What to Photograph in Beacon Hill

14 Photogenic Spots in Beacon Hill

Beacon Hill is a sight for sore eyes. The neighborhood is steeped in rich history, yet time has ultimately stood still here. Original homes and distinctive features dating back to the 1700s have been well-preserved and maintained, and the quaint neighborhood carries an unmistakable allure.

With antique, gas-lit lamps, cobblestone streets, red brick sidewalks, narrow alleys and hidden gardens, it’s no wonder residents and tourists alike flock to Beacon Hill. If you have the opportunity to explore the charming neighborhood, here are 14 of my favorite places to photograph.

1) Acorn Street

Let’s get this one out of the way early. Acorn Street, the most photographed street in Boston (and some say in the United States), is typically at the top of everyone’s must-see list. It’s the narrowest street in Boston, featuring some of the city’s only true forms of cobblestones in significant quantity. Now home to the wealthy, the street ironically once housed artisans and service people who worked for the nearby mansion-dwellers.

A few other things to notice:

  • On the north side of the street, the brick walls enclose some of Beacon Hill’s hidden gardens.
  • The iconic, prominent flag is actually a Civil War-era Union flag with gold trim.
  • More than one home has an acorn door knocker!



Between West Cedar Street and Willow Street, parallel to Louisburg Square

2) Willow Court

Once you check Acorn Street off the list, you can’t miss the alley at the top of the hill, on Willow Street. This private courtyard is especially fantastic in the fall, with pops of seasonal, rustic colors contrasting against red brick . Don’t forget to look up, too: The mesmerizing fire escape is one of my favorites.


Perpendicular to Willow Street, atop Acorn Street

3) Louisburg Square

Named for the 1745 Battle of Louisburg, this is one of the most expensive and most prestigious areas in the United States. I’m talking $13 million for a home

Every resident within this exclusive enclave receives a parking spot (a rare opportunity in Beacon Hill) and a key to the well-maintained central garden, surrounded by a wrought iron fence and cobblestone streets. U.S. Secretary of State John Kerry currently lives at 19 Louisburg Square, easily identifiable by the American flag atop his home. You’ll also notice a beautiful stained glass window on the Pinckney Street side of the corner home, which used to be a chapel; it’s now Mr. Kerry’s kitchen.

For the past 93 years, a festive bell-ringing and caroling event takes place in Louisburg Square on Christmas Eve. Don’t miss out if you’re around; the square is an absolute winter wonderland.

John Kerry’s home in Louisburg Square

Bordered by Pinckney Street and Mount Vernon Street

4) 29 A Chestnut Street

If you read my “Hidden Treasures of Beacon Hill” post, you’re already familiar with this spot. 29 A Chestnut possesses an elaborate garden that’s visible from the street – a rare exception to the mostly hidden gardens within Beacon Hill. Other key characteristics include brick laid in Flemish bond, a side entrance and treasured lavender windows.

In the winter, the space is decked with seasonal Christmas fare, and in the spring, the 25-foot-wide garden is accented by tulips, bright flowers and trees. 29 A Chestnut was once occupied by Shakespearean actor Edwin Booth (yes, brother to the evil Booth).


29 A Chestnut Street

5) Scarlett O’Hara Home

Hidden on a private alley off Revere Street is a two-story, Greek Revival-style home, with a brilliant white façade and iconic columns. The home starkly contrasts against the Federal Style, brick homes surrounding it.

Based on the few records of this home, the façade was created more than 30 years ago as a creative way to obscure a concrete wall from public view, creating an optical illusion. A trompe l’oeil, as the French call it.


Revere Street, at Rollins Place

6) Smith Court

This is one of my newest fascinations in Beacon Hill, brought to my attention by friend Matthew Dickey (@_madickey_) during a Historic New England tour. Formerly called May’s Court, Smith Court (1846) was the focus of Boston’s black community for most of the 1800s. Today, the Museum of African-American History stands at the beginning of Smith Court.

As you walk into the cul-de-sac, you’ll pass the William Cooper Nell House on your right, a rare surviving wooden residence built in 1799. Nell was the first published black historian, and he resided in 3 Smith Court from 1851 to 1865. The home at 5 Smith Court, a three-story building from the early 1800s, was once owned and lived in by George Washington. The building remained with his family till 1917.

