Boston is such an incredible place to take engagement photos, with its blend of nature, iconic views, and historic landmarks! This guide features 7 of my favorite locations for Boston engagement sessions (and proposals), as well as outfit tips, activity ideas, & more. I can’t wait to show you just how many beautiful spots this city has to offer!

 


Boston Engagement Session 101


First let’s cover the basics of taking engagement photos in Boston, plus a few of the key logistics you’ll need to know.

 

Do we need to get a permit for our Boston engagement session?


It depends where we’re shooting. Certain locations around the city, such as the Public Library, may require you to get a photo permit and/or pay a fee in advance, while others are totally free to shoot at. This is something I can help you look into when we plan your session!

What should we wear for our Boston engagement photoshoot?


Oooh I love helping my couples with their outfits!! As a photographer and design aficionado, I clearly have a passion for beautiful people, places, and things, and making sure you look & feel incredible during your session.


When you’re picking outfits for your Boston engagement session, here are a few key tips to keep in mind:

  • Wearing what you feel BEST in should always be your top priority. This isn’t the time to be trying new dresses or trying to wear an outfit that’s too tight because you think it’ll “look good” on camera… find something in your closet that makes you feel confident and comfortable!
  • Neutral colors are always a safe bet, and so is sticking to the color scheme of your wedding. Avoid super bright, fluorescent colors or complex patterns that might reflect weirdly onto your skin, and look weird in the final photo!
  • Pick two looks: one that’s a little more casual, like a button-down or nice top with pants, and one that’s a bit dressier, such as a dress, elevated jumpsuit, or a cute skirt. This creates great variety in your final gallery and gives you the chance to show off multiple aspects of your personality & style.


If you are doing two separate outfits, let me know ahead of time so I can bring my pop-up changing tent so we don't need to stress about finding a restaurant, hotel or somewhere for you to change. Getting this tent has been such a life saver and is so perfect for these kind of sessions!

I have a LOT more tips when it comes to styling your engagement session, so I compiled them all into another guide for you to read next!


When is the best time of day to take engagement photos in Boston?


One of my biggest Boston engagement session tips is to shoot in the early morning, especially if we are shooting on a weekend! Sunrise gives you soft, glowing light and peaceful, almost cinematic moments without distractions. I also recommend shooting on weeknights for a golden hour glow for beautiful photos as well.


When is the best time of year to take engagement photos in Boston?


I actually think that Boston is amazing for engagement photos all year round! The city has SO many amazing spots to choose from, both indoor and outdoor—you could have a gorgeous session at the Public Garden in the summertime, or a romantic & cozy session inside of the Public Library in the winter.

And don’t worry: no matter what time of year we shoot, I am always checking the weather app leading up to our session so we can prepare to make the best of any scenario!


All in all, when you have your session is really up to you & when your wedding date is. As well as when you’d like to send out your invites (if you’re planning to include your engagement photos in your design).

Want to find out where you should & shouldn’t include your engagement photos in your wedding stationery? 👀Check out my guide to How to Design Your Dream Wedding Stationery!


Is Boston a good place to propose?


YES!! Boston is an amazing place to propose to your partner, with so many stunning views of the city skyline, picturesque parks, and quaint little city streets. Whatever your vibe is, you can find a dreamy spot to pop the question—and turn the rest of the day into a celebratory date around the city! Every location I’ve included in this guide is amazing for BOTH engagement photos and proposals, so keep on reading :)


P.S. Be sure to read my blog post about How to Plan the Perfect Proposal for planning tips, logistical advice, & more! Including how to get your partner to the proposal spot… without giving it away.

 

Best Locations for Boston Engagement Photos & Proposals

 

 

Whether you’re imagining your engagement session in a lush garden, along brick-lined streets, or in front of a historic brownstone (or all of the above?!), Boston has just the place you’re looking for. There are sooo many amazing spots around the city to explore, but here are 7 of the best Boston engagement session locations to get you started!

 

1. Boston Common

Of course the Boston Common has to be number one on this list—it’s only the most popular park in the city! Fun fact about Boston Common, it’s actually the oldest city park in the country at over 350 years old, so there’s plenty of history to be found here. It’s a great starting spot for your engagement session, and then we can head to the Public Gardens + end in the streets of Beacon Hill.

2. Public Garden

The Public Garden is easily my favorite photo spot in Boston! Located in the heart of the city next to Boston Common, it’s such an enchanting botanical garden with winding pathways, rich greenery, and vibrant flowers. Here you’ve got the iconic bridge, pretty willow trees, a large pond with Swan Boats, and beautifully-designed monuments & fountains everywhere. It’s a no-brainer place to stop when you’re visiting all the Boston hotspots!


