Kristen Swain Photography



new england families, COUPLEs, and landscapes

Mother and father each holding a child in front of green trees.

Favorite Locations in Boston for Fall Family Sessions


October 16, 2023


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Autumn is one of my favorite times of the year to get outside for family and engagement sessions — being a New England-based photographer, I’m spoiled by the beautiful colors and scenery that greet us around this time every year. With fall photo sessions in full swing, I put together a list of five places I think make the best locations for fall photos as the leaves change and the sun sets ever earlier.

1. Arnold Arboretum 

Spanning over 200 acres across Jamaica Plain and Roslindale, the Arboretum is truly an endless array of color and botanical beauty. It’s more than just a park — it’s part of a Harvard research institution, and is home to trees, vines, plants and flowers from not only New England, but around the world. The opportunities for photos are endless; there are woodsy, sun-streaked paths, streams, hills, shrubs, and flowers. It’s great for kids too, with plenty of space to run, large rocks and fallen tree trunks to climb on, and gorgeous – and huge! – fallen leaves to collect.I never tire of shooting at the Arboretum – it’s beautiful in all seasons.  The rapid changes we witness here in the fall, especially, mean that no two sessions look the same. 

2.  Boston Public Garden

The oldest (and quite possibly the most beautiful) garden in Boston, The Public Garden is a backdrop that oozes elegance and natural beauty. There are many opportunities for great photos here, including on the iconic bridge that crosses the Duck Pond, in front of the flower beds, underneath the giant weeping willows, and on the paved paths that wind through the garden. Kids in particular love being able to wave to the geese and swans that frequent the pond!

The Public Garden captures the feel of downtown Boston, but also acts as a natural oasis from the hustle and bustle. I recommend this location highly to anyone who wants their photographs to reflect without question that they are in Boston (this is a common request from families who have moved to Boston recently, and those who just haven’t incorporated much of the city they love into their photos in a while). One drawback of this location is that it does get very busy here, and it can be hard to avoid having other people in the background of your photos in certain areas within the Garden. The best way to avoid the crowds is with a sunrise session. Now, I know that means a very early start to your day, but trust me on this one.  You truly can’t beat having the place yourselves, and that soft morning light just after the sun has risen over the horizon is pure magic. Fall is THE best time to do a sunrise session, if you’re ever going to do one, because there are a few short weeks every fall (this year the dates are October 18th through November 4th) when the sun rises at 7am or later.  

3. The Waterfront 

No matter what, waterfront locations always tend to lead to breathtaking photographs! Two of my current favorite spots are the Seaport in downtown Boston, and Castle Island in Southie. 

The Seaport provides amazing lines and structure (great for photos!), lots of light reflection from all those glass buildings (also great for photos), and all of it right alongside the water with great views of downtown Boston to boot.  This is a fun spot for kids with lots of stairs to climb and descend, plenty of grass patches for some play, and we can make the entire session a moving one – we’ll get great photos at every turn and we’ll be moving so much and having so much fun, it will be over before you (or the kids!) even know it.

The Seaport doesn’t offer a ton of foliage (although there are little pockets here and there, as well as plenty of apartment buildings and restaurants that put out some nice fall decor that I’ve incorporated in photos in the past).  Another waterfront location that offers a little more color is Castle Island in South Boston. There’s a lot to love about Castle Island, including gorgeous trees with plenty of color on display, a large playground for after the session, and unbeatable sunsets. The castle itself also can help block harsh light before golden hour, and makes a fun backdrop for a few photos. 

4. The Fells

The Middlesex Fells spans multiple towns north of Boston, including Winchster, Medford, and Melrose, so it can be a convenient location for families hailing from any of these areas.  I’ve used one particular trail along Spot Pond as a location for family photos a number of times over the last couple of years, and the results are consistently great. My favorite trail (which a client introduced me to a couple of years ago!) leads to an old stone barn that is a fun place for the kids to run around and throw some leaves in the air.  Like the Arboretum, the colors in this area change quickly, which keeps it fun and interesting.  Another advantage of this particular location is that it works well for both sunrise and sunset sessions (if I can ever convince you it’s worth it to get up early and get ready in time for photos starting at 7am – I’ll keep trying!).

5. Your Neighborhood (Or Backyard!)

Sometimes, the best views are right in your own backyard. There is so much natural beauty surrounding a New England fall that no matter where you’re located, you can get some amazing shots of you and your family while staying close to home. In the city, I really love Beacon Hill and the South End — the falling leaves perfectly compliment the red brick buildings and cobblestone streets, and the neighborhoods are quaint and tidy. An added bonus is that you’ll often feel more comfortable in your own neighborhood vs a new location, and an element of familiarity can be relaxing, particularly when taking pictures with little ones. 

Having your photo shoot in your backyard or simply on a neighborhood walk is a fantastic opportunity to make some lasting memories in the place you call home; the sentimental value of photos like these makes them perfect as prints and gifts, too. Plus, there’s nothing easier than being able to simply walk outside and get some portraits done right outside your door! 

Want to make sure you hear all about special events like fall mini sessions, holiday sales, and more? Head over here and sign up for my mailing list – the best way to ensure you’re staying up to date with KSP news and special offers. (The occasional appearance of my name in your inbox also serves as a helpful reminder to move booking your session to the top of your to-do list!)

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