Always love seeing this adorable family! I photographed their engagement photos and wedding photos in 2017 and it’s so fun to see them every year! We met at the Wayside Inn Grist Mill in Sudbury, a spot I haven’t been to in years (and then ended up there three separate times this Fall!) and I […]

Such a fun Fall family session in Lexington! Love this adorable family! Caroline Winn is a Boston family photographer specializing in maternity, newborn, and family photography. She serves the greater Boston area (including Lexington, Arlington, Winchester, Melrose, Concord, Lincoln and more) and Cape Cod in the summertime. If you love these photos, and you are […]

I love holding family mini sessions at Wingaersheek Beach in Gloucester once a year in September! It’s seriously one of my favorite things I do all year. It was so fun to reconnect with past clients and have a little fun in the sand! This September, we got an unseasonably warm day and the beach […]

This was my second time photographing this adorable family and these two remind me SO much of my daughters! We ran around, spun in circles, gave tickles and hugs, and more! Such a fun summertime session in Sudbury! Caroline Winn is a Boston family photographer specializing in maternity, newborn, and family photography. She serves the […]

Julian was the smiliest kiddo during our session in July- I just love when that happens! Making my job easy : ) Caroline Winn is a Boston family photographer specializing in maternity, newborn, and family photography. She serves the greater Boston area (including Lexington, Arlington, Winchester, Melrose, Concord, Lincoln and more) and Cape Cod in […]

My hope for 2025 is more sessions like this one! More just kids being kids and having fun! I am now booking Summer 2025 Cape Cod family sessions in the months of June, July, August and early September. If you love these photos, and you are looking for a Cape Cod family photographer, please get […]

Sometimes the best location for family photos isn’t some fancy park, field or attraction, sometimes the best spot is your very own neighborhood! I loved exploring this little area of Brookline, which was new to me despite having lived there for 5 years in my 20s. The flowers and beautifully manicured streets were showing off […]

Don’t sleep on Spring photos in Boston! If timed right, the blooms are so pretty in the city and make for the perfect backdrop for engagement photos, family photos, maternity photos, etc.! It was so nice to catch up with this adorable family, who wanted some classic Boston photos before moving out of state! I […]

This was my first year offering Christmas themed photo sessions in my studio in Lexington! I wanted to stick with a very minimal backdrop this year and opted for a flocked tree and a simple bench. I held mini sessions over the course of two separate days in November and they went so well! I […]

A nice little mix of everything in today’s post! That’s one of the things I love about capturing families: there are so many different stages to photograph, each one so different from the next. Pregnancy announcements, maternity photos, families with little littles, families with bigger littles 😉 I held mini sessions in early November at […]