Surprise Proposal at the 18th Century Gardens in Philly

Old City in Philadelphia has a lot of beatiful locations for surprise proposals! Here is a proposal we photographed at the 18th Century Gardens in Philly! The Gardens are beatiful with a lot of greenery and the gazebo!

Here are some other popular locations to plan a surprise proposal in Philly 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 A Surprise Proposal 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!