Unique Engagement Photos For Massachusetts Couples

When couples reach out about engagement photos, one of the first things they tell me is that they’ve never had professional photos taken before. And that's okay! If that's you too, you're definitely not alone.

Because of that, a lot of couples initially just want “pretty.” A beautiful location, good light, photos that feel romantic and polished. And there is absolutely nothing wrong with that. An engagement session is often about getting comfortable, seeing how natural photos can actually feel, and building confidence before the wedding day.

But if you’re open to it, I'll help you create more unique engagement photos that truly reflect who you are together. To help plan your session, I’ll usually nudge the conversation a little further and ask: what do you two actually love doing together? Or, what memories are the most special to you?

In my experience, engagement sessions feel the most meaningful when they’re based in something real—a meaningful first date spot, an activity you both love, or even a little tradition you've built into your everyday life.

Sometimes that means walking to your favorite coffee shop and then wandering the Esplanade. Or sometimes, it’s reading the paper at your kitchen table before playing with your dogs. To anyone else, those moments might feel ordinary, but I see them as part of your story.

"What If We Just Want Classic Engagement Photos?"

I’ll be honest, a lot of couples tell me they mostly want the quintessential engagement session experience. They want to get used to being photographed and walk away with images that feel timeless and beautiful. That’s completely valid, and I love those sessions too.

But I also love to help my couples think about whether there’s something they do together that they never have photos of. Engagement sessions are one of the only times in your life when this season gets intentionally documented. It can be special to weave in even a small piece of your real life.

It doesn’t have to take over the entire session. Sometimes it’s just one stop, one activity, or one meaningful location to add your personal experiences into your gallery.

Some Of My Favorite Unique Engagement Photos

Some of the most memorable engagement sessions I’ve photographed in Massachusetts were meaningful not because they were elaborate, but because they were specific.

One couple chose to take their photos near Fenway Park because that’s where their relationship began. We walked around, laughed about their early dating memories, and captured photos in a place that actually held history for them.

Erin and Sean fell in love while working in the library at UMass Amherst. Instead of defaulting to a scenic overlook or a stroll through the city streets, we leaned into the place where their relationship started.

Annie and Kofi travel often by train in Worcester and love stopping at Bocado, so we incorporated both. Their entire session was relaxed and fun because it was something they genuinely do together.

Jenna and Anderson love riding the rentable blue bikes in Boston, so we let them bike!

Meghan and Tony love reading and visiting new coffee shops, so we built their session around that.

None of these ideas were over-the-top. They just reflected who the couple already was. And by choosing a setting that feels natural, the photos also feel natural. Because couples feel at home, not out of place.

Motion Creates Emotion

When you’re walking, biking, grabbing a drink, or exploring, you’re less focused on the fact that someone is taking your picture and you're more focused on soaking up the experience with the person next to you.

Starting with movement helps ease nerves, especially for couples who have never been professionally photographed before. It gives you something to do with your hands. It shifts your attention back to each other instead of the camera. And that’s usually when the most authentic moments start to happen.

How To Choose Your Perfect Engagement Session Spot

Instead of asking, “What are the best engagement photo locations in Massachusetts?” I think a better question is: what location makes sense for you?

Because what feels meaningful really depends on the couple.

That’s why I don’t usually start by handing couples a list of trendy spots. I start with getting to know them.

And If you’re trying to figure out what engagement session location would feel right, start by asking yourselves a few simple questions:

• Where was your first date?

• Where did you have your first kiss?

• Where were you when you realized you were in love?

• Is there a place you go all the time without even thinking about it—your favorite coffee shop, walking route, bar, or neighborhood spot?

• What do your best, most “you” days look like? Are you dressed up and out in the city? Or in sneakers grabbing coffee? Are you surrounded by people, or is it usually just the two of you?

• When you picture your photos, do they feel calm and cozy… or busy and full of movement?

You don’t need the most impressive location in Massachusetts. You just need one that makes sense for your story. If it feels like you, it works.

One Last Thought

If you’re still not sure what location makes sense, that’s completely normal. Most couples don’t have it figured out right away.

That’s why we talk through it together.

Sometimes it takes one question or one memory to spark the idea. Other times, we land on a classic Massachusetts backdrop and keep it simple. There’s no wrong answer—the goal is just to choose something that feels comfortable and true to your relationship.

Engagement sessions shouldn’t feel like a performance. They should feel like time carved out for the two of you. And when we start there, the rest tends to take care of itself.

If you’re planning your engagement session and want help choosing a spot that fits, get in touch—I’m always happy to help you think it through!