Wondering whether or not you should book an engagement photo session? Learn about their benefits and how to decide.

Maybe you’re holding hands as you explore through a bustling street. Or laughing together while the city skyline glows at sunset. Or simply sitting together in the quiet of the park. These are the moments engagement photos are really about. They’re so much more than pictures. These sessions offer a chance to slow down, celebrate your connection, and capture this chapter of your story before your wedding day arrives. They’re a time to be fully present, have fun, and help you feel more comfortable in front of the camera. In this guide, I’m sharing reason why taking engagement photos matter (and why they’re actually so much more than just photos) as well as some of my favorite session locations around for engagement photos in Boston.
Compared to your marriage, the engagement season is brief, and that’s what makes it so special. An engagement session gives you space to slow down and honor this chapter in a calm, unhurried way. It’s time set aside just for the two of you, to be fully present together and capture who you are as a couple, without the structure or pressure of a wedding day.
Engagement photos give you the freedom to choose a place that feels close to your heart during this season of your life together. Maybe it’s the neighborhood you now call home, a favorite park you explore together on weekends, or a corner of the city that holds quiet, everyday memories. For many of my Boston couples, the most meaningful locations are the ones that already feel familiar, like a coffee shop or local park.
No matter where you go, these sessions are about honoring what your life looks like right now. The images feel natural, personal, and deeply true to you, and, as an added bonus, they often blend seamlessly into things like your wedding website or save-the-dates.
An engagement session is also a wonderful way to begin building trust with your wedding photographer. It gives us time to connect, get to know each other, and create a sense of ease long before your wedding day arrives. You’ll see how I guide you, how I work with natural movement and connection, and what it feels like to be supported throughout the process. For many couples, that trust makes all the difference, especially if this is your first time being in front of the camera.
If you are looking for more guidance in this area, take a look at this guide on how I help you feel comfortable in front of the camera.



Spending time together in front of the camera before your wedding day allows everything to feel more natural when it matters most. By the time your day arrives, being photographed feels familiar, not distracting, which helps your timeline flow more smoothly and leaves more space for presence and connection. Instead of thinking about the camera, you’re better able to stay grounded in the moment which results in images that feel relaxed, honest, and genuinely you.
Engagement photos can be especially helpful when your wedding day timeline feels full. If you’re planning a larger celebration or a destination wedding with limited time for portraits, an engagement session allows for relaxed, unhurried photos without the pace of a wedding day.
They can also be a great fit if you’d love more flexibility with location or atmosphere. An engagement session gives you space to choose a setting that feels natural to you, whether that’s along the waterfront, through the city, or somewhere you already love spending time together. It’s a simple, low-pressure way to document this chapter and create images that feel easy and true to you.
Even though engagement photos can be such a meaningful experience, some couples decide to skip them, and that’s perfectly okay. Life can be full, you may already have portraits from your proposal, or you may simply want to focus on wedding day photos. Whatever your choice, the most important thing is that your photography reflects your story and feels right for you.
If you do decide to take engagement photos, Boston offers so many beautiful spaces that can make your engagement session feel truly yours. From a classic library to a quiet park or a waterfront stroll, these locations provide more than just a backdrop – they create moments of laughter, connection, and presence during this special season of your lives. Here are a few of my favorite spots!
The Boston Public Library is one of the most architecturally stunning buildings in the city! It has such a rich history and beautiful design. It’s perfect if you want a classic, sophisticated look to your engagement photos. You can even schedule a session before the library opens and enjoy the space quietly together, just like during Taylor and Brenden’s session!






Boston’s North End is full of charm and character, with its classic brick buildings, winding streets, and little corners that feel timeless. I also love taking couples to the nearby Christopher Columbus Park! The park is a true hidden gem, with sparkling water views and a lovely trellis that’s beautiful in every season. It’s a place where you can explore, share a laugh, and be fully present together.



The Boston Seaport is a favorite spot for engagement sessions, and it’s easy to see why. With striking architecture, sweeping water views, and a modern, lively vibe, it’s full of energy and personality. I especially loved exploring Fan Pier Park with Hannah and PJ! We spent the day taking in views of the water and city skyline, documenting moments that still feel so memorable.



Boston is beautiful year-round, but it truly shines in the fall when the leaves begin to change. If you’re planning a fall engagement session, you can learn more about my favorite foliage spots below!
The Most Beautiful Boston Fall Foliage Engagement Locations
Not every couple takes engagement photos, and that’s completely okay! But many couples find them meaningful because they offer a chance to slow down, connect, and celebrate this season of your lives. They’re less about checking a box and more about creating memories, practicing in front of the camera, and enjoying a relaxed, joyful experience together.
Absolutely! A location that reflects your story – whether it’s a favorite park, your first date spot, or a scenic city street – adds extra personality and warmth to your images. More importantly, it gives you a space to feel present, have fun, and connect naturally, making the photos feel authentically yours.
Engagement sessions are a gentle way to get comfortable in front of the camera, which makes your wedding day experience feel smoother and more relaxed. You’ll see how your photographer works, understand what feels natural for you as a couple, and gain confidence in front of the lens. Plus, the images you capture can be used for your wedding website, save-the-dates, or even wedding décor, adding a meaningful, personal touch throughout your celebration.
If you’re drawn to the idea, it’s often a sign that an engagement session could be a wonderful addition to your wedding journey. If you need additional help deciding whether engagement photos are right for you, talk to your photographer. Oftentimes, they can help by asking questions that will help you decide whether or not an engagement session is right for you. The goal is to make your photography experience reflect your connection, your story, and what feels most comfortable for you – whether that’s engagement photos, wedding day portraits, or both.


If you’ve been wondering why you should take engagement photos, I hope this guide helped offer some insight. Engagement photos offer a chance to slow down, enjoy each other, and document moments to treasure forever. You deserve photos that reflect your connection, and an engagement session is such a heartfelt way to celebrate this season of your lives. If you’d like to plan a session or add one to your wedding package, reach out to me below. I’d love to help you document this chapter of your story!
get in touch