engagement

A Winter Engagement Session on Boston’s North Shore

February 25, 2025

A Boston couple taking winter engagement session photos at the beach

Maddie and Dillon’s winter engagement session was a vibe. I’m so excited to share their photos today! 

As a Boston wedding photographer, I’ve found that when couples are deciding whether to do engagement photos and when to take them, most people automatically think of the summer or fall. But winter sessions can be absolutely incredible too! So In this post, I’m sharing some helpful info about winter engagement photos, with some great examples from Maddie and Dillon’s session. 

A Boston couple taking winter engagement session photos on the beach

A Winter Engagement Session for Maddie + Dillon

When Maddie and Dillon first started planning for their engagement shoot, they knew right away that they wanted to take their photos on the North Shore. That’s where they met, and they love spending time in the area. It was important to them to incorporate locations that reflected their interests and their love story, and I’m so glad they did! 

We were able to hit a few locations together, including a fun bar in Salem, MA, and then Good Harbor Beach in Gloucester, where they spend lots of time together in the summer. 

I also loved their outfit ideas as well. Their looks were relaxed and cozy, and sophisticated and elevated at the same time. They fit the setting perfectly!

Winter Engagement Photo Locations

I love being a resource for my couples when it comes to planning engagement pictures. Whether you’re looking for ideas for the perfect location, or just need some general tips, I’m always here to help! 

Here are some of my favorite winter engagement photo locations: 

  • The North Shore Coast – The entire North Shore area has tons of parks, beaches, and outdoor spaces to explore. For example, for Maddie and Dillon’s shoot, we went to Glaucester’s Good Harbor Beach, and for Elli + Cam’s session, we spent time along the cliffs in Marblehead. 
  • Salem & Newburyport – I absolutely LOVE these two towns, they both have such historic charm! So many cute streets to wander down with gorgeous old homes as a backdrop. Hanna + Kevin’s engagement session in Salem is one of my all-time favorites.     
  • The North End, Boston – I do a lot of engagement shoots in the North End during the summer, (like this one!), but it is also super fun in the winter. There are lots of cozy cafes and restaurants to pop in and out of and of course great food! Who can resist a good cappuccino and cannoli??   
  • Crane Estate in IpswichCrane Estate is a 1920s historic mansion located in Ipswich, MA. It overlooks the ocean, has rolling green hills and gorgeously manicured grounds, and is the *perfect* place for engagement photos! It also makes an incredible wedding venue, so I highly recommend checking it out.  

Engagement Pictures in the Snow

Winter engagement sessions are great for so many reasons– there are fewer crowds to work around in public spaces, scheduling is often easier, and you can get some super cozy and romantic photos.  

But my favorite thing about winter engagement sessions is the ability to get some engagement pictures in the snow! Here in New England, we have so many picturesque locations for photos, and the snowfall makes your photos even more magical. I’m obsessed! 

Looking for a Boston Engagement Photographer?

Whether you’re planning engagement photos for the winter, spring, summer, or fall, I’d love to meet you! As a Boston wedding and engagement photographer, I love meeting new couples, getting to know you, and hearing all about your love story. Reach out to me through my contact form, and we’ll get started planning! 

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BEHIND THE LENS

ABOUT kelly

At home near the sea. Ever-focused on finding beauty in intimate or grand moments; found in the love stories that leave me breathless and in awe. 

Kelly  deeply values connection by being intentional in knowing her couples and their love stories. Through her organic and natural photography style, she creates timeless images that allow you to relive your moments and remember how you felt. Kelly began her professional career in 2015 and has since been delivering skillfully crafted images and an elevated experience for every couple she works with. She will help you feel natural and relaxed in front of the camera by knowing when to give guidance and when to let the moments naturally evolve, focusing on your unique and unforgettable celebration from start to finish. Based in Boston, she would love to document your authentic love throughout New England and beyond.

©Kelly Stevens Photography 2025