When shooting at the Public Garden, I like to either do it in the early morning around 9-10am, when there aren’t a ton of people out yet, or golden hour. The lighting just before sunset is absolutely stunning, and is worth it even if I have to edit out some crowds in the back of the photos!


Because I live an hour outside of Boston by the CT border, I usually end up parking at the Boston Common Garage, and find it best to meet up with my couples at the entrance to the Public Garden, by the bridge. This gives us plenty of space to meander around and have fun before running off to Beacon Hill!


3. Beacon Hill

This neighborhood is one of the top Boston photography locations, and is absolutely perfect for a Boston engagement at any time of year. There are amazing locations all around the area and it’s full of charming alleyways, historic brownstones, and cobblestone paths. One of the best parts about taking photos here is that you get the blend of nature in Boston Common first, then the iconic historic city look of Beacon Hill, within just a few blocks! You get a truly incredible variety without needing to drive or taking the T to change locations.


I have a few favorite spots in the Beacon Hill area that I typically gravitate toward, but I also try to do something different for each session—whether that’s going down a street I’ve never been down before, or shooting on a different corner… something to make your session interesting and unique to you!


I am slightly biased toward September-November sessions here, because Beacon Hill in the fall is pure magic… just look at Alex and Ben’s session to see what I mean. The decorated stoops, the brick-lined streets, and the leaves scattered across the sidewalks in the autumn months truly make every corner look like a movie scene.

4. Christopher Columbus Waterfront Park

If you want to be closer to the water for your Boston engagement session, Christopher Columbus Waterfront Park is an amazing option. This park connects a spacious area of greenery to the waterfront harbor in the north end of Boston, with beautiful paved walkways, a large lawn, and an iconic archway covered in wisteria vines. With water on one side and the city skyline on the other, the views from this park are literally beautiful everywhere you look, especially on a sunny day!

5. Long Wharf

Not far from Christopher Columbus Waterfront Park is the Long Wharf, Boston’s historic pier where you can watch all kinds of sightseeing boats and ferries pass by. You get to enjoy gorgeous scenery of the harbor, and there’s a hotel & multiple shops/restaurants you can check out in the plaza. The wharf is an easy walk from the park if you want to shoot at both locations, and we can always stop by the outside of the New England Aquarium to see some seals too!

6. Fan Pier Park

A popular spot particularly for proposals is the Fan Pier Park, which provides a great view of the wharf and Boston skyline—making it the perfect backdrop for your proposal. Though it’s amazing for engagement photos as well!


The first time I shot a proposal here, I actually saw 3 different proposals happen before my couple’s proposal. So keep in mind that it can get really crowded on summer weekends, but it’s still really pretty and fun! For a bit more quiet and privacy, you might want to opt for a weekday and/or a non-summer date, instead.

7. Boston Public Library

By now, you can probably tell that there are so many cool locations to shoot at in Boston—but one in particular that I’ve been dying to go to is the public library! The interiors are enchanting as heck, with stunning chandeliers, striking artwork, and overall DREAMY 19th-century architecture. The only thing is that their fees for photography sessions are crazy expensive, so the cost may or may not be worth it to you! ($750) We can always stay outside of the library and still shoot in front of the stunning building exteriors & stroll through the streets around it.  


Fun Ideas for Your Boston Engagement Session


If you know me at all, then you know I like to tell all of my couples to embrace their session and turn it into a full-on date! You’re already dressed up and looking fabulous, so why not, right? Nobody ever said no to a romantic night in the city after taking adorable photos together ;)


There are SO many ways you can make your Boston engagement session (or proposal) more fun and personalized, especially in the Beacon Hill/Boston Common area. A few ideas I love:

  • Grab a slice of pizza from Sal’s
  • Run over to the Charles River Esplanades
  • Sip a cup of coffee at Tatte or Blank Street
  • Bring a prop that feels personal to you (like your favorite book, game, drink, etc.)
  • Stop in a local bookstore or shop that fits your vibe/hobbies/personalities
  • Grab drinks at a nearby bar or hotel
  • Bring a blanket & set up a lil’ picnic in the park
  • Pop into a local store and pick up a bottle of celebratory champagne

And don’t be afraid to think outside of the box here. One of my favorite engagement sessions of all time was this magical gondola session in Downtown Providence! Just shows you how we can get creative together & brainstorm super unique ideas like this!


How to Book Your Boston Engagement Photo Session


Are you ready to plan your own Boston engagement session or proposal?!


Whether you’re feeling pulled to Boston’s iconic gardens, scenic harbor views, or the hidden alleyways of our historic neighborhoods, I’ll be there to capture every second. Reach out and tell me allll about what you’re picturing—I’m dying to know which of these locations are calling to you most!


Don’t miss my full Engagement Session Planning Guide next, where I give you even more deets about what to expect before, during, & after your session!