When people ask me what my favorite thing about living in Boston is, one of my top answers is always “the history!” Living in Greater Boston is like participating in a giant history lesson. Everywhere you turn there are plaques, monuments, and historic sites. I married a history buff who has been exposing me to Boston historical landmarks for the last decade. I’m able to retain history lessons so much better when I get to experience them! Whether you are visiting Boston for the first time or are looking for some local family fun, this guide includes many must-see historical landmarks in Boston. 

Check out our curated Boston historical sites itinerary, then read on for more great info on visiting Boston to soak up all its history!


The easiest starting point for a historic landmark tour in the heart of Boston is the Freedom Trail. This 2.5-mile trail starts in the Boston Common and winds through the city to the harbor as you follow the red brick path markers. Paid tours are available but not required. Plan for a full day to really soak in the Freedom Trail, and allow for sightseeing along the way. 

There are 16 significant markers along the Freedom Trail, but these are some of the infamous stops you will want to prioritize! 

Boston Common

Located downtown, the Common is the oldest city park in the U.S.! This recreation area is home to Frog Pond, where local children keep cool in summer and where everyone enjoys ice skating in the winter. You will also find plenty of green space to relax and play, plus street vendors, the Boston Common carousel, and the popular Tadpole Playground. There are public bathrooms located in the visitor’s center.

Massachusetts Statehouse

Take a photo with the Massachusetts state capitol building! Located right across from the Common in Beacon Hill, you can’t miss the shimmering gold dome standing out in the Boston skyline. Also known as the “New State House,” you might even see a peaceful protest or local news crew out on the front steps.

Granary Burying Ground

Stroll this historic cemetery, where some of our country’s most notable historic figures are buried. Keep an eye out for the headstones of Sam Adams, John Hancock, Paul Revere, and so many more. 

Old State House

Really get a feel for how the city has grown up around its history as you gaze at the oldest surviving public building in Boston. This building witnessed the Boston Massacre bloodshed and later was the site of the first reading of the Declaration of Independence. For a more in-depth tour, purchase tickets for the museum. 

Paul Revere’s North End House

See where Patriot Paul Revere resided during the American Revolution. A budget-friendly tour of the Revere family home costs $6 for adults and $1 for children.

Old North Church

“One if by land, two if by sea.” Sound familiar? After touring Paul Revere’s home, walk a few blocks over to Boston’s oldest church. This famous church and steeple were the first stop on Revere’s “Midnight Ride” to Lexington. 

USS Constitution

Also known as “Old Ironsides,” this is the oldest commissioned ship in the country. Come aboard and explore this floating museum. Adjacent to the USS Constitution is another must-visit: the USS Cassin Young, a World War II destroyer ship.

Bunker Hill Monument

Learn more about the site of one of the first major battles in the Revolutionary War! And climb the 294 steps to the top of the monument to take in breathtaking views of Boston and surrounding areas. 

*Please note, while the monument grounds are open, the monument is closed for climbing at the time of this publication. Call ahead for the most current information. 

Black Heritage Trail & Museum of African American History

Learn more about Boston’s journey to abolish slavery, fight for equal rights (including equal access to education), and house freedom seekers along the Underground Railroad. Walk the 1.6-mile trail to explore important historical landmarks in person, or enjoy time at the Museum of African American History. 

Boston Tea Party Ships and Museum

Take a step back in time on this floating museum! Experience exhibits, witness re-enactments, and hear from historians on this critically acclaimed attraction. 

Boston Public Library

Established in 1848, this sprawling building in Copley Square is so much more than a library. Take in the exquisite architecture and artwork, sit in the serene courtyard, have some refreshments in the tea room or cafe, let your kids explore the children’s area, and, of course, take in the staggering collection of books.

Castle Island

Perfect for families and enjoyed by locals year round, this 22-acre urban park is home to Fort Independence built in the 1830s, multiple walking path loops, beach shoreline, and a playground. Take in stunning views of the harbor, watch ships and ferries sail out to sea, and view airplanes taking off and landing at Logan Airport.


Visit the only remaining Chinatown in New England — and one of the largest Chinatowns in the country! You can’t miss the beautiful China Trade Gate landmark, generously donated to the city of Boston by the government of Taiwan. Browse the shops and dine at authentic Chinese restaurants. Located just outside the China Trade Gate is Boston’s Chinatown Park on the Rose Kennedy Greenway, where kids can burn off some energy. 

Fenway Park

A trip to Boston would not be complete without a stop at America’s oldest and “most beloved ballpark.” Fenway has been home to the Boston Red Sox since 1912. Even if the team isn’t playing a home game in town, learn more about the park’s fascinating history by booking a 60-minute tour. Even the youngest of baseball fans will enjoy exploring Fenway.  


Union Oyster House

The oldest restaurant in Boston and the oldest restaurant in continuous service has borne witness to the city’s establishment and a historic revolution — and it has accommodated numerous historical figures. This includes, but is not limited to, John Adams, Louis Phillippe, and John. F. Kennedy. Walk around to gain more insight into the restaurant’s history. Dining at Union Oyster House starts with their traditional cornbread, a perfect pairing with a hearty bowl of New England Clam Chowder. The menu is large and the specials are always changing, guaranteeing something for everyone while you soak up the incredible atmosphere.

