Fall Engagement Session in ​​South End, Boston by Boston Photographer | Cindy & Michael

Cindy and Michael’s Fall engagement session was absolutely amazing!! Both Cindy and Michael are from Houston and met there but have been living in Boston for over 3 years now. Cindy loves the area so she knew she wanted to capture her engagement session here in South End with their little family including their dog Charlie, who by the way was the cutest! Although, in the beginning, he was very shy and anxious he warmed up and seemed to have some fun of his own!


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Fall Engagement Session Location

I was so happy when Cindy and Michael chose to have their Fall engagement session in South End as it is one of the most beautiful parts of Boston with its gorgeous architecture and brownstones! It’s bordered by Back Bay, Chinatown, and Roxbury and is known for its Victorian Style houses and many parks. It’s honestly the perfect location for a Fall engagement session, and it’s actually where Cindy and Michael live so it wasn’t a big trek for them!


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Engagement Session Itinerary

We started the day off at their apartment and walked over to Rutland Square where we captured plenty of laughs from Cindy and Michael, and of course, included their precious puppy Charlie in a couple of shots too! Both Cindy and Michael brought two outfits for the day which I always recommend to my couples, especially if we are shooting at multiple locations! Cindy was wearing a beautiful blue dress that popped in the photos as well as a long maxi dress from Nuuly! And Michael just brought a different pair of pants! This is completely fine if you don’t have a whole different out, just changing a few things like adding a jacket or accessories works too!


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I was so happy with the weather on this day as it was only partly cloudy, so we still had some beautiful sun as well as some cloud coverage. Shooting Fall engagement sessions in Boston can be a hit or miss with the weather but we were blessed with the best of both worlds as Fall was just starting. Fall in Boston is one of my favorite seasons as the leaves start to change color and fall on the ground, it meshes so well with the brownstone work and architecture surrounding the streets.

After walking around Rutland Square and surrounding areas we decided to stop by Cindy and Michael’s favorite dive bar in the city, Anchovies. Anchovies were near and dear to their hearts so it was so special getting to capture some photos of them here. It also had such a cozy atmosphere that fits perfectly with the fall aesthetic!


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What I loved most about capturing this momentous day for Cindy and Michael was not only the love they had for one another but how Cindy and I connected over how much she loved to explore the Boston area. Cindy has an Instagram account that’s pretty big where she loves to review and make food, as well as explore New England/Boston. Of course, being a Boston photographer I personally can’t get enough of exploring the areas either!


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“GENEVIEVE ARE YOU KIDDING ME!!!!!!! These are all incredible you are so freaking talented!!!!!!! Thank you for capturing our little fam in our fav little neighborhood so well!!” – Cindy

Looking for a Boston Photographer to shoot your engagement session or wedding? Contact me through my website. I can’t wait to hear from you!

See more of Cindy and Michael’s fall engagement session in South End, Boston below, and check out Melissa & Bryan Seaport Engagement session to see another engagement session in Boston, Massachusetts!


Engagement session, Engagement session photos, Engagement photographer, Boston engagement photographer, Boston engagement pictures, Boston Photographer, Fall engagement session, Fall engagement photo outfits, Fall engagement photos 


Engagement session, Engagement session photos, Engagement photographer, Boston engagement photographer, Boston engagement pictures, Boston Photographer, Fall engagement session, Fall engagement photo outfits, Fall engagement photos 


Engagement session, Engagement session photos, Engagement photographer, Boston engagement photographer, Boston engagement pictures, Boston Photographer, Fall engagement session, Fall engagement photo outfits, Fall engagement photos 


Engagement session, Engagement session photos, Engagement photographer, Boston engagement photographer, Boston engagement pictures, Boston Photographer, Fall engagement session, Fall engagement photo outfits, Fall engagement photos 


Engagement session, Engagement session photos, Engagement photographer, Boston engagement photographer, Boston engagement pictures, Boston Photographer, Fall engagement session, Fall engagement photo outfits, Fall engagement photos 

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