Wooster Square Engagement Session | New Haven, Connecticut

There’s something undeniably special about wandering through Wooster Square with two people who are wildly in love. After starting our session at Edgerton Park, we made our way downtown toward the brick-lined streets of Wooster Square — a neighborhood that always feels like it’s holding a quiet story on every corner. Between the historic brownstones, the pockets of greenery, and the soft light slipping through the trees, it was the perfect backdrop for a relaxed, authentic engagement session.

One of my favorite parts of the afternoon was stopping at G Café on Orange Street, a New Haven gem that’s basically made for candid photos. The two of them shared donuts and iced coffee at an outdoor table, laughing, holding hands, and savoring a moment that felt so true to who they are. These kinds of details — their names written on the cups, the half-eaten pastry, the way they leaned toward each other without being asked — are the things that make engagement photos feel alive and meaningful.

From there, we wandered through Wooster Square itself, where the neighborhood’s charm did what it always does: it let the couple simply be themselves. Whether they were running down the sidewalk, wrapped up in a quiet moment on a stoop, or tucked under flowering branches, the energy stayed light, warm, and full of joy.

If you’re planning an engagement session in New Haven, Wooster Square is one of my favorite places for its character, walkability, and the way it naturally lends itself to honest, journalistic photography. It’s a place where you don’t have to do much — just show up as yourselves — and the neighborhood does the rest.