My 5 Favorite Engagement Session Locations in Eastern Massachusetts

Massachusetts has so many great spots for photography and sometimes it can be overwhelming selecting a location. To help you, I’ve put together a list of my 5 favorite locations for engagement sessions (of course other types of sessions could be held here).  Whether you are a beach person, city person or nature person, there is a location for you!

1.     Boston Common – Carousel

This is such a fun location – but the key here is timing! Ideally, you want to shoot when there is NO ONE on the carousel so that can be a little tricky. For this session, we planned it on a Sunday evening at 6PM in mid-July. Which was PERFECT because the carousel actually ‘closes at 6PM’! We started the shoot right at 6PM just after the carousel closed, which gave us plenty of time (and light) to then go to a few other spots in downtown Boston.

Boston Carousel 1
Boston Carousel 2.jpg

2.     Beacon Hill

This is a go-to here in Boston. Especially Acorn Street, which is one of the most photographed streets in the city. Because of this, expect to have to wait in line. Yes, I said ‘wait in line’ to take a photo. It can be especially difficult to frame photos without any bystanders in the background. Nothing that a little photoshop can’t take care of, but it certainly can be intimidating doing a dip in front a a dozen strangers. But its totally worth it! Another great spot to stop in Beacon Hill is in front of the State House. It’s a gorgeous building and makes a stunning backdrop.

Acorn Street Boston
Acorn Street Boston 1
Massachusetts State House

3.     Hartwell House

This is a popular spot for photographers, but it is pretty spread out so you don’t feel like you have to wait for a particular shot. It is also part of the Minute Man National Park, so it is well cared for and parking is very easy. One of the reasons I loved this location so much is the variety it offered. The Hartwell House offers a great backdrop, but there are also several historic stone walls in the vicinity. You don’t have to go far to get a variety of shots. If you like trees, fields, history – this is the spot for you!

Hartwell House Concord
Hartwell House Concord
Hartwell House Concord

4.     Preston Beach, Swampscott, MA

I was first introduced to this location by one of my high school senior clients. She suggested it as it was near to her home. I figured we couldn’t go wrong with a beach shoot so I trusted her judgement on this one. And she was right! However, what I particularly love about this spot isn’t actually the beach! It’s the part just above the seawall. It has meandering paths that wander through native grasses and stone work. Its truly beautiful. Plus the warm tones of this location really add to the overall feel of the shoot. Sometimes shooting in ‘less green’ location can really benefit you in that way.

Preston Beach, Swampscott
Preston Beach, Swampscott
Preston Beach, Swampscott

5.     Harborwalk

The Boston Harborwalk is actually quite long and travels through many neighborhoods of the city. The area where I’m particularly fond of is Fan Pier Park. This location is in South Boston, but has great views of Boston Proper. There is a beautiful cobblestone walk which is great for that historic Boston feel. So this location is one of my favorites because it has the historic cobblestone walks, but also has Fan Pier Park which offers some beautiful greenery to explore. My recommendation for this location is try to shoot NOT on a windy day. Being right on the water means more winds in general, and if you have an especially windy or cold day, it can make for a less pleasant experience. This shoot actually was done on one of the colder days of the year. They toughed it out and the shoot was awesome, but I wouldn’t recommend this spot in the colder months.

Meg_Joe Harborwalk.jpg


Recently engaged? Looking for a wedding photographer? Jessie Wyman has been shooting couples and weddings since 2013 and has worked at a variety of venues. Want to know more? Check out her blog or portfolio page for more information or contact her directly at