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As one of the oldest cities in the United States, Boston is known for its rich history and significant role in American independence. Boston is popular for its walkability, diverse neighborhoods, and mix of modern amenities and historic charm.

You'll find a wide variety of attractions in Boston, including historic sites, world-class museums, beautiful parks, and exciting sports venues. In this article, I will share my favorite historical things to do in Boston and give you some inspiration and advice on how to fill your Boston itinerary with the best activities.

With so many options, you'll find yourself immersed in the rich tapestry of historical experiences that make Boston a truly unforgettable destination.

Immerse Yourself in the Isabella Stewart Gardner Museum

One of my favorite places to visit in Boston was the Isabella Stewart Gardner Museum. Opened in 1903, the museum was founded by Isabella Stewart Gardner, a wealthy American art collector, philanthropist, and patron of the arts. She designed it to resemble a 15th-century Venetian palace with a stunning courtyard and personally curated the art collection.

The museum houses a diverse collection of more than 7,500 works of art, including paintings, sculptures, tapestries, manuscripts, and decorative arts from around the world. The collection spans European, Asian, and American art, with works by artists such as Rembrandt, Titian, Michelangelo, Raphael, John Singer Sargent, and others.

Famous Art Heist
The Isabella Stewart Gardner Museum is the site of one of the most famous art heists in history. In 1990, thieves disguised as police officers stole 13 works of art from the museum, including works by Vermeer, Rembrandt, Degas, and Manet. The stolen pieces are valued at over $500 million, and the case remains unsolved to this day. This incident has added an element of intrigue and mystery that draws people to the museum.

Isabella organized the collection according to her personal vision, which remains unchanged to this day. The layout of the museum feels more like a journey through history and different cultures than a traditional gallery experience, making your visit truly unique.

The free audio guide was extremely informative and helpful in understanding Isabella, her special connection to this museum, and its development to this day. The three hours I spent at this museum were some of the best hours I spent during my entire trip to Boston.

Visit the Boston Tea Party Ships & Museum

Another experience I highly recommend adding to your Boston itinerary is the Boston Tea Party Ships & Museum. Unlike traditional museums, the Boston Tea Party Museum offers a highly interactive and theatrical experience dedicated to one of the most pivotal events leading up to the American Revolution: the Boston Tea Party of December 16, 1773. Costumed interpreters playing the roles of historical figures such as Samuel Adams and Paul Revere guide visitors through the events leading up to the Boston Tea Party. In 90 minutes, visitors relive the dramatic events that shaped American history.

Not a Drop of Tea Was Consumed at the Boston Tea Party
On the night of December 16, 1773, more than 340 chests of British East India Company tea weighing over 92,000 pounds (about 46 tons) were dumped into Boston Harbor by American colonists. Although called a "tea party," no tea was actually consumed. Instead, the Boston Tea Party merely involved the destruction of tea as a protest against British taxation without representation.

One of the original chests, known as the "Robinson Half Chest," survived the original Boston Tea Party in 1773 and is on display at the Boston Tea Party Ships & Museum. It is one of the only known surviving tea chests from the event and has become a significant historical artifact.

A personal highlight of my visit was the Hollywood-style short film at the end of the tour. This award-winning documentary brings the story of the Boston Tea Party to life.

Although the entrance fee for the Boston Tea Party Ships & Museum seems quite expensive, at $36 per person, this museum is unlike any other you have ever seen. It is a must on your Boston itinerary if you enjoy state-of-the-art technology, including 3D holograms and interactive exhibits, and want to see this award-winning documentary.

Discover History and Authentic Italian Food in North End

One of Boston's oldest and most historic neighborhoods (inhabited since the 1630s), the North End is known for its rich Italian heritage and vibrant atmosphere. Often referred to as "Little Italy," the North End is famous for its narrow, cobblestone streets lined with family-owned Italian restaurants, bakeries, and cafes.

Be sure to join the hype and try some of the divine cannolis. They are typically Italian and just soooo good. The best place to find them is Mike’s Pastry. And be sure to get the pistachio and pecan caramel cannoli. Cash only.

