Cliff Walk Proposal: 40 Steps

A High-Stakes 40 Steps Proposal: Navigating the Heat and the Crowds in Newport
Newport, Rhode Island, is world-renowned for its coastal elegance, but for a photographer, it presents a unique set of challenges—especially when executing a high-pressure surprise. When Brian first reached out to me regarding his surprise proposal to Kelsey, he had his heart set on the opulence of the Gilded Age. He initially considered the Marble House or The Breakers and even took a trip to inspect both mansions to ensure the fit was perfect.

However, as is often the case with event planning, life threw a few curveballs. Beyond the pandemic-era restrictions requiring masks indoors, there was a major logistical hurdle: indoor photography is strictly prohibited inside the Newport mansions. This meant that even if they were inside the grand halls of the Marble House, we wouldn’t have been able to document the actual “knee-to-the-ground” moment. Needing a location that allowed for both the grand Newport aesthetic and the freedom to photograph the event, Brian decided to pivot to “Plan B”: a 40 steps proposal on Newport’s famed Cliff Walk.

The History of the 40 Steps
The 40 Steps is a location steeped in the social history of Newport. Located at the end of Narragansett Avenue, these steps were originally constructed in the early 1800s. While the Vanderbilt and Astor families were hosting lavish galas in the mansions above, the 40 Steps became the unofficial gathering place for the Gilded Age’s “help.”

On their precious afternoons off, the Irish maids, cooks, and stable hands from the nearby estates would congregate here. It was a place of music, dancing, and community, far removed from the formal constraints of the Great Houses. While the original wooden steps were replaced with stone and concrete decades ago, the site remains one of the most popular access points to the Atlantic shore.

Why I Proceed with Caution at This Spot
Despite its history, I often tell my clients that I wouldn’t necessarily recommend this location for a surprise. A 40 steps proposal is inherently risky because it is incredibly busy, and there is absolutely no ability to control the environment. Unlike a secluded beach or a private garden, you are at the mercy of the public.

From a logistical standpoint, parking is also a major concern. My professional preference is always to select a location with guaranteed parking to ensure I am in position long before the couple arrives. Brian and I discussed these risks, and we decided to “roll the dice.” I committed to arriving at least 30 minutes early to secure a spot and scout the terrain.

The Heat of the Moment
On the day of the shoot, the Rhode Island summer was in full force. It was a scorching August day—hot, humid, and the sun was piercing. I sent Brian a text when I left my house and another when I was safely parked on Narragansett Avenue to give him peace of mind. He sent me a “sneaky” photo of Kelsey so I could recognize her outfit, and then the waiting game began.

While hiding in the sliver of shade I could find, I saw a pickup truck do a U-turn at the end of the street. I recognized Brian behind the wheel—perfect! As they walked toward the Cliff Walk, I hid my professional camera behind a stone wall, blending in as just another tourist with a backpack.

Executing the Surprise Under Pressure
Brian and I made eye contact—game on! As they began to descend the 40 steps, I followed at a distance. The challenge I feared immediately manifested: there was already a group of people at the bottom of the steps. Brian and Kelsey moved into the spot, but as they began to climb back up, Brian suddenly dropped to one knee.

Because of the crowd, I did not have a clear shot as they climbed the steps. I had to react instantly, moving down several steps and reaching over the guardrail to shoot around the tourists. Thankfully, my preparation paid off. I captured the exact moment Kelsey said “Yes!”

The Engagement Shoot: A Battle with the Elements
Following the 40 steps proposal, we transitioned into a mini-engagement shoot. The conditions were brutal. The sun created harsh shadows, and the humidity was so high I was literally dripping sweat. My shirt was soaked, and sweat was dripping from my fingers. Kelsey was dealing with similar issues.

In a moment of brilliant improvisation, I suggested they take a break to cool Kelsey off using my truck’s air conditioning. It was the perfect reset. We utilized a small patch of shade I had scouted earlier to finish the portraits. Despite the crowds, the heat, and the logistical hurdles, we produced a lovely set of images to memorialize this beautiful life moment.