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Missy & Joe’s Family Portraits on the Streets of Downtown Annapolis

A family poses for portraits in Downtown Annapolis, with a clock tower in the background.

It’s always a bit of nostalgia mixed with excitement when I get to work with Joe, Missy, and their boys. We’ve been capturing moments together since their first child was just a toddler, and each session feels to me like a new chapter in a long, unfolding story. This time, our adventure took us to Downtown Annapolis, a change from our usual Washington, DC spots. The Maryland State Capitol, with its historic architecture and quaint, but also dense, urban landscapes, was a great change of pace the family portrait session this year.

Our day began at the edge of the Saint Johns College campus. It’s a spot I like for its accessibility and the variety of scenes it offers. Parking’s a breeze, and the foot traffic isn’t overwhelming. The weather was on the gloomier side that day, but I found silver linings in pockets of directional light slipping through the edges of buildings and tree canopies. It’s fascinating how light can play such a pivotal role in the mood of a photograph. I’m often inclined to postpone a session when the sky conditions are gloomy like this, especially if I’m unfamiliar with my subjects, but that’s not always an option and the years of shooting have taught me how to pull out something I like in most situations.

After a few shots on the campus, we strolled down Prince George Street, a path lined with history and character. We captured some truly expressive shots. The oldest, sitting casually and pensively against the stoop of a historic house, with the quiet confidence of a teenager discovering his maturity, juxtaposed with his younger brother’s still more youthful energy moments later in his shots.

Further down the street, a spontaneous moment unfolded. While focusing on Missy and Joe with their eldest, I prompted their younger son to leap in front of the lens. The result was a quirky candid shot that captured his personality and current role in the family. That photo found its way onto a hero spot of their holiday card — exactly the sort of self-referential humor, lacking in self-seriousness, that I like to see in a family greeting.

The day unfolded with a mix of planned and impromptu moments. We used staircases and brick walls to frame shots, creating a blend of texture and depth. A stop in front of some quaint store fronts provided a perfect setting for Missy and her younger son – their interaction in front of the camera was effortless and genuine.

Making our way onto Maryland Avenue, the capitol building loomed in the background, setting a grand stage for a family portrait. The Capitol Building grounds, despite some construction, offered its own appeal. We navigated to an old cannon display, capturing the boys’ playful, brotherly relationship around the historic artillery.

A photo of Joe with his oldest son near the construction site required a bit of photoshop magic, but the final product was definitely worth the extra effort. In a perfect world I’d like to get things just right in the camera, but these moments are always rewarding.

As we made our descent from the Capitol, I grabbed a few more shots of the whole family together. Our journey took us past the wisteria mural on Fleet Street, down Pinkney’s Street, and concluded in the front courtyard of the Naval Academy. Each location provided something unique, telling a different part of our story there in Annapolis.

We wound our way back to the college campus, marking the end of our session. As always, working with Joe, Missy, and their sons was a blend of familiarity and discovery. Their willingness to embrace both traditional and quirky styles makes each session with them uniquely enjoyable. I’m already looking forward to our next adventure, wherever that may be.