Your engaged era is one of the most exciting times of your life. And your engagement photoshoot is like a little time capsule of who you two are right now. As a Boston engagement photographer, I fully believe that your engagement photos should tell your story and feel true to who you two are as a couple, full stop. One of the biggest factors of that? The location you choose for your session. It’s no secret that Boston is full of breathtaking spots, so narrowing it down to one or two can definitely be tricky, but that’s what I’m here for!

My whole goal is to make this fun and easy for you. That’s why I’ve compiled a list of my personal favorite engagement photoshoot locations in Boston that make your engagement session feel like an exhale, not a photoshoot.

A couple sitting on a bench during their engagement photoshoot, captured by a Boston engagement photographer

A couple laughing in a black and white engagement photo

A couple kissing in a hallway for their engagement photoshoot, captured by a Boston engagement photographer

A Boston Engagement Photographer’s Top 7 Spots for Your Engagement Photoshoot

Every couple is different, and that’s why I love what I do so much. Getting to tell your story through your photos is my literal dream, so I want to make sure that your engagement photoshoot actually feels true to who you are.

That’s why I’ve chosen seven different spots with seven different vibes, so that there’s a little something for everyone. All you have to do? Show up and be yourselves.

Beacon Hill: For the Romantic Couple

Cobblestone streets, antique lanterns, and historic houses make the Beacon Hill neighborhood ohhh-so charming. I’m always so obsessed with how cute the photos turn out here!

There’s always this one street I take couples down where the light hits just right and I swear I squeal every time.

If you’re going for a little bit of an antique, warm, romantic vibe for your engagement photoshoot that feels like you’re wrapped up in old-Boston coziness, Beacon Hill might just be your dream spot.

The Best Time to Take Engagement Photos at Beacon Hill

In my opinion, Beacon Hill always makes a perfect backdrop for fall and winter engagement photos with its dim, warm lighting and brown hues. Keep in mind that it’s a pretty popular area, so a weekday is always best to beat the crowds here! And since the streets are lined by houses, I like to hit the neighborhood close to sunrise or sunset to get the best lighting.

What to Wear for Your Engagement Photoshoot at Beacon Hill

Beacon Hill gives you the opportunity to dress up or dress down for your engagement photos. It just has that charm that fits the vibe no matter your style!

One of my favorite engagement photoshoot outfit ideas for a shoot here will always be neutral colors, a chic coat, and a satin dress. Shannon’s outfit? Literally the inspo of all inspo!

A couple posing for their engagement photoshoot in Beacon Hill

A couple posing on cobblestone streets for their engagement photoshoot, captured by a Boston engagement photographer

A black and white photo of a couple crossing the street at Beacon Hill, captured by a Boston Engagement photographer

A couple crossing the street in Beacon Hill, captured by a Boston engagement photographer

A couple posing for their engagement photoshoot in Boston

Jamaica Pond: For the Coastal Couple

Jamaica Pond has my heart. If you’re searching for a spot with waterfront views and a park feel, this is the one! There’s such a variety of backdrops here, which adds so much interest and storytelling to your gallery.

The Best Time to Take Engagement Photos at Jamaica Pond

Jamaica Pond shows OFF in the fall, but it’s also a great spot to catch a golden summer sunset. Note that this park does events on the weekends, so you’ll typically always want to choose a weekday shoot here!

What to Wear for Your Engagement Photoshoot at Jamaica Pond

Your wardrobe here fully depends on the season you’re taking your photos, but I’ll always love a good white and blue palette to really nail in that coastal vibe!

Leah’s outfit for their fall engagement photoshoot, complete with a satin skirt and a sweater tank, made my Boston engagement photographer heart so happy. It was the perfect effortless elegant feel for a stunning area like Jamaica Pond!

A unique engagement photo with sailboats in the background captured by a Boston engagement photographer

A couple posing for their engagement photoshoot under a sign at Jamaica Pons, captured by a Boston engagement photographer

A couple posing at Jamaica Park for their engagement photoshoot

A couple posing for coastal engagement photos in Boston

A couple holding out their hands showing off their rings, captured by a Boston engagement photographer

A couple walking along the streets at Jamaica Pond with fall-colored trees above them

The Esplanade: For the Classic Couple

If your idea of an engagement photoshoot has a variety of photo ops, including a park, a river, and city views, The Esplanade is for you. It’s perfect for a simple, traditional engagement photoshoot, making it one of my absolute faves!

