other, basically staring each other down. With Geno’s Steaks on one end of the ring, and Pat’s King of Steaks on the other, you have to try them both and make the judgment call for yourself. Order “wit” or “wit-out” onions, but definitely get the cheez wiz.

Where to Stay

Lokal Hotel, Old City, Philadelphia

Lokal Hotel | Photo courtesy of Compass and Twine

Lokal Hotel

If you’re looking for a place with character in a cool part of town, look no further than Lokal Hotel in Old City (and coming soon to Fishtown). The six design-forward rooms are a far cry from your standard cookie-cutter hotel rooms. This boutique hotel-meets-Airbnb hybrid focuses on “invisible” service, with easy check-in via electronic entrance, in-room iPads preloaded with local food and delivery options, and modern amenities like Apple TV, a Sonos sound system and a fully-decked out cocktail bar. When you do leave your stylish abode, you’ll walk out the door and find yourself mere steps from all the great boutique shops and eateries in Old City.

Kimpton Hotel Monaco

The Kimpton Hotel brand’s playful, personality-filled style fits right in in downtown Philadelphia. There are a few Kimptons to choose from in the city, but our favorite is the Kimpton Hotel Monaco, just across the street from Independence Hall and the Liberty Bell. Besides its prime location, the property has chic guestrooms featuring whimsical flare and great, social common spaces. Meet up with friends for Kimpton’s signature cocktail hour during the evening in the lobby or grab a tasty brunch at the hotel’s Red Owl Tavern.

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

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