Courtney & Will’s Boston engagement session was almost ruined by the rain, but it ended up being a blessing in disguise! As I approached my parking garage in Boston, I got a text from Courtney with a weather update. She said, “Rain decided to start earlier than expected.”

They were definitely a little stressed when I arrived about the rain and unsure if we should go for it or reschedule. We decided to go for it armed with clear umbrellas, Courtney and Will trusted me to roll with the punches. We had pockets of no rain and a fairly empty Boston Public Garden to make some magic happen!

Best Boston Engagement Location

The Boston Public Garden is gorgeous any time of year, but especially in the early fall as the leaves are just starting to turn. We decided to take our more formal photos in the garden, which suited their classy style. Courtney’s green monochromatic outfit with a pleated skirt looked stunning on her and perfectly complemented Will’s green dress pants. We used the bubble umbrellas as needed, but we ended up loving how the photos turned out, despite some rain!

Courtney and Will actually met in middle school and started dating in high school. There were lots of Cheesecake Factory & movie theater dates during that time! They just moved back to Boston in the Fall of 2022 from NYC for Will’s job and to be closer to their families. Will proposed in Central Park while they were on their way to brunch. He made sure it was well executed by talking to her sisters about ring styles, hiring a photographer, and even asking a stranger to film it. They would always walk their dog Maple through Central park, so it was a meaningful spot and reminiscent of their engagement photos in Boston’s Public Garden.

Beacon Hill Engagement Photos

We also walked around Beacon Hill to get some more casual shots. We found some cool doorways we used as backdrops as we walked along the brick-lined streets. They brought along their pup Maple to join in on the fun! We, unfortunately, did not get an empty Acorn Street, but I used some editing magic to fix that!

I always love the opportunity to shoot engagement photos for my couples. Courtney and Will took a few minutes to relax and settle in (like most of my couples!) so it will help them feel more prepared for their wedding day portraits. I can’t wait for their wedding at Farm Neck Golf Club in Oak Bluffs, MA!

Read more Boston Engagement Sessions at the Charlestown Navy Yard and the Boston Public Garden.