Quincy Market

Just a few steps across from Faneuil Hall is Quincy Market. The food hall is the perfect place to grab a quick bite to eat at one of the many food vendors. With so many food options, the pickiest eater is sure to find something that satisfies. No need to wait on a table at this location — grab an open table inside, or enjoy your food in the fresh air outside the market.

Green Dragon Tavern

A Boston favorite since 1654! Dine in the same space where the Revolutionary War was planned out. Notable diners here include Paul Revere, John Hancock, and Daniel Webster. Stop in to enjoy Irish-American cuisine and all the New England classics. 

The Bell in Hand Tavern

America’s oldest continuously operating tavern has been serving Boston since 1795. It is still a Boston local favorite for a great meal and a cold beer.

Omni Parker House

Home of the Boston cream pie, the Omni Parker House has been a Boston staple since the late 1800s. It is currently located inside the Omni Hotel. The Parker House has produced famous chefs such as Emeril Lagasse, Jasper White, and Lydia Shire. There is a dress code to be aware of for this fine dining experience, and reservations are recommended. 


Boston is very walkable and stroller friendly. Riding the T is a helpful option for getting from one side of the city to another. Subway stations are easily accessible and located throughout the city. Rideshare apps such as Uber or Lyft are easy to use in the city as well. 


Boston has many parking garage options. Keep in mind most of them offer reduced rates for weekend parking.

Boston Common Garage

0 Charles Street, Boston, MA

This garage is located directly under the Boston Common. It is a central location to the Public Garden, Beacon Hill, and downtown.

Post Office Square Garage

112 Congress Street, Boston, MA

This garage is located on the eastern side of downtown and is just a quick walk to the harbor. 

Dock Square Parking

20 Clinton Street, Boston, MA

Located right off I-93, this garage places you in the heart of Boston just steps from Quincy Market and the North End. 


Acorn Street

Known as “the most photographed street in Boston,” this cobblestone road lined with row houses transports you back in time to how the city used to stand. Located in Beacon Hill, Acorn Street is one of the last remaining authentic cobblestone streets in the country. 

Brattle Book Shop

You will know immediately if you stumble upon this charming used book shop that spills over into the alleyway beside it. Established in 1825, this is one of the largest and oldest book shops in America.

Fan Pier Park

In order to truly take in the city’s breathtaking landscape, visit Fan Pier Park in the Seaport. You will get a sense of the city’s history as old architecture has blended with the new growth of the city over the centuries. 

Swan Boats

This Public Garden gem has been thrilling Bostonians young and old since the late 1800s. Have a seat on these popular boats as a staff member navigates you through the lagoon with city and park views.


Omni Parker House

Enjoy old-world charm with modern luxury at this iconic Boston hotel, which has been accommodating guests since 1855. 

Copley Square Hotel

Built in 1891, this hotel has hosted guests such as Babe Ruth, Ella Fitzgerald, and Billie Holiday. The hotel has undergone modern-day renovations, promising a comfortable stay.

Loews Boston Hotel

This Back Bay hotel served as the Boston Police Department Headquarters throughout the last century. Black and white photographs, as well as clever restaurant and bar names, pay homage to this building’s past life. 


Faneuil Hall

For 270 years, this historic site served as an open forum meeting hall and marketplace. Visitors can still shop at more than 40 local businesses inside the Faneuil Hall Marketplace. And we can almost guarantee you will come across street performers outside Faneuil!

Boston Public Market

This indoor, year-round marketplace features dozens of local artisans. You will find New England-grown produce, as well as specialty items. Trust us, you will want to stop in for a box of authentic maple candy or saltwater taffy. This spot is perfect for unique souvenirs that support local small businesses! 


Baby wear or bring a stroller if you are experiencing Boston with young kids. Downtown can be very crowded and overstimulating with all the loud city noises. 

Ask for help! We’ve all heard the cliche stereotypes about unfriendly New Englanders, but nothing could be further from the truth. If you are turned around or need help, ask for it! A local will be happy to show off our beautiful city for you.

Keep in mind LOTS of people work downtown. On weekdays, there is a rush for the T right around 5 p.m. with local professionals anxious to get home for the day. Keep in mind the trains and train stations will be busier than usual right before and right after normal business hours. 

Try this sample itinerary for a tour of Boston’s best historical sites!

Shannon Gibson
Shannon started following Boston Moms on social media before she even lived in the Boston area! She credits her passion for the brand to the way it served her personally before she ever contributed to it. Though Shannon moved to Boston to support her husband’s career, Boston Moms was the unexpected gift and opportunity she had no idea was waiting for her. Shannon is mom to Elizabeth (2016) and Anderson (2018). She has been married to her husband, Benjamin, since 2012. Benjamin is a filmmaker and owner of Boston production company Magnus Films. In her free time, Shannon enjoys going to the beach, browsing antique stores, hiking with her family, traveling, reading, and watching movies with her husband.