When William Penn carefully planned out Philadelphia in the 1680s, he envisioned a “Green Country Town” with a neat grid of streets connecting five evenly spaced public squares. Today, that grid has expanded, its streets turning many unexpected corners, and the city is bigger and busier than Penn could have imagined. The original five squares – known today as Rittenhouse, Logan, Washington, Franklin, and Penn – are far from the agrarian open spaces they once were. Like so many American cities, Philadelphia has known growth and decline and renewal, turmoil and violence and progress, tradition and change. Although it is often passed over as a destination in favor of cities like Boston, New York, and Washington, D.C., it is as fascinating and beautiful as any city in the country. 

But to me, what stands out most about Philadelphia is the degree to which it retains a feel of the past. There are bits of New York like this, and bits of Boston, but they are bits, scattered here and there. In Philadelphia, they are whole neighborhoods, streets that lead to other streets, hidden little worlds where you almost think you might get lost. In this major American city, full of grand historic sites and memories of pivotal moments, home to significant cultural institutions and acclaimed restaurants and other flashes of newness, it is these quiet blocks that always command my attention.

I’ve been to Philadelphia several times, and there are many areas I haven’t even begun to explore. (They’re on my list though!) This is a large city, after all; it sprawls across about 141 square miles, and has a population of roughly 1.5 million people. (For comparison, Manhattan is 22.8 square miles (pop. ~1.6 million), and Hartford is just about 18 square miles (pop. ~123,000.) Plus, there’s so much packed into the area known as Center City, which is easily accessible from the train station, that it’s easy to spend all your time in these central, walkable neighborhoods. On a recent visit, I wanted to see more of the city’s squares, and especially to wander its narrow streets and even narrower alleys, warrens of cobblestoned lanes where modern life almost slips away and every detail seems to have been designed to be photographed. 

This is by no means a comprehensive guide to Philadelphia, or even to all of its prettiest streets. But if you love preserved historic buildings and urban neighborhoods, tree-lined alleyways, and lovely little details, here are some perfect places to start your wandering.

Fitler Square 

This quiet neighborhood on the Schuylkill River is the kind of area that’s all too easy to picture yourself living in. Its eponymous park – bordered by Pine, Panama, 23rd, and 24th Streets – is not one of Philadelphia’s original squares, but it is a peaceful spot to pause for a minute on your walk. The area is largely residential, and many of its streets consist of block after block of dreamy historic buildings, adorned, like those in other parts of the city, with colorful doors and shutters. The cutest of all are the slim streets and alleys where it’s hard to imagine any vehicle larger than a small-ish SUV squeezing by. Some picturesque examples are Panama Street between 24th and 25th Streets, South Croskey Street between Lomabrd and Pine Streets, and South Van Pelt Street between Spruce and Locust Streets. As you walk down Philadelphia’s narrowest roads, look out for the even tinier alleys that sprout off from them, tempting you to follow to a dead end or a cobblestone maze.

Rittenhouse Square

An upscale neighborhood known for its luxury dwellings and high-end shopping and dining, Rittenhouse Square is not without its humble – and highly photogenic – little side streets.  You get a sense of this on South Rittenhouse Square; follow this road to 17th street where it feels considerably calmer and older than the other sides of the square, with their tall buildings and chain stores. Then head down 17th to Addison Street, and follow that, and/or similarly sweet Waverly Street, which runs parallel to it, as they jog slightly between blocks and seem to sneak through the neighborhood, leading you to one adorable spot after another. You might end up on South Smedley Street, for example, which runs between Spruce and Pine Streets, and feels, as many Philadelphia blocks do, like a tiny brick-lined secret.

Washington Square West

Philadelphia’s tourism marketing agency describes Washington Square as a blend of three neighborhoods: Midtown Village, the Gayborhood, and Washington Square. There’s a lot to see and do in this lively area, and even if you’re just hunting for photo-worthy streets, this part of town can keep you busy for quite a while. The rounded corner of the park where South Washington Square and West Washington Square meet near 7th Street gives a hint of the beauty to come. Walk to South Jessup and Irving Streets, an impossibly cute intersection that branches off in all directions, then follow along to Latimer Street, Quince Street, or wherever you feel pulled to go. South Iseminger between Panama and Cypress Streets is another must-see, as is Bradford Alley off 7th Street. Clinton Street between 10th and 11th Streets is a lovely little road, and, as you might have surmised by now, pretty much anywhere you turn in Washington Square West will reward you with a charming view.

Old City 

Old City, between the Delaware River and Independence National Historical Park, is home to Elfreth’s Alley, touted as “our nation’s oldest residential street.” It’s by far Philadelphia’s best-known alley, and much like Boston’s Acorn Street, it’s deservedly photographed often. But as adorable as Elfreth’s is, I personally suspect that its fame derives primarily from the fact that most visitors simply don’t realize there are dozens of equally squeal-inducing historic alleys throughout Center City. Still, this block is absolutely worth visiting. (Bonus if you go now: there won’t be any other tourists in the winter!) It’s really just as delightful as it looks on Instagram. And it’s not the only street you should explore in this neighborhood. Wander from Front Street up Church Street, or around North Bread Street, Quarry Street, and Race Street. These narrow streets are more commercial, and their alleyways grittier – more practical shortcuts than preserved prettiness – and even their names evoke a time long past.

Society Hill 

Society Hill is in some ways as fancy as its name suggests; still, there are modest little streets to be found amid the grand buildings that line the streets of this beautiful neighborhood south of Old CIty. The area spreads out around Headhouse Square, a collection of stately brick structures making up a historic marketplace at 2nd Street between Pine and Lombard Streets. From the square, which is surrounded by small shops and restaurants, stroll through the pretty residential blocks to tiny Stamper Street, all bricks and trees with a wee garden oasis. Or walk past the dignified old homes on Delancey Street to American Street, another alleyway where brightly painted doors and hanging flags beckon. From here, you’ll probably want to continue, from one block to the next, and explore this enchanting neighborhood. No matter which way you turn, you can’t go wrong.

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An Amtrak ride to Philadelphia’s 30th Street Station takes four hours from New London or three hours from Bridgeport. Philadelphia’s subway system, SEPTA, is easy to navigate, but all the neighborhoods mentioned above are simple and pleasant to walk to from the station and from one another. For example, it’s about a one-hour walk from 30th Street Station to Elfreth’s Alley, and a ten-minute walk from Fitler Square to Rittenhouse Square. All the locations in this post could be seen in one full day, or, if you prefer to stop more often and walk at a more leisurely pace, spread out over two or three days.