13 Charming Streets & Alleys in Philly

Just off 2nd Street below Quarry Street in Old City is Eflreth’s Alley, one of the nation’s oldest continuously inhabited residential streets that was previously home to artisans and tradespeople of the 18th and 19th centuries. Elfreth’s Alley Association preserves the colonial-era landmark street, including 32 rowhomes with early American architectural relics like flower boxes, shutters and bond brickwork. A small lamppost sign between houses No. 115 and No. 117 points to another walking path called Bladen’s Court with adjoining homes and a larger tree-covered backyard. Don’t leave without stopping into the Elfreth’s Alley Museum at homes No. 124 and No. 126.

Nearby: Head a couple blocks west and south to explore the more-than-two-dozen historic sites in Independence National Historical Park, including Independence Hall, the Liberty Bell, The President’s House, the Benjamin Franklin Museum, Christ Church and more.

Philadelphia is full of European architectural charm, but the 2100 block of Saint James Place in Rittenhouse Square is a rare gem. This secluded half-block known as “English Village” has Tudor-style countryside townhouses dating back to the early 20th century. There’s fairy-tale charm everywhere: Two-story cream-colored brick homes on stone walkways feature pitched shingle roofs, small front-facing balconies, arched wooden doors and flowering trees in front.

Nearby: Further west on Walnut Street is an entrance to the Schuylkill Banks, an eight-mile riverfront promenade that Philadelphians hold dear. Walking, running, skating, biking and picnicking are all popular activities along this greenway.

Named after a former University of Pennsylvania provost, Delancey Street runs east-west across Center City and is a must-see spot for aspirational home-buying. Luxurious properties range from small cottages to large three-story brownstones dating back to the American Civil War. Delancey Place (at the western end of the Rittenhouse Square neighborhood) is and remains home to some of the city’s wealthiest residents. Two 19th-century townhouses at 2008–2010 Delancey Place were the homes of the Rosenbach brothers who developed one of the largest collections of rare books in the United States, now called The Rosenbach Museum and Library.

Nearby: Between 3rd & 4th Streets is Three Bears Park, a popular family-friendly playground, and Bingham Court, a townhouse complex designed by a mid-century architect with a central garden and modern art sculptures. A few blocks north is Old Saint Joseph’s, the oldest Catholic Church in Philadelphia, founded in 1733.

Philadelphians love showing off their block, with the 1700 block of Addison Street serving as a picture-perfect example. Shiny, brightly lit trees illuminate this Rittenhouse Square side street. The neighborhood has decorated these tall, arched trees with white lights for over a decade, keeping the holiday magic going year-round. Unsurprisingly, proposals (and weddings) happen here, as it’s also one of the most Instagrammable places in Philadelphia.

Nearby: Head north to Rittenhouse Row for alfresco dining and shopping at more than 200 dining, retail and cultural establishments.

Chestnut Hill — nicknamed “Philadelphia’s Garden District” — abounds with green-conscious, dog-friendly, walkable streets. Germantown Avenue is its main drag, a lively cobblestone strip of small businesses, family-run bars and restaurants, taverns, shopping boutiques, and a year-round indoor food hall. Visit during the annual Home & Garden Festival each spring, when Germantown Avenue shows off its gorgeous public outdoor spaces, colorful flower plantings and pocket parks to fellow garden enthusiasts.

Nearby: Located in Pennsylvania’s Wissahickon Valley, Chestnut Hill offers plenty of recreational options nearby, including Wissahickon Valley Park (one of Philly’s essential outdoor spaces) and the 92-acre Morris Arboretum. Also nearby: the Woodmere Art Museum, home to a collection of 3,000 works of art by Philadelphia artists.

The tiny triangle-shaped Paolone Park between Sears Street and Medina Street feels like a South Philly oasis. The 7th Street pedestrian-only block is bookended with mosaic murals from Philadelphia’s own Isaiah Zagar that were commissioned by the neighborhood. In between, passerby can take in modest rowhomes with balconies and terraces; a community garden filled with flower beds, bird feeders and tree blossoms maintained by block residents; and a memorial park dedicated to Louis Paolone Senior, who served South Philadelphia as a committeeman for 20 years. Sit on a bench seat and marvel at this 30-year-plus community effort.

Nearby: Two blocks west is East Passyunk Avenue, South Philly’s famed dining destination. The one-mile corridor boasts award-winning bars, restaurants and shops and hosts its own popular street festivals and restaurant week each winter.

