Philly Old City Engagement Photos

Old City in Philadelphia has a lot of beatiful locations for engagement photos! For this session we did some photos walking around the streets in Old City as well as at the 18th Century Gardens! Philly has lots of great locations for surprise proposal or engagement photos!

Here are some other popular locations for engagement photos near Old City:

1. Elfreth’s Alley
   America’s oldest continuously inhabited street, dating to 1703. The narrow cobblestones and colonial houses offer a timeless, romantic charm—ideally shot in late afternoon to avoid tourists

2. Merchant’s Exchange Building / Dock Street
   A Greek-Revival landmark with elegant marble steps and a semicircular façade—a photographer favorite. Dock Street’s traffic barriers give you uninterrupted, beautiful shots

3. Race Street Pier & Cherry Street Pier
   Featuring skyline views and proximity to the Ben Franklin Bridge, Race Street Pier gives a clean, waterfront vibe. Cherry Street Pier offers an edgier industrial backdrop with beams and hanging lights

4. Front & Arch Street
   Blooming cherry blossoms in spring contrast beautifully with Old City’s brick buildings

5. North Mascher & Cuthbert Streets
   A quieter cobblestone side street with vibrant doors and window boxes—less crowded, with charming colonial character

6. 18th Century Garden
   Tucked away yet historic, this small formal garden features colonial-era plants and a gazebo—ideal for intimate portraits

7. Second Bank / Portrait Gallery
   Elegant neoclassical columns offer stately, cinematic compositions

8. Kimpton Hotel Monaco & The Bank Building
   Refined exteriors, colorful awnings, and high-end architectural vibes perfect for editorial-style shots

9. Girard Fountain Park
   A peaceful pocket park with sculptural and green accents for relaxed, natural-feeling photos

LOOKING FOR An Engagement PHOTOGRAPHER IN Philly?

Learn more about planning an engagement session in Philly by using the contact form or emailing jonflemingphotography@gmail.com

The Jon Fleming Photography team has photographed over 1,000 surprise proposals and engagement sessions over the past 10 years in Washington, DC, Richmond, Baltimore, Philadelphia and surrounding areas!