The possibilities are endless, but as a wedding photographer who calls Boston home, I’m sharing some of the best Boston engagement session locations with you today. Whether you’re looking for water views, iconic Boston landmarks, or green spaces in the city, this list has you covered.

1. Boston Public Garden

For an iconic Boston scene – nothing beats the Boston Public Gardens for your engagement session. This is a beautiful green space in the middle of the city where you can catch hints of the skyline at some angles or completely envelop yourselves in the gardens and flowers. The city does a great job of curating the lawns and gardens so that there is something blooming virtually all year, except when snow covers the ground in winter. The crowds are a factor to think about though so you can’t be shy about snuggling in public if you choose this spot. In order to truly have the place to yourselves – I highly recommend a sunrise session. It’s an early start, but the light is beautiful and the photos will absolutely be worth it!

See more from this sunrise session at Boston Public Garden here!

2. The North End

The North End has something for everyone! You can wander the side streets and find secluded beautiful nooks with gorgeous light., you can embrace the history of the city and snuggle outside of Old North Church and Paul Revere’s Home, you can find water views, and you can end with cannoli or gelato from one of the countless amazing Italian Restaurants that the North End is known for ( I’m a Mike’s Pastry girl all the way)!

See more from this winter North End session here!

3. Arnold Arboretum in Jamaica Plain

Arnold Arboretum is nestled just outside of Boston’s city center in Jamaica Plain and it boasts an amazing and expansive set of grounds with lots of gorgeous trees that bloom throughout the year. It’s the best Boston engagement session location for lush greens and florals and a diversity of beautiful spots all in one place. You’ll find hundreds of lilacs come springtime and fall foliage that is bold and beautiful in the fall, with rich greens and flowering trees all summer long. The Arboretum also hosts several different curated spaces from a small pond, to rolling lawns and stone walls with arbors of flowering vines, to tree-covered paths and city views. Even when the days are beautiful and it gets busy, the Arboretum is large and diverse enough to offer a plethora of beautiful seemingly secluded spaces.

See more from this Arnold Arboretum session here!

4. Rose Kennedy Greenway

The Greenway cuts a partial ring around the outer edge of the downtown Boston area, hugging the harbor from South Station to North Station. You’ll find changing 3d art installations on the paths along with carefully curated gardens. The Greenway offers green space right in the city with easy access to water views, Quincy Market, and the North End. The prettiest parts also happen to be least busy because they’re right off of South Station in the heart of the Financial District. Avoid the 5pm rush hour when everyone’s heading to catch their trains home for the day and you’ll be golden!

See more from this Rose Kennedy Greenway session here!

5. Bunker Hill Monument & Charlestown Navy Yard

Bunker Hill is not only a fun historic landmark in Charlestown, but it is also in the middle of a park nestled in a gorgeous neighborhood and set atop a grassy hill that is perfect for a diverse set of photos with beautiful light. The monument itself is right along the Freedom Trail so history buffs will love it. And it makes for a creamy neutral backdrop for photos! The park is lined with trees that can add some greenery to your photos. A short walk away is the Navy Yard with stunning views of the Boston skyline across the harbor. Like the Public Garden, the monument gets a lot of traffic on nice days so have some patience when you’re there in the afternoons and consider a sunrise session to avoid the crowds.

6. Beacon Hill & Acorn Street

Beacon Hill is full of history, brownstones, flower boxes, brick and cobblestone, and gas street lamps. Its a romantic neighborhood right off of Boston Common. True to it’s name, the neighborhood is set on a steep hill so be prepared with a pair of sensible shoes for walking between places and change into heels once you’re in a spot for photos. Acorn Street, the sweet cobblestone street pictured below, is the most photographed street in MA (and maybe even the country!).

However, it is a private street that families live on. So make sure to be quiet and respectful if you go there to take photos. And be prepared to play nicely with other photographers and tourists as this street is famous! Make sure to take your time exploring the side streets around Acron Street. There are endless alleys, nooks, and crannies all around Beacon Hill that make for great photo ops and will be less crowded. End on Charles Street for some food or shopping – it’s one of the cutest streets in the city!

7. Back Bay & Comm Ave Mall

The Back Bay is an historic neighborhood full of gorgeous turn-of-the-century brownstones and intricate wrought iron fencing. The stone steps, window planters, and decorative doorways throughout the Back Bay lend a special charm to the neighborhood and make it the perfect place to stroll for your engagement photos. The Comm Ave Mall (another location on this list!) runs through the heart of the Back Bay and it sits adjacent to the Public Garden so you can easily get a wide diversity of photos if you start here.

8. JFK Library & Museum in Dorchester

The JFK Library is a modern white building with a two-story glass foyer facing the water. It sits along the Harbor Walk in Dorchester and has cement stairs and a brick patio area as well. Along the Harbor Walk you’ll find views of the Boston skyline, a dock and a small tree-covered public park that all make for great photos. This spot is a perfect mixture of modern neutrals and natural elements and being south of the city center, you’ll find free parking on site and much fewer people around, no matter the time of day.

See another JFK Library session here!

9. The South End

The South End is full of adorable brownstones, gardens, and tiny parks that peak through views of the Boston skyline. Strolling through the neighborhood, stopping by your favorite local eatery, and snuggling in the little nooks and crannies is beautiful and romantic rain or shine!

10. Charles River Esplanade

The light on the river is gorgeous whether you go for a sunrise session or a sunset session, which is why the Esplanade makes my list of the best Boston engagement session locations. And the number of beautiful spots all within two minutes of each other is great for adding diversity to your portfolio of final images. From the decorative seating, to the dock on the water, to the grand bridge and lush greenery everywhere you look, the possibilities are endless. And if you want to head over to the Public Garden or into the Back Bay for some more shots, it’s as easy as crossing Beacon street the footbridge!

The most important thing when choosing your engagement session location is to pick a spot meaningful to you as a couple.

That way, whether you end up in Boston for your engagement session or elsewhere, you end up with photos that are meaningful and sentimental, as well as beautiful. Maybe it’s where you first met, or where you first said I love you. Or maybe it’s your neighborhood where you’ve made your life together. Download my free worksheet to help you determine which place will be best for photos and full of meaning for you and your soulmate to have your engagement photos taken!

And if you’re still searching for a photographer to capture your love story – reach out to me and we’ll set up a time to chat!