Romantic Westport MA Engagement | New England Photographer

Some sessions feel like a dream and this romantic Westport, MA engagement session was exactly that. From the moment I arrived, it was clear how in love Annee and Caleb are. Their chemistry was so effortless and genuine, I barely had to direct them. They were just themselves, completely in love and naturally photogenic. Every single photo had me literally gasping with excitement behind the camera.

Romantic Westport MA Engagement Session

We started their session at Annee’s family’s vacation home in Westport, Massachusetts. This quiet, intimate location has been part of her life since childhood, making it a meaningful setting to capture this special season of their love story. It was tucked away from the hustle and bustle of everyday life and felt like stepping into a real-life romantic movie. Truly, it was such a treat to get to photograph this amazing couple in such a beautiful setting.

We chose two distinct backdrops for this Westport MA engagement session. One was a grassy field area and the other was a serene beach setting. Both gave us the timeless, coastal vibes that Annee and Caleb are planning for their upcoming wedding. They also had a different look for each location. Annee wore a flowy white dress and Caleb a light, neutral colored outfit that tied everything together for the field setting. Before heading to the beach, Annee changed into a deep blue dress, while he changed into a white dress shirt. Their outfits looked great and complemented the settings perfectly. Honestly, they looked like models. They took such gorgeous, natural photos together.

How They Met

Annee and Caleb’s love story began just over eight years ago in North Carolina, where they were both attending college. Annee attended High Point University and Caleb at UNC. After graduation, Annee moved back home to Massachusetts while Caleb went home to Georgia. Finally in 2019, after a few years of long-distance love, Caleb moved to Boston and the rest is history.

The Proposal

In the summer of 2023, Caleb was waiting for the perfect time to propose having had a ring for months. While visiting Annee’s family’s beach house, Caleb found a perfect rocky outcropping where the river meets the Atlantic Ocean. As the sun set behind them, he led Annee down to the beach and asked her to be his wife with her family watching from a distance. It all came together in the most magical way creating the perfect moment.

Now, the couple are excitedly planning their romantic coastal wedding at the Acoaxet club here in Westport, MA. I already know it’s going to be an unforgettable celebration, and I can’t wait to photograph it!