Whether you’ve recently gotten engaged or you’re looking to get new photos of you and your sweetheart there are so many amazing spots in Boston for your session. I’ve put together a list of the best locations for Boston engagement photos to help you pick an incredible backdrop.

I’m always open to my couples’ ideas if they have a spot already in mind that is special to them (like where they had their first date, favorite park to hang out in, etc), but if they need recommendations I’ve got loads of ideas. I was born and raised just south of Boston so I know those neighborhoods like the back of my hand.

Some of these spots are better at various times of the day due to crowds and a few require additional fees to shoot there (but most are free and open to anyone). If you are traveling into the city, I always suggest using the apps Park Whiz or Spot Hero to get discounted parking on garages throughout Boston (cause no one needs to pay steep parking prices).

You can choose to have a traditional engagement session or a more activity based one- kayaking on the Charles River, taking your boat out of the Seaport District, ice skating on Frog Pond in the winter, rocking your flannel while apple picking, braving the rides at one of Massachusetts’s local fairs etc. What matters most to me is making my couples feel comfortable and ultimately creating beautiful photos that showcase the connection you have together. If you are interested in booking me for a Boston engagement session, you can learn all about the packages and added information here.

Boston Engagement Session Locations If You Want A Waterfront View:

  • Fan Pier Park- Seaport District
  • The Esplanade
  • Navy Yard
  • Boston Harborwalk by Long Wharf
  • Piers Park

If you want rustic Boston engagement photos:

  • Boston Public Garden and Boston Common
  • Commonwealth Ave
  • Arnold Arboretum
  • Back Bay Fens
  • Christopher Columbus Park
  • Borderland State Park (outside the city in the south shore)
  • Middlesex Fells (outside the city in Stoneham, MA)
  • Gardens at Elm Bank (outside the city in Wellesley)

Boston Engagement Session Locations If You Want the Downtown Urban Vibes:

  • Boston Seaport District
  • Faneuil Hall
  • Beacon Hill
  • Rooftop Session
  • Copley Square
  • The North End
  • Fenway Park (inside or outside by Lansdowne Street)

If you want to feel like you are in Europe without leaving the state, then definitely check out the Crane Estate in Ipswich or the Hammond Castle in Gloucester.

Other top tips to keep in mind when thinking about what season to have your session:

Cherry Blossom Season: Beacon Hill, the Esplanade, the Arnold Arboretum ( Peters Hill section) and the The Brookline Reservoir explode in beautiful pink flowers late April to early May while the lilacs bloom at the Arnold Arboretum in early May. For 2021, they had bloomed from April 10 to May 8th, but it fluctuates every year depending on weather.

Tulip Season: The tulip fiends at Wicked Tulips in Exeter RI was open from April 22nd 2021 to May 8, 2021.

Lupine Season: Lupines usually go into full bloom in mid-June in Sugar Hill New Hampshire.

Fall Foliage: Peak foliage in New England varies every year so I always monitor the Folaige Maps online. In years past Massachusetts peak ran from Sept. 30 until Oct.18th and New Hampshire foliage was great from Sept. 22-Oct.13.

Christmas Tree Farms: If you want to book your winter session at a Christmas tree like Mistletoe Tree Farm we’ll want to secure the date with them in the summer months (they schedule ahead because they fill up so quick).

Lavender Farms: The Farm at SummitWynds in Holden, MA and the Cape Cod Lavender Farm in Harwich are the perfect options!

Boston Engagement Photos with Incredible Skyline Views: Boston Seaport District’s Fan Pier Park

Couple touching foreheads in during winter engagement session in the Boston Seaport District
Couple kissing during winter engagement session in the Boston Seaport District at Fan Pier Park

Why it’s a Boston Seaport Engagement Session is awesome: Epic skyline views of Boston, opportunities for photos on the dock, and views of the ocean. Need a spot closer to East Boston? Then choose the popular Piers Park!

If you are looking for more inspiration on a Seaport District engagement session you can click here for highlights of a winter session and here for a stylish fall session.

Beacon Hill

two photos side by side of a couple sitting on the steps of a beacon hill apartment during their fall boston engagement session
beacon hill fall boston engagement session
Shot for Flytographer
fiance kissing girlfriend's forehead in front of a charming beacon hill home in boston during their engagement session
black and white photo of couple kissing on a beacon hill street during their boston engagement session

Why a Beacon Hill Engagement Session is awesome: Home to the most photographed street in the USA, Beacon Hill is one of the most charming neighborhoods in Boston. You’ve got beautiful brick apartments and cobblestone lined streets + a short walk to the Boston Public Garden & Esplanade.

If you are looking for more inspiration on a Beacon Hill engagement session you can click here for highlights of a stylish fall session.

Piers Park East Boston

Copley Square

Shot For Flytographer
Shot for Flytographer
Shot for Flytographer
Shot for Flytographer

Why a Copley Square Couples Session is awesome: Located in the heart of Back Bay you’ve got the Boston Public Library, Trinity Church, and the historic Fairmont Copley Plaza as backdrops for a more fancy shoot setting.

