North End Boston Harborwalk Engagement Session

10 Waterfront Engagement Session Locations in Boston

I’m so happy you landed here and are interested in a Boston engagement session! I’ve compiled a list of 10 waterfront engagement session locations in Boston. If you’re hoping for a view of the water or skyline, this is a great place to start. Feel free to browse all of our engagement sessions on our blog to see many more location options around New England.

MIT Sailing Pavilion

There’s a bike path along Memorial drive on the Cambridge side of the Charles River. The entire path has wonderful views looking across at Boston, the Prudential Center and Citgo sign. The MIT Sailing Pavilion is right across from MIT and easily accessible. Click here to see more from this session.

MIT Sailing Pavilion Engagement SessionMIT Sailing Pavilion Engagement Session

Christopher Columbus Park

Besides the Public Garden and Beacon Hill, Christopher Columbus Park may be the most popular spot in Boston for engagement photos. There’s good reason for that. You’re right on the Rose Kennedy Greenway, and across from Faneuil Hall. Columbus Park itself is beautiful, with the Trellis and Rose Garden but I love the waterfront area especially. There are always boats coming in and out of the harbor and the sunset from Columbus Park often looks like cotton candy for some reason 🙂 Check out more photos from Columbus Park and the North End.

Columbus Park Engagement SessionChristopher Columbus Park Engagement Session

Harborwalk Engagement Session

Between Lewis Wharf, Long Wharf and Central Wharf there are endless photo opportunities along Boston’s Harborwalk. It’s my favorite part of Boston, because it just seems to go on forever. Once you go all the to the end of a wharf you have a panormaic view of the harbor, but you can often turn around and see the skyline as well. See more photos from the Harborwalk here and here.

Harborwalk Engagement SessionHarborwalk Engagement Session

Carson Beach in South Boston

If you’re looking for a sandy beach close to the city, Carson Beach is your spot. Located in South Boston, there’s typically plenty of parking and it’s a great spot to have a quiet moment or go for a walk.

Carson Beach South Boston Engagement Session

Carson Beach South Boston Engagement Session

Piers Park in East Boston

Piers Park is one of my favorites. There’s some really great trees and paths to walk around, but then it completely opens up as you walk down to the water’s edge. The view of Boston’s skyline from Piers Park can’t be beat. See more from Piers Park here and here.

Piers Park Boston Skyline Engagement SessionPiers Park Boston Engagement Session

North Point Park

This is one of my new favorites that I just discovered last year. North Point Park in Cambridge sits between the Museum of Science and the TD Garden. It also connects to Paul Revere Park via a path under the Zakim Bridge. It’s a huge park, which reminds me a little of the Public Garden (think dangling willow trees). But it’s much more open and has scenic views of the river & skyline. See more from North Point Park.

BONUS TIP: There’s a super cool skate park under the Zakim Bridge. Bring your board and try out your skills, and don’t mind that smell, it’s a “skunk” 🙂

North Point Park Boston Engagement Session

There’s the Zakim Bridge in the background.

North Point Park Boston Engagement Session

Charles River Esplanade

If you go here in the summer, you’ll be dodging cyclists and runners, which is actually kind of fun. The esplanade is a popular spot for everyone to relax or work out in the city. Because of this I feel like the Esplanade is more like Central Park in NYC that the Boston Common is. The esplanade is one of the best waterfront engagement session locations in Boston.

Boston Esplanade Engagement Session

FUN FACT: Kristen and I had our first unofficial date on July 4 at the Hatch Shell (seen in the background). The Beach Boys played with John Stamos, and hundreds of thousands of people were crammed onto the Esplanade to watch the fireworks.

Boston Esplanade Engagement Session

Charlestown Navy Yard

There’s no subway stop to Charlestown, but that’s the only downside. Hop in an Uber and head over to the Charlestown Navy Yard for a really cool spot for your engagement session.Lots of old brick, plenty of history makes and a lot less tourists make this a great place to consider for a photo session. There’s a small park which you can see more of here, and a great view of the skyline over by the Pier 6 restaurant.

BONUS DATE NIGHT TIP: You can park at Pier 6 and take a quick free water shuttle over to ReelHouse. The views are great and the food is wonderful.

Charlestown Navy Yard Engagement SessionCharletown Navy Yard Engagement Session

Fan Pier

Fan Pier is super iconic in Boston. The skyline and the Old Northern Avenue Bridge make this a scenic and tourist-filled spot in the summer months. However if you go in Winter like we did in the photo below, you’ll have the place all to yourself!

Fan Pier Boston Engagement Session

BONUS TIP 🙂 A short 5 minute walk from Fan Pier is free access to the Observation Deck at Independence Wharf. There are awesome views of the seaport and wharf below.

Castle Island

Castle Island is a great spot to just hang out for the day. The planes fly right overhead. There’s beach on one side and a rocky area next to an old fort on the other. There are so many unique spots to take photosWith free parking it’s easily accessible right in South Boston. See more from Castle Island here. I hope you’re inspired with this list of the 10 best waterfront engagement session locations in Boston!

Castle Island South Boston Engagement SessionCastle Island South Boston Engagement Session-59

Let’s start planning your engagement session!

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