Outdoor Shopping in and Around Philadelphia

Open-air shopping destinations around Philadelphia go from country charm to preppy chic to world-class style.

Take advantage of long days, beautiful weather and some of the world’s most pedestrian-friendly neighborhoods. Explore these three outdoor shopping destinations in and near Philadelphia.


Country Charm in Chestnut Hill

By the map, Chestnut Hill is part of the city of Philadelphia, but this historic district feels more like a bucolic burg in the Connecticut countryside. On either side of a cobblestoned street are charming boutiques, antique shops, restaurants and bakeries. Top stops include renowned Chestnut Hill Cheese Shop, which has been pleasing local tastes for 51 years; Hill Company, venerable purveyor of garden and outdoor décor; newcomer Sara Campbell Ltd., offering an array of luxe yet affordable women’s clothes and accessories; and perennial favorite Robertson’s, part florist, part gift shop and part Cake, an utterly enchanting greenhouse café.

Get there: Chestnut Hill is an easy train ride from Center City Philadelphia. Hop on Septa and take the R8 Chestnut Hill West to get closest to the shopping area, which runs along Germantown Avenue.

Chestnut Hill


Preppy Chic in Suburban Square

One of America’s first outdoor shopping centers, Suburban Square has an understated glamour befitting its location on Philadelphia’s storied Main Line. Here you’ll find preppy chic favorites Lilly Pulitzer, Kate Spade, Jack & Wills and J. Crew, funky finds at Urban Outfitters and gorgeous goods at Sephora and Blue Mercury. The buzz this season: the opening of a Soul Cycle and new fashion-forward women’s boutique Delsette. On the food scene, choose from an array of restaurants with outdoor seating or join the locals at the bustling Ardmore Farmer’s Market. Assemble a picnic of locally grown offerings from over a dozen vendors, then enjoy your selections alfresco on the patio.

Get there: The “Main Line” moniker comes from the train line serving a string of upscale towns west of the city. The Ardmore stop hovers beside Suburban Square, located between Anderson and Coulter avenues.

Suburban Square


World-Class Style in Rittenhouse Square

Rittenhouse Square, the elegant 6-acre park that is the heart and namesake of this shopping district, is considered one of the finest urban public spaces in the United States. With ornate sculptures, fountains and outdoor cafes lining its perimeter, the park has a bit of a Parisian feel. Walk to Walnut Street (Rittenhouse Row) and the mood turns Madison Avenue, with outposts of internationally known brands like Stuart Weitzman, Ralph Lauren and Tiffany’s. Plus, fashionista faves Intermix, Nicole Miller and Barney’s Co-Op. A block north on Chestnut Street, Joan Shepp and Boyd’s offer couture collections you might not find in Milan while DiBruno Brothers serves up delicacies to delight the most finicky eater. 

Get there: Rittenhouse Square (the park) stretches 1.5 city blocks southwest from 18th and Walnut streets. Rittenhouse Square (the shopping district) runs roughly from Broad Street to 24th Street, Chestnut to Pine streets.

Rittenhouse Square

Doreen Creede
About the author

A regular contributor to WHERE Philadelphia on chic finds in Philly, Doreen Creede has been...