Here’s the kicker: Do not turn around back toward Joy Street once you’ve seen enough in Smith Court. March all the way to the “dead end,” and hook a left through the narrow Holmes Alley! This used to be the site of a perpendicular system of rope walks, dismantled during the 1700s. Keep following the path, and you’ll end up on Russell Street.


Smith Court, at Joy Street

7) Sunflower Castle

Sticking out like a sore thumb amid the surrounding Federal and Colonial buildings, the bright yellow, Queen Anne-Style home built in 1840 stands tall. Above the front door, you can spot a black iron griffin and a wooden carving of a sunflower. The first floor is painted bright yellow.

In the 1800s, the home was occupied by watercolor artist Gertrude Beals Bourne and her husband, architect Frank Bourne. The now-master bedroom was once dubbed “The Artist’s Studio – Sunflower Castle”


130 Mount Vernon Street, at the corner of River Street

8) 73 Chestnut Street

Yet another oddity among mostly brick buildings is Beacon Hill’s very own baby blue building. Built in 1884, the two-story, former carriage home boasts FIVE fireplaces. Most notably, the home is hidden behind a storefront, formerly an antique shop. The house and storefront were sold for a cool $3 million earlier this year.

Tip: If you ever see this house without a car parked in front of it, fire away on your camera. A rare event! The below took me three years to capture!


73 Chestnut Street

9) Harrison Gray Otis House

You truly can’t miss this one. Literally speaking. The second Harrison Gray Otis house is the only remaining freestanding mansion within Beacon Hill, built between 1800-1802. Otis was a businessman, lawyer and Federalist Party leader, and he worked with the famous Charles Bulfinch on all three of his Beacon Hill Federal Style homes.

Typical of Federal Style homes, the property is a large, symmetrical three-story square, with brick walls laid in Flemish bond. Otis sold the home in 1806 in search of a larger property! Today, the house is listed on the National Register of Historic Places.


85 Mount Vernon Street

10) Spruce Court

Quite honestly, I can’t find any history on this property. But, it’s so perfectly quaint and pleasant to the eye that I must share with you. I love shooting this one!


Spruce Court, perpendicular to Spruce Street, parallel to Boston Common

11) 110 Myrtle Street

Similarly, not too much information available on this building, aside from the fact that it was built in 1897 – clearly labeled on each side of its façade. This building intrigues me, as red brick dominates the neighborhood, but once you turn the corner here, you’re met with yellow and pops of GREEN!


110 Myrtle Street, on the corner of Grove Street

12) Garden Street

Although this isn’t a specific property, I highly recommend standing atop Garden Street and looking down. The trees create an incredible canopy that stun throughout all four seasons. In the summer, they’re bright green, and in the winter, perfectly snow-topped.


Garden Street, at Phillips Street

13) Boston Fire Department

Engine 4, Ladder 24 is a charming (and hardworking!) fire house, opened in 1965. The department covers not only Beacon Hill, but also the North End, Downtown and Back Bay. Stand across Cambridge Street, by the first Otis home, if you plan to photograph the building.

Thank you for your service!


200 Cambridge Street

14) Liberty Hotel

Behind the Charles MGH red line train stop is the Liberty Hotel – so why am I sending you to a luxury property amid brick mansions from the 1700s? Well, the now-hotel was formerly the Charles Street Jail, designed in 1851 by Gridley James Fox Bryant. The prison was built with a 90-foot rotunda, with jail wings stretching out in a cross; prisoners were segregated by class of crime. This historic structure, central atrium and famed rotundas still exist today.

The prison, once housing inmates Boston Mayor James Curly, Malcolm X, and Sacco and Vanzetti, was forced to close in 1973 by federal court order and shut its doors officially in 1990. If you get a chance to check it out, grab a drink at the ground-level bar, Alibi, which still features preserved wrought-iron work previously used as jail cells.

215 Charles Street

Although not technically Beacon Hill, make sure to the visit the adjacent landmarks: Charles River Esplanade, Public Garden and Boston Common.

What’s your favorite spot to visit in Beacon Hill? Did I miss any favorites of yours?



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