Maddie and Tim’s engagement session in South Boston was the sweetest start to our fall calendar. While fall *technically* doesn’t start until this weekend, I consider it to begin with Labor Day each year. I think Boston agreed because we had the slightest bit of golden foliage for Maddie and Tim’s portraits, especially at Castle Island! The evening had a slight chill in the air too, which was perfect for their comfy and classic second outfits.

We started their session in a familiar-to-us location in the heart of South Boston. Within moments, it felt like we’d all known each other for years! My call with Maddie earlier this year is unforgettable because we spent so much time connecting on a personal level, beyond wedding details. I was hopeful that the connection we shared would extend to Tim and Dillon, and it absolutely did!

We spent some time among the brownstones, where it felt like Maddie and Tim knew the whole neighborhood. Multiple times, friends of theirs passed by on their way home from work and cheered these two on. It made the world feel like a smaller place in the best way 🙂

As the sun began to set, we made our way to Castle Island for some portraits by the water. The light was so pretty and golden and made for such a sweet variety in their gallery! I hope you enjoy this peek into the evening we shared and the impeccable style of these two 🙂

To Maddie & Tim:

We just love you two! Thank you for inviting us to South Boston and sharing such a sweet evening with us. I could have talked with you both all night and hope we can take you up on your offer to grab dinner sometime soon! You’re both kind as can be and we’re so excited to meet your loved ones as we celebrate you at The Starting Gate next June. It will be so special to share an anniversary weekend, too 🙂

View more engagement sessions HERE!