Chestnut Hill: A Storybook Stroll Through Philly’s Cobblestoned Streets

Can’t-Miss Experiences

1. Experience the arts at local theaters and museums

Catch a live performance at The Stagecrafters Theater, an intimate century-old venue, or explore Woodmere, a 19th-century stone art museum with art by prominent Philadelphians, rotating exhibitions, and events like jazz music nights and film screenings.

Galleries like Gravers Lane Gallery, NoName Gallery and Moondance Farm Studios round out the art scene.

Woodmere   — Photo by Visit Philadelphia

2. Bask in nature at beloved green spaces

Get your flora fix at spots like:

• Morris Arboretum & Gardens, a 92-acre wonder filled with treehouses, fountains, sculptures, seasonal blooms, and over 10,000 trees and shrubs
• Pastorius Park, a dog-walker’s delight, with ponds, waterways, magnolia trees and wide-open space, and
• Wissahickon Valley Park, offering popular creekside trails like Forbidden Drive at the Bells Mill Road West Trailhead, and stunning treasures like the Statue of Teedyuscung and the Historic Thomas Mill Covered Bridge (Philly’s only covered bridge).

Pro tip: Fall foliage in these areas is iconic.

Morris Arboretum & Gardens   — Photo by Visit Philadelphia

3. Celebrate at year-round festivals

Chestnut Hill’s festivities shine in every season.

May’s Home + Garden Festival and October’s Fall for the Arts Festival fill blocks with local artists and vendors, live entertainment, and food trucks.

Plus, Stag + Doe nights bring holiday whimsy every Wednesday in December, and the Arts & Eats series shines a spotlight on the local art scene with monthly First Friday events and deals.

Home + Garden Festival   — Photo courtesy Chestnut Hill Business District

4. Have an out-of-body experience at the James Turrell Skyspace

Skyspace, in the Chestnut Hill Friends Meeting, is a permanent light installation from renowned artist James Turrell.

People of all faith backgrounds can reserve space to watch the sun set through a roof opening, while colorful lights are projected on the attraction’s ceiling.

Sunrise viewings and special events also occur year-round.

  — Photo by R. Kennedy for Visit Philadelphia

5. Take a bite out of the local food scene

Market at the Fareway is packed with food vendors peddling international cuisine, including the Chestnut Hill Brewing Company & Taproom.

Don’t miss a stop at McNally’s Tavern (home of the award-winning Schmitter sandwich), plus popular spots like Baker Street Bread Co. Cafe & Bakery, Adelinas Restaurant & Bar, Cake, Bredenbeck Bakery, CinCin Restaurant, Iron Hill Brewery & Restaurant, and Cider Belly Hard Cider.

Market at the Fareway   — Photo by S. Ramones for Visit Philadelphia

6. Find treasure along Germantown Avenue

A main neighborhood thoroughfare, the cobblestoned Germantown Avenue is filled with cute shops and picturesque charm.

Load up on gourmet foods at Evergreen Cheese; snap up trendy threads at Greene Street; or pick up quality tools at the century-old William A. Kilian Hardware Co.

Locals also love the Chestnut Hill Farmers’ Market (open every Saturday year-round), and the numerous boutiques like Occasionette, El Quetzal, Villavillekula, Hideway Music and EMBER.

  — Photo courtesy Chestnut Hill Business District

Where to Stay

Though Chestnut Hill is a mostly residential neighborhood, the gorgeous Chestnut Hill Hotel is the place to stay for visitors — with fun details like 18th-century-style decor, the 1950s Andy Warhol-inspired Post Office building, and the historic Carriage House building (featuring fireplaces and reclaimed wood).

Supreme King Room at Chestnut Hill Hotel   — Photo courtesy Chestnut Hill Hotel

Local Tips

Ready to experience the area firsthand? Here are some tips to get you started:

• Chestnut Hill is serviced by SEPTA’s Chestnut Hill West and Chestnut Hill East Regional Rail lines, plus several bus routes.
• Drivers can find metered street parking and several lots along Germantown Avenue.
• Book lovers should stop at the neighborhood’s indie bookstores, including Multiverse, a bookstore specializing in speculative fiction.
• Shop hours may vary by season. It’s always a good idea to call ahead or check store hours online before visiting.