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!

Engagement Photos at the Spanish Steps in Washington, DC

The Spanish Steps in Washington D.C. are not to be confused with the famous Spanish Steps in Rome, Italy. The Spanish Steps in D.C. are a popular landmark located in the Kalorama neighborhood, just off Massachusetts Avenue NW. These steps are actually a staircase that connects Decatur Place NW and S Street NW.

While not as famous as the Spanish Steps in Rome, the Spanish Steps in D.C. still attract visitors and locals alike who appreciate their historical significance and the picturesque surroundings. They are often used as a backdrop for photoshoots and are a peaceful spot for residents to sit and relax. Check out this recent engagement session at the Spanish Steps in DC!

Learn more about scheduling engagement photos in Washington. DC 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 12 years in Washington, DC, Richmond, Baltimore, Philadelphia and surrounding areas!

Philadelphia Race Street Pier Surprise Proposal

Race Street Pier is a popular spot for a surprise proposal or engagement photos in Philadelphia! The pier has Delaware River waterfront views and views of the Ben Franklin Bridge along with park area! Consider walk to end of Race Street Pier for a great view when you propose in Philadelphia! Scroll below to view more photos from this surprise proposal!

Top surprise proposal locations in Philadelphia

3 reasons why you should hire a proposal photographer

5 tips for planning a surprise proposal

Learn more about planning a surprise proposal in Philly by using the contact form or emailing jonflemingphotography@gmail.com

Surprise Proposal Photography includes detailed planning & advice, photography session to capture the proposal moment, portraits afterwards, and your online gallery of your beautifully processed high-resolution images delivered in 3 days. The online gallery is easy to share with friends and family! 

Cira Green Surprise Proposal

Cira Green is a privately-owned, publicly-accessible park open year-round. It is located at 80 S 30th Street, directly atop Cira Centre South Garage. Cira Green is open 7 days a week from 6:00 a.m. – 10:00 p.m. May 1 through September 30, and 7:00 a.m. – 8:00 p.m. October 1 through April 30. All hours of operation are subject to weather and rental events. Consider Cira Green in Philadelphia as a great location with a city view for your surprise proposal plans! Checkout some photos of the view:

Top surprise proposal locations in Philadelphia

3 reasons why you should hire a proposal photographer

5 tips for planning a surprise proposal

Learn more about planning a surprise proposal in Philly by using the contact form or emailing jonflemingphotography@gmail.com

Surprise Proposal Photography includes detailed planning & advice, photography session to capture the proposal moment, portraits afterwards, and your online gallery of your beautifully processed high-resolution images delivered in 3 days. The online gallery is easy to share with friends and family! 

Washington DC National Gallery of Art Engagement Photos

The National Gallery of Art one of DC’s many free art galleries and museums! They are open daily from 10am-5pm. Admission is always free! The National Gallery of Art is a world-renowned art museum located in Washington, D.C. It is comprised of two buildings: the West Building and the East Building. The West Building, designed by architect John Russell Pope, opened in 1941 and houses a collection of European paintings and sculptures from the Middle Ages to the 1800s, including works by masters such as Leonardo da Vinci, Raphael, and Rembrandt. The East Building, designed by architect I.M. Pei, opened in 1978 and focuses on modern and contemporary art, with works by artists such as Pablo Picasso, Henri Matisse, and Jackson Pollock.

The museum is renowned for its extensive collection, diverse exhibitions, and educational programs for visitors of all ages. The National Gallery of Art is an important cultural institution, attracting millions of visitors each year, and has become a must-visit destination for art lovers and visitors to Washington, D.C.

I highly recommend the Gallery of Art as one of DC’s best indoor engagement session locations!

Learn more about planning a surprise proposal or engagement session in Washington. DC using the contact form or emailing jonflemingphotography@gmail.com

National Gallery of Art Surprise Proposal

The National Gallery of Art one of DC’s many free art galleries and museums! They are open daily from 10am-5pm. Admission is always free! The Gallery of Art makes for a great indoor location for surprise proposal engagement photos to avoid bad weather or during the winter. The National Gallery of Art has two buildings: one building has modern art and the other building has classical paintings.

Learn more about planning a surprise proposal in Washington. DC using the contact form or emailing jonflemingphotography@gmail.com

Surprise Proposal Photography includes detailed planning & advice, photography session to capture the proposal moment, portraits afterwards, and your online gallery of your beautifully processed high-resolution images delivered in 3 days. Highlight images delivered within 24 hours. The online gallery is easy to share with friends and family! 

We also offer pre-designed and custom setups to make your moment extra special! 

Philadelphia Addison Street Surprise Proposal

Addison Street is a small residential street located in the Rittenhouse Square neighborhood of Philadelphia, Pennsylvania. It is a one-way street that runs for two blocks from S 20th Street to S 22nd Street, and it is intersected by Spruce Street and Locust Street. The street is lined with historic row houses, many of which were built in the late 19th and early 20th centuries, and it is known for its charming, tree-lined character. It is within walking distance of Rittenhouse Square Park, a popular gathering place in the city. The trees stay strewn in white lights all year long. Addison Street makes for a cute location for a surprise proposal in Philly! Checkout some photos from this recent surprise proposal:

Learn more about planning a surprise proposal in Philly by using the contact form or emailing jonflemingphotography@gmail.com

Surprise Proposal Photography includes detailed planning & advice, photography session to capture the proposal moment, portraits afterwards, and your online gallery of your beautifully processed high-resolution images delivered in 3 days. The online gallery is easy to share with friends and family! 

We also offer pre-designed and custom setups to make your moment extra special!