The Best Time to Take Engagement Photos at The Esplanade

I’m obsessed with how The Esplanade looks in the spring. The blooming flowers and the river view just has the best energy, perfect for a spring morning!

What to Wear for Your Engagement Photoshoot at The Esplanade

Helen and Jason did it all right: a simple, yet classy, outfit for the first half of the shoot, then an outfit change into a more casual look for the second half. The Esplanade fits both of these styles so perfectly that you can’t go wrong!

We’ll do a lot of walking here, so be sure to wear something you feel good in. Like, actually good.

A man kissing his fiancee on a bridge, posed by a Boston engagement photographer

A man lifting up his fiancee on a dock, posed by a Boston engagement photographer

A couple sitting on a bench at The Esplanade for their engagement photsohoot

A couple posing on a bridge for engagement photos at the Esplanade

A couple posing with the city skyline behind them, captured by a Boston engagement photographer

A couple posing for engagement photos at the Esplanade in Boston

A couple kissing in front of blue flowers in Boston

North End: For the Couple Who Wants Some Character

North End is seriously dripping in character. So much lovely architecture, so many fun places to pop into, and the photo ops of my actual dreams! It’s the perfect location for any couples wanting something a little bit different, and a little less traditional.

As a Boston engagement photographer, I love to get some street photos here (duh!), but then I also love to pop into some bars and restaurants while we’re at it.

The Best Time to Take Engagement Photos at North End

North End is actually gorgeous year-round, and fits the vibe of any season so well. If you want to beat the crowds, a weekday morning is your best bet. But if you’re wanting to get some indoor photos here, most things open closer to noon, and I know how to work around a crowd!

What to Wear for Your Engagement Photoshoot at North End

The opportunities for outfits here are endless. Whether you’re packing a casual outfit, a classy outfit, or somewhere in between, it’ll fit in at North End!

Aubrey and Justin are giving major outfit inspo with elevated outfits that looked so good against the backdrop that I can’t even handle it.

A couple eating a meatball sub from both ends during their engagement photoshoot

A couple posing in North End Boston, captured by a Boston engagement photographer

A couple posing for their engagement photoshoot in front of a window

A couple posing on the streets of north End, captured by a Boston engagement photographer

A couple drinking espresso martinis in a cafe, taken by a Boston engagement photographer from outside of the cafe

A black and white photo of a couple having espresso martinis during their engagement photoshoot

Public Garden: For the Simple Couple

Public Garden is one of the most popular spots in Boston for a reason. It’s breathtaking, it’s perfect for an engagement photoshoot, and it’s super romantic! If you want to take your engagement photos at a place with no fuss that’s just a pretty backdrop and good vibes, that’s Public Garden.

Pro tip: Public Garden is super close to Beacon Hill, so if you want to hit both spots during your shoot, I’m always down!

The Best Time to Take Engagement Photos at Public Garden

I always tell my couples that it’s best to do your engagement photoshoot here on a weekday, because Public Garden is a popular weekend spot!

If you want that true garden feel, springtime around sunset is a moment. We’ll get gorgeous flowers and peaceful light that feels like it’s there just to frame you. I’m obsessed!

What to Wear for Your Engagement Photoshoot at Public Garden

Public Garden is perfect for that traditional engagement photoshoot outfit: a white dress paired with neutral colors, or even some pops of blue, like Colin’s shirt!

A woman sitting on her fiance's lap during engagement photos at Public Garden

A couple's photo taken by a Boston engagement photographer of them on a bridge at Public Garden

A couple posed by a Boston engagement photographer during their engagement photoshoot at Public Garden

A blurry photo taken by a Boston engagement photographer of couple looking at city from Public Garden

A couple walking through public garden for their engagement photoshoot

A couple posed by a Boston engagement photographer in Public Garden

The Boston Public Library: For the Couple Who Loves the Academia Feel

Is light academia your aesthetic? Love that for you. If so, the Boston Public Library is full of photo-op spots you’ll be obsessed with. Stunning architecture, pops of color from the art, and tons of editorial moments make this one of the engagement photoshoot locations I can’t get enough of!

