• Jenny Penland

Travel Tips ‣ Shooting on Acorn Street

How to get the perfect shot (and soak in the history) of the most photographed street in America.

Located in the heart of Beacon Hill, Acorn Street is purportedly the most photographed ally in America - and having been erected during the 1700's, one of the oldest and last *true cobblestoned rows left in America.


If you're considering visiting, rest assured you'll feel like you walked right into the Revolutionary Era when you walk the path. It's situated just south of Louisburg Square and is rich in Black History and the racial progress of our nation. Once inhabited by freed slaves who played a pivotal role in the Underground Railroad, Acorn Street now houses some of the most coveted real estate in all of Massachusetts.


I’m not sure when or how I came across images of it, but long before (years and years before) I had any idea we were moving to Boston, I wanted to do preppy, plaid Christmas pictures on Acorn Street. And man. Dream fulfilled. But having checked the box, here's some tips I'd pass on for those who also want to snap some pictures at this beautifully historical spot.


1. Be prepared to wait

No matter when you go, there will usually be some sort of a crowd. Expect to wait a few minutes, expect people to be waiting to shoot after you (and expect them to awkwardly watch while you take yours - though in our case, this could have been the out-of-season plaid and stacks of matching packages).


2. Avoid going at the busiest times

Your best bet is to go on a weekday, closer to dusk - but either way, this is not the location to do a full photoshoot (we snapped pics for five minutes, then took the rest of our photos in the surrounding areas.


3. Know your surroundings

Acorn Street isn't comprable to say, taking pictures at Lombard Street in San Francisco. The one-block-long road is just about the width of a car and because it is still in use, you may have to stop and move to allow for locals to drive through….Or park in front of their house, as this is still a residential street. So be mindful of the people who live there. Avoid accidentally shooting through their windows or getting them in the background of your pictures without their consent. The residents do a fantastic job decorating their stoops for each holiday, making it a great backdrop for seasonal photos (taken in *that season - i.e. if you shoot Christmas card pictures in October, be prepared for pumpkins!)


4. Wear shoes you can walk in

Located in aptly named Beacon Hill, Acorn Street is also much steeper than you could possibly imagine and is a *true cobblestone street, making it incredibly uneven and irregular. So unless you are like me and are willing to break an ankle for the perfect shot, leave the six inch stilettos at home.


5. Bring a wide angle lens

Where you are shooting (and where you are shooting from) are cramped quarters, so bring a wide angle lens to capture the full length of the row houses, and shoot from both the top and the bottom of the street. This means waiting in line twice, but it is worth it, I promise!



These two images above were taken within thirty minutes of one another - The left being taken at the top of the street and the bottom on the other end. This allowed us to get two totally different types of lighting (and as I said, going around dusk for the golden hour was key!) but also gave us a few more minutes of shooting without encroaching on the other visitors.


6. Take a stroll around Beacon Hill

Taking pictures on Acorn Street is a one-two punch, but all of Beacon Hill is so picturesque - so don't fret. We walked down the block and took a few more images by the shops and brownstones - but it's also in close proximity to the Common, which would make a second — and much more open — location for photos.

7. Soak in the history

#Instagrammable? Indisputably. But more importantly, Acorn Street seeps of historic abolitionist activism in antebellum America. Take some time to learn about the area before or during your visit. Walk down to the Museum of African American History, located at the restored African Meeting House. The museum is open from 10:00 a.m. to 4:00 p.m. every day except Sunday, and a calendar of events is available on its website.









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