A Sweet Mistake: The Origin of Cannoli
Legend has it that cannoli were originally created by accident in a Sicilian convent during the time of Arab rule in the region. The nuns were trying to make an Arabic dessert, but ended up making the now-famous cannoli instead. They decided to keep making these sweet treats, and the recipe spread throughout Sicily, eventually becoming a beloved Italian dessert.

North End is also home to several important historical sites, including the Paul Revere House (America’s oldest surviving residential building) and the Old North Church, where the famous "One if by land, two if by sea" signal was sent during the American Revolution.

Learn about Black Slavery at Faneuil Market Hall (aka Quincy Market)

Faneuil Hall, often referred to as "The Cradle of Liberty," is a historic marketplace and meeting place in the heart of Boston. Built in 1742, it originally served as a marketplace and gathering place for public discourse and played an important role in the events leading up to the American Revolution.

Over the years, Faneuil Hall has evolved into a vibrant marketplace known as Faneuil Hall Marketplace or Quincy Market, filled with shops, restaurants and street performers.

A Gift from a Wealthy Merchan
‍Faneuil Hall was built in 1742 as a gift to the city of Boston from wealthy merchant Peter Faneuil. Faneuil, who was a prominent merchant, financed the construction of the hall to serve as a marketplace and meeting place for the city. His contribution has made Faneuil Hall an enduring symbol of Boston's rich commercial history.

Inside Faneuil Market Hall is an informative exhibit on black slavery in the United States. In the basement is a masterfully produced 20-minute short film about what it was like to be a slave in the 1800s and how things have changed for the better. A fascinating story that will make you think. Be sure to check out the Faneuil Market Hall hours here.

Right in front of the Faneuil Market Hall you can listen to Ryan LaPerle, a folk rock, indie, pop, singer-songwriter from Boston. It's just great to hear him sing while playing guitar. You can find Ryan in front of Faneuil Market Hall every day from 5-9pm, weather permitting.

Walk the Boston Freedom Trail

The Boston Freedom Trail is a 2.5-mile historic walking route that winds through downtown Boston and takes visitors to 16 significant sites related to the American Revolution, including the Massachusetts State House, Paul Revere's House, and the Old North Church, where the famous "One if by land, two if by sea" signal was sent.

The Boston Freedom Trail is an excellent introduction to the city of Boston, where you'll not only visit iconic historical sites, but also get a feel for the vibrant, dynamic spirit of Boston. Read my guide to walking the Boston Freedom Trail on your own for an in-depth understanding of the main attractions and further helpful information.

Freedom Trail: A Walk Through History
The Boston Freedom Trail is a unique outdoor museum that was established in 1951, making it one of the first historical walking tours of its kind in the United States. The Trail was the brainchild of local journalist William Schofield, who wanted to create an easy way for visitors to explore the city's rich Revolutionary War history.

Visit the USS Constitution

The USS Constitution, also known as "Old Ironsides," is a historic warship docked at the Charlestown Navy Yard in Boston. Launched in 1797, she is the oldest commissioned naval vessel in the world. The ship forms part of the Boston Freedom Trail.

The USS Constitution earned her nickname during the War of 1812 when enemy cannonballs were seen bouncing off her sturdy wooden hull as if it were made of iron.

USS Consitution: Never Defeated in Battle
The USS Constitution is famous for never having been defeated in battle. During her service in the War of 1812, she engaged in numerous battles and emerged victorious, including significant victories over HMS Guerriere and HMS Java. These triumphs made the ship and her crew national heroes and contributed to her legendary status.

Visitors to Boston can tour this legendary ship, explore its decks, and learn about its storied past through exhibits and interactive displays. The USS Constitution remains an active duty ship, symbolizing the enduring legacy of the U.S. Navy and America's naval history. Today, it is still owned and operated by the U.S. Navy. Admission is free.

Note that it is only open Wednesday through Sunday from 10 am to 4 pm. For more information, visit the USS Constitution website.

Final Words

In a city as rich in history as Boston, there's no shortage of incredible experiences that bring the past to life. From the storied halls of the Isabella Stewart Gardner Museum to the dramatic reenactments at the Boston Tea Party Ships & Museum to the iconic sites along the Freedom Trail, Boston offers a unique blend of historic charm and modern amenities.

I hope this guide has inspired you to explore the city's best historic attractions and fill your itinerary with unforgettable activities that connect you to the roots of American independence.