Note: The Library does require a permit to take your engagement photos here, but I’ll help you with all the tricky stuff!

The Best Time to Take Engagement Photos at the Boston Public Library

The Boston Public Library took care of the hard part for us! They offer engagement sessions at 8:00 am during the week, before they open, so that we beat the crowds. Note that an engagement photoshoot here does cost $750, so be prepared for that!

What to Wear for Your Engagement Photoshoot at the Boston Public Library

Academia vibes, always. Neutral colors, a plaid coat, and a simple base? Chef’s kiss. Natalie and Adam killed it, with simple (but classy) outfits in an earthy palette that fit the Library SO well.

A couple posing for engagement photos in the Boston public library

A couple kissing on the stairs of the Boston Public Library

A photo captured of a couple through a door by a Boston engagement photographer

A couple posing for an engagment photoshoot in Boston public library

An engagement photo taken by a Bosotn engagement photographer at the Boston public library

Fan Pier Park: For the City-Loving Couple

Love city views? Same. Fan Pier Park has one of the best skyline views in Boston, so if you’re a couple that loves that feel, it might just be your best spot!

The Best Time to Take Engagement Photos at Fan Pier Park

Sunrise here on a summer day? So gorgeous. Again, I’ll recommend a morning on a weekday here for the best lighting and getting the park all to ourselves.

What to Wear for Your Engagement Photoshoot at Fan Pier Park

Personally, I love a pop of color against the colors of the skyline! Katie’s rust orange and black outfit for her surprise engagement (eek!) was spot-on, and the perfect inspiration for your own engagement photoshoot outfit!

A photo taken by a Boston engagement photographer of a surprise proposal at Fan Pier Park

A black and white photo of a couple looking at the Boston skyline

A couple sitting on the ground in front of the water at Fan Pier Park

A couple posing for their engagement photoshoot at Fan Pier PArk

A couple walking along the path at Fan Pier PArk for their engagement photoshoot

A girl showing off her engagement ring to a Boston engagement photographer

How to Choose Your Engagement Photoshoot Location

Pick the Place That Tells Your Story

At the end of the day, picking the location that feels the most like you is the key to a gallery you love. Your engagement photos should show off your personality, not hide it! I want this to feel like a little date night, not a performance. So if it feels like you, it’s perfect.

Choose Somewhere With Meaning

If you have a certain first date spot or frequent date spot, it’s always so cute to add that in as a photo location. Anything that adds intentionality, sentiment, or meaning to your photos will always melt my heart and make for the best pictures.

For example, for Shannon and Aidan’s session, we made a pit stop at their first date spot and the photos turned out so adorable. I can’t even tell you how many times I said “You look SO cute,” during this session!

A man feeding his fiancee pizza at their first date spot

A couple posing in front f a pizza restaurant, captured by a Boston engagement photographer

Think About Your Wedding Aesthetic

Chances are, you’ll be using your engagement photos for save-the-dates or invites, so consider your wedding colors in your engagement photoshoot! If you’re going for a garden party wedding vibe, Public Garden might be the best place to get your session done. If you’re going for a moody, romantic feel, the Boston Public Library might be for you!

Ask Your Photographer

As your Boston engagement photographer, I will always help you choose the place that fits you two the best. I’ll be there with you every step of the way, from choosing your location to helping you choose your outfit to all the boring logistic stuff, so all you have to do is show up and be cute!

A black and white photo of a man holding and spinning his fiancee

A man kissing his fiancee underneath a tree

A black and white image of a couple standing in front of the Boston skyline from Public Garden

Ashley Olafsson Photography | Boston Engagement Photographer

If choosing still feels overwhelming, don’t worry. I help every couple pick their locations based on their vibe, their story, and what feels the most natural.

If you’re looking for a Boston engagement photographer who will make you feel super natural in front of the camera, hype you up all day long, and maybe even become your new best friend, that’s all me! You can click here to inquire about booking me. I’m already smiling thinking about your session.

Xoxo, Ashley

My 7 Favorite Boston Spots for Your Engagement Photoshoot, From a Boston Engagement Photographer