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Bradley Estate Engagement Session in MA | Hailey + Dylan


Bradley Estate Engagement Session in MA

My recent engagement session with Hailey + Dylan was so much fun! I first met Hailey on a study abroad trip to Europe during my Junior year of college! She recently reached out over the summer to inquire about my wedding photography for their Castle wedding in Connecticut next year, and I was so flattered! (It’s going to be so gorgeous! I can’t wait!)  Needless to say, I was incredibly excited to shoot their Bradley Estate Engagement Session and see Hailey again after all this time! It is always so exciting to photograph and witness marriages, but especially when it’s someone you have known previously!

Eleanor Cabot Bradley Estate Engagement Session

For Hailey & Dylan’s engagement session we headed to the STUNNING Bradley Estate in Canton, MA. Hailey and Dylan were adorable together! They were both naturals in front of the camera and shared laughs and intimate, candid moments throughout the session. I loved seeing their natural laughter and interactions!  After capturing them around the building, we ventured off to explore the grounds of the venue. There was a lovely paved path lined by trees at the entrance that created the perfect backdrop. We later found another unpaved path situated in a meadow-like atmosphere.  It was the perfect secluded spot to capture the two of them and learn more about their story!   

Their Love Story 

Hailey and Dylan shared that they are both UMass graduates, but they didn’t exactly meet during college. They actually met right when Hailey graduated and was out celebrating landing her dream job. Her roommate had invited friends out to celebrate, one of which happened to be Dylan! They didn’t start dating right away, but they have now been together for over 4 years! 

The Proposal 

“The proposal was amazing in every way! 

Our absolute favorite place in the world is Nashville. We travel there several times a year and it truly is our happy place 🙂 This past year, due to the pandemic, we unfortunately had to cancel several of our planned trips to Nashville which was very difficult for us. To make up for this, we decided to plan a special anniversary trip for the first week of June to do all of our favorite activities and just be in our favorite place. On our actual anniversary (June 4th) Dylan planned the best day filled with all Hailey’s favorite things! We checked into our favorite hotel in town, spent the day sitting by the pool in a fancy cabana drinking champagne to celebrate us, and we went to dinner at our favorite steakhouse that features beautiful views of the entire city.

After dinner, Dylan suggested that we take a quick walk since it was such a nice evening. We walked all the way through town and eventually made our way to a walking bridge that runs over the Cumberland River and, again, features beautiful views of the city. While on the bridge, at one of the standing areas, Dylan decided to pause and take in the view. Then he proposed! The best part- both of our families then jumped out from their hiding places on the bridge so we could all enjoy the moment together! It was absolutely perfect! Hailey’s two requirements for this moment, when it eventually happened, was for the moment to be captured on camera and for our families to be present. Of course, Dylan pulled both of these off 🙂 The whole situation was truly the best proposal Hailey could have imagined!”

What Are Your Favorite things To Do Together?

“Anything and everything!

We absolutely love traveling together! Hailey has really gotten Dylan into Caribbean cruises and we have done this almost every year we have been together. And Dylan has gotten Hailey into EDM music festivals and we have traveled to several of these as well! We love just having the opportunity to see new places with each other and traveling together is when we have the most fun! When traveling, we love to collect fridge magnets together of the places we’ve been and our fridge is now very decorated 🙂 Our current apartment is very close to NYC and we love to go there any chance we get to explore, try new restaurants, and just do touristy things. We also love to just relax at home together and spend time with both of our families.”

What Do You Love Most About Each Other? 

Hailey: “Dylan is so intelligent and kind! He has a lot of features that inspire me and he makes me want to be a better person. He is also one of the hardest workers out there. Seeing how hard he works everyday motivates me to work harder and achieve more. He is always thinking of the little things and will do absolutely anything to make me happy.” 

Dylan:  “Hailey is the hardest worker that I know and definitely the smartest person on earth. She puts others before herself 99.99% of the time and is just the most generous person out there . . . the most honest/trustworthy person and will never ever tell a lie. She is also incredibly forgiving. Even though we argue at times, she will always forgive me and work to find the best solution for us. Hailey will always laugh at my humor and jokes even though they are not always that funny and it makes me feel loved. She is my best friend in the whole world and I’d spend 24/7 with her if I could.”

I don’t know about you, but I love learning about love stories and how couples met! It brings a smile to my face every time! After reading their answers and watching the two of them together during their Bradley Estate Engagement Session, I have no doubt that they are meant for each other! Congratulations Hailey & Dylan! I can’t wait to see you next year for your gorgeous wedding day!

More Inspiration!

For more inspiration, here are a few beautiful engagements I’ve had the honor of photographing in and around Boston MA:

Cape Cod Engagement Session at The Wequassett Resort and Golf Club

Boston Beach Engagement

Cape Cod MA Engagement Session

Massachusetts Beach Engagement

If you are recently engaged or are currently planning your wedding day, CONGRATULATIONS! I’d love to chat to see if we’re the perfect fit and how we can capture your precious memories that will last a lifetime! Contact me to get in touch, and I’m excited to hear from you!

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Boston wedding photographer

Stephanie Berenson Photography is Boston wedding photographer located in Boston, MA. Stephanie photographs weddings in Boston, Gloucester, Cape Cod, Massachusetts, Newport, Rhode Island, and all over New England. Stephanie loves to photograph classic, timeless, and elegant weddings for couples who are looking for a unique wedding experience and beautiful wedding photos.