Best time to photograph: Sunrise since this is a tourist & local hot spot in downtown Boston

Boston Public Garden & Commonwealth Ave

couple smiling at each other during their Boston Public Garden engagement session

Why a Boston Public Garden Engagement Session is awesome: The Boston Public Garden is beautiful in any season- the flowers are in bloom during the spring & summer, the fall captures New England foliage, and the snowy months create a winter wonderland.

Best time to photograph: Sunrise since this is a tourist & local hot spot

Boston Rooftop Session

boston rooftop engagement session black and white

Why a Boston Rooftop Engagement Session is awesome: There are a few rooftops in Boston that have the most incredible skyline views featuring historic Boston landmarks.

Best time to photograph: You can have your session at sunrise or sunset in these spots since there are typically very few people in these spots!

Christopher Columbus Park

Why a Christopher Columbus Park Engagement Session is awesome: Sessions around Christopher Columbus Park provide so many cool backdrops. In the spring the pink trees will be in full bloom and you can get so many fun shots under the tunnel. Then just a few steps away you have some boat views on the Long Wharf if you want a more nautical vibe. Cross the street you have the historic Faneuil Hall showcasing some amazing architecture and then you can head to one of my favorite rooftop spots for some EPIC skyline views featuring the Custom House Tower.

Best time to photograph: Sunrise – Besides the rooftop area, these spots are the best at sunrise. Most times in the afternoon during the summer lots of people enjoy this area and lying on the grass in the park (and Faneuil Hall will be mobbed). I just had a morning session here last weekend and we were the only people around. It was SO fun getting some beautiful spots of Quincy Market without any people passing by. Totally worth the early wake-up!

North End  

couple silhouette sunset photo at Narrows of the Harpeth

Why a North End Engagement Session is awesome: Cute storefronts, skyline views by the Rose Kennedy Greenway, and easy walk to the Christopher Columbus Waterfront Park

Best time to photograph: Sunrise – these areas can get especially crowded so opt for a morning session to feel like you’ve got the city streets to yourselves

Bunker Hill Monument, Charlestown

couple walking holding hands in front of bunker hill monument during their Charlestown engagement session
close up of couple laughing during their bunker hill engagement session in Charlestown Massachusetts
black and white photo of couple smiling looking at each other during their bunker hill engagement session with the Zakim bridge behind them
guy kissing woman on cheek sitting on the steps of a Charlestown apartment during their bunker hill engagement session

Why a Charlestown Engagement Session is awesome: Bunker Hill Monument, cute city streets, and additional ocean/skyline views by the historic Charlestown Navy Yard

Boston Esplanade

Why a Boston Esplanade Engagement Session is awesome: Curl up with your cutie on the boat dock, more skyscraper & water views, plus lots of trees! If you want to see the Boston Esplanade explode with beautiful cherry blossoms, then plan your session for late April to May!

Boston Engagement Photos With A Rustic Vibe: Arnold Arboretum in Jamaica Plain

couple kissing surrounded by flowers during their Arnold Arboretum couples session in Jamaica Plain
couple smiling at the camera surrounded by flowers during their Arnold Arboretum baby moon session in Jamaica Plain
wide shot of a couple by flowers and a stream during their Arnold Arboretum couples session in Jamaica Plain

Why an Arnold Arboretum Engagement Session is awesome: If you are looking for a rustic setting that isn’t too far from downtown Boston, this park in Jamaica Plain is perfect. Lush greenery & lots of trees allow for beautiful fall photos as the leaves change color.

Boston Fenway Park

Why a Fenway Park Engagement Session is awesome: If you’re a die hard Red Sox fan, then share your passion for baseball with a Fenway Park engagement session. It is free to shoot outside of the park, but does require an additional $750 location fee to shoot inside the ballpark for 1 hour. They schedule sessions on weekdays (non-game and non-event days) between 9:00am-4:00pm. 

If you need a rustic setting in the South Shore: Borderland State Park in Easton

Why a Borderland State Park Engagement Session is awesome: Beautiful in any season, the Ames Mansion, rustic trails, and water views.

Additional Fees: Parking- $5 with Massachusetts plates, $20 out of state plates, DCR pass free & a $45 Photography Permit Fee

You can see highlight’s from Laurel & Owen’s Borderland Engagement Session here.

Want a beach engagement session? Head to Duxbury in the South Shore!

Why a Duxbury Engagement Session is awesome: Play in the sand, walk along the water (or get in it!), and snuggle up by the grassy dunes. There are a bunch of great waterfront spots close to the South Shore or head to Cape Cod for more options! Additional Fees: Beach parking varies


Like what you see here? I’d love to capture your Boston engagement session! Feel free to shoot me a message here today to inquire about availability for your session. Dates fill up quick so don’t wait!

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