Beacon Hill is one of the most extraordinary neighborhoods in the United States. In just a handful of blocks, visitors can find a treasure trove of history and beauty along the brick sidewalks and cobblestone streets.

Gaslit lanterns beckon you to explore the streets so rich in cultural importance.

Our Shaka Guide walking tour visits 17 of the best stops in the neighborhood, including historic homes, museums, and even some places made famous through popular culture.

Highlights include the Massachusetts State House, the Museum of African American History, and America's most photographed street, Acorn Street.

Itinerary

1. Robert Gould Shaw and 54th Regiment Memorial

Matt Caracciolo

• Duration: 10 minutes

This bronze relief sculpture recognizes Colonel Robert Gould Shaw and the Massachusetts 54th Regiment, one of the first African-American units in the Union Army during the Civil War. Sculptor Augustus Saint-Gaudens completed the memorial in 1897.

2. Massachusetts State House

Matt Caracciolo

• Duration: 45 minutes

Opened in 1798, the Massachusetts State House is one of the oldest state houses still in continuous use.

Boston's Charles Bulfinch designed the original brick structure, which is considered one of the best examples of Federal-style architecture in the United States.

Within the state house, guided and self-guided tours pass stately rooms, murals depicting famous events of the American Revolution, and the Sacred Cod.

3, Otis House Museum

Matt Caracciolo

• Duration: 5 minutes (longer for the museum's guided tour)

The first of three houses architect Charles Bulfinch designed for Harrison Grey Otis and his family.

Otis was a prominent politician and real estate developer, but his more famous uncle James Otis was a Patriot during the American Revolution, and is credited with coining the phrase 'Taxation without representation is theft."

The home was completed in 1796 and is another excellent example of Federal-style architecture. Tours are available on limited days.

4. Museum of African American History

Matt Caracciolo

• Duration: 1 hour

This museum is housed in the former Abiel Smith School, an African-American school before Boston's schools were integrated.

The museum also includes access to the African Meeting House, completed in 1806.

For decades, this building was home to a church and was a community gathering space. Abolitionists like Frederick Douglass and William Lloyd Garrison preached from the pulpit.

5. George Middleton House

• Duration: 5 minutes

The George Middleton House at 5 Pinckney Street was built in 1786 and is considered the oldest residence still standing in Beacon Hill.

Middleton was a member of the Black community in Boston and a veteran of the American Revolution.

The house is currently a private residence, and there is no public access.

6. Nichols House Museum

Matt Caracciolo

• Duration: 5 minutes (or longer for the museum's guided tour)

The townhome at 55 Mount Vernon Street was designed by Charles Bulfinch and completed in 1804.

The Nichols Family moved into this address in 1885. Their oldest child, Rose Standish Nichols, became a prominent landscape architect.

When Rose inherited the house, she intended the building to become a museum, so she collected art to display in the house.

7. Otis House II

• Duration: 5 minutes

85 Mount Vernon Street is the second house Charles Bulfinch built for the Otis family. It was completed in 1802. The house is a private residence and is not open to the public.

8. Louisburg Square

Matt Caracciolo

• Duration: 10 minutes

One of the most exclusive neighborhoods in America, Louisburg Square has been home to the likes of Robert Frost, Louisa May Alcott, Jenny Lind, and more. It's a pleasant place to stroll and admire the brick townhomes.

9. Acorn Street

Matt Caracciolo

• Duration: 5 minutes

Acorn Street is regarded as the most photographed street in the United States. It's one of the few cobblestone streets left in Boston.

The street is privately owned, so it's best to take pictures either at the top or the bottom of the street. The owners appreciate it when people walk through quietly.

10. John J. Smith House

• Duration: 5 minutes

86 Pinckney Street was home to John J. Smith, a member of Boston's Black community, from 1878 to 1893.

Smith was a businessman and was heavily involved in the Underground Railroad. The house is a private residence and is not open to the public.

11. Lewis & Harriet Hayden House

• Duration: 5 minutes

66 Phillips Street was home to Lewis and Harriet Hayden. The married couple escaped slavery in the 1840s and settled here in Boston, where they became heavily involved with the Underground Railroad.

They used their home as a safe house and were known to be heavily armed. The house is a private residence and is not open to the public.

12. Charles Street Meeting House

Matt Caracciolo

• Duration: 5 minutes (or longer to enjoy the cafe)

Charles Street Meeting House was built in 1807 by Asher Benjamin, a contemporary of Charles Bulfinch and another prominent architect in the Federal style.

The building was home to Third Baptist Church, and then the First African Methodist Episcopal Church. Today, the building has offices and retail inside.

The Tatte Bakery and Cafe on the ground floor is a nice place to rest along the tour and get a snack or coffee.

13. Cheers

Matt Caracciolo

• Duration: 30-60 minutes to enjoy a drink or meal

Originally the Bull and Finch Pub, Cheers is the official pub tied to the popular TV series.

Back in the 80s, television producers were in the Boston area looking for inspiration for their next show set in a down-to-earth pub.

They used the Bull and Finch Pub's aesthetics for inspiration, and filmed the show's opening sequence outside of the pub, though no filming occurred here.

You can visit the original pub in the basement, a closer re-creation of the show's pub in the floor above, or the gift shop.

14. Make Way for Ducklings Sculpture

Matt Caracciolo

• Duration: 5 minutes

Sculptor Nancy Schön designed this sculpture of a family of ducks in 1987. The ducks are based on the classic children's book Make Way for Ducklings by Robert McCloskey. 

15. Good Will Hunting Bench

• Duration: 5 minutes

This bench is featured in the 1997 film Good Will Hunting. Stars Robin Williams and Matt Damon sit and talk on this bench in a prominent scene in the film.

16. William Hickling Prescott House

• Duration: 5 minutes

Built in 1808, 55 Beacon Street was home to historian William Hickling Prescott from 1845 to 1859.

The 2019 adaptation of Little Women was filmed here, as the home of the wealthy Moffat family. Tours are infrequently offered throughout the year.

17. Otis House III

• Duration: 5 minutes

45 Beacon Street is the third and last home Charles Bulfinch designed for the Otis family, completed in 1808.

Otis lived here for 40 years until his death in 1848. The building is currently home to the American Meteorological Society.

Explore Beacon Hill with Shaka Guide

Come join Shaka Guide in Beacon Hill as we explore the next chapter of Boston's history after the American Revolution.

We'll share stories of trailblazing figures, beautiful architecture, and heroic feats in the neighborhood's stations on the Underground Railroad.

It's a perfect and easy companion to the city's famous Freedom Trail.

Take the Beacon Hill Audio Tour with Shaka Guide and explore at your own pace with stories, directions, and must-see stops along the way.

Still planning? Check out our Know Before You Go, Beacon Hill guide to prep for an epic day.

Need help? Email us anytime at aloha@shakaguide.com!

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