Catharine Street’s 700 block is a haven for creative inspiration. At Palumbo Park, mid-block next to the Fleisher Art Memorial, people draw, craft and sketch. Others simply stop and admire the public art surrounding them, including David Tothero’s abstract steel outdoor sculpture Bonsai and Autumn Revisited and a mural by artist David Guinn that spans two walls with scenes of a forest landscape and children playing outside. Across the street, the DaVinci Art Alliance’s backyard is a quiet public gathering space with an in-ground sculptural installation as the focal point.

Nearby: Learn about South Philly’s immigrant history by walking south on Catharine Street through the South 9th Street Italian Market, one of the oldest and largest open-air markets in America. The gritty-but-glorious destination offers dozens of street vendors, produce stands and butcher shops, along with restaurants that encompass not just Italian but also Mexican, Vietnamese, Korean and more types of cuisine.

South Fourth Street has been the city’s textile and garment district since the 1930s, when fabric businesses, tailors and garment workers set up shop here. These days, Fabric Row continues as a shopping destination for second-hand thrift stores, vintage and boutique shops, cafes, home goods, galleries, and bookstores. Check out the Fulton Street mural Harmony and The Windows of Curiosities by local Black artist and designer Conrad Booker. It depicts the former Harmony Street in a larger-than-life street grid with fluttering butterflies.

Nearby: Philly’s famous South Street, located just a few blocks north, is home to a mashup of iconic spots like Philadelphia’s Magic Gardens and Theater of the Living Arts, which both stand alongside quirky galleries, indie record stores, vintage shops, tattoo and piercing parlors, dive bars and ethnic restaurants.

Off South Street on 2nd Street between Pine Street and Lombard Street is Headhouse Square, anchored by a Georgian-style brick firehouse at the north end that’s now a community center, and the Headhouse Farmers Market, one of the oldest continuously run farmers markets in the country. During warm-weather months, surrounding restaurants like Bloomsday Cafe extend their outdoor seating under the Square. Just a few steps away is Stamper Street, a narrow tree-lined street with brick wall foliage, lush plant life and a private courtyard that nods back to its colonial-era landscaping.

Nearby: A short walk east is Penn’s Landing and the Delaware River waterfront, which has endless choose-your-own adventures, including relaxing on hammocks at the seasonal Spruce Street Harbor Park, biking up and down the Delaware River Trail, or grabbing a dinner inside the world’s oldest and largest four-masted tall ship Moshulu.

Fairmount, a neighborhood named after nearby Fairmount Park and the hill it sits on, initially attracted wealthy Philly residents and is renowned for its greenery and proximity to many city landmarks. Every tiny street is a patchwork of brownstone beauty, especially Green Street’s 2100-2400 block. Ornate three-story rowhomes perch up on higher ground with sought-after decorative details to be admired, including brick facades, wooden roofs, horse-stables-turned-garages, front lawn hedges and pink cherry blossom trees.

Nearby: Head a couple blocks and find Eastern State Penitentiary, once the most famous and expensive prison in the world that now offers self-guided tours that explore the attraction’s history. Head west to explore one of the best art museums in the world, the Philadelphia Museum of Art. Or head south for two more can’t-miss art destinations: the Rodin Museum and the Barnes Foundation.

Baltimore Avenue is a bustling corridor that runs through the heart of West Philly. At the cross-section of Woodland Avenue between 40th and 41st Streets is Woodland Terrace, a street built in the 1860s by real estate agent-turned-developer Charles Leslie with 20 two-family three-story Victorian-style homes that have come to define West Philly’s architectural design. The houses on this tree-lined block from No. 500 to No. 520 stand out with features like wrap-around porches, ornamental ironwork and wide cornices, making them larger and distinct from typical Philly rowhomes.

Nearby: Several notable Philadelphians who resided on Woodland Avenue are buried in The Woodlands Cemetery and Mansion, located at the northeast end of the historic street.

Philadelphians are a celebratory bunch, and winter holidays are especially revered. (In fact, Christmas decorations often proudly remain on some residents’ homes all year long.) See this festive attitude in real life on South 13th Street between Morris Street and Tasker Street during the Miracle on South 13th Street programming every holiday season. Each neighbor transforms their rowhome with quirky holiday decorations from colorful frosted windows to wrap-around lights to elaborate full house displays and replications of famous holiday movie scenes. While this South Philly Christmas wonderland runs for about a month, holiday lights can be seen hanging above the block any time of year.