10 Best History Tours In Boston, Massachusetts - Updated 2024

Melanie
Contributing Writer
Updated
| 4 min read

Boston is one of the oldest cities in the US. Its history can be traced back to the 1600s, when European colonists occupied the area, leading to the deaths of about half of the Native American population due to smallpox. The most memorable part of its history is, without a doubt, the Boston Tea Party, an event which many say gave birth to the American Revolution but which also led to the economic, cultural, and commercial decline in the city and took decades to rebuild. However, it again found itself in the middle of the struggle when it was used as the base for anti-slavery activities during the Civil War. These are only some of the key historic events that happened in the area. Join the best history tours in Boston, Massachusetts, to get yourself acquainted with the city’s history.

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1. Learn about the history beyond the Freedom Trail

Many visitors who want to acquaint themselves with Boston’s history usually head to Freedom Trail. While that already gives snapshots of what the city went through, it misses out on some other important stories. This tour is intended to fill in at least some of the gaps and give guests more information that even history books don’t cover. Among the stops included in the tour are the Long Wharf, the Rose Kennedy Greenway, the Custom House Tower, the Old State House, King’s Chapel, the Massachusetts State House, Quincy Market, and Beacon Hill.

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2. Meet the spooks and serial killers of Boston

Did you know that the Victorian-era of England reached Boston? And that a number of mysteries - from the supernatural to the criminal - emerged during this era? By joining this tour, you will get to know some of these, particularly those experienced in Boston’s South end, the oldest neighborhood in the city. Not only will you get to learn more about the serial killers and other criminals that prowled the streets during that time, you will also find out about unexplained phenomena, and even get to hear about the first person in America to be accused as a vampire.

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3. Learn about Boston's rock'n'roll past

Did you know that Boston played a key role in shaping the lives and careers of the legends of rock and roll, including Bob Dylan, Bruce Springsteen, Nirvana, Radiohead, and Van Morrison, among others? This activity will walk you through their stories and give you insights into how the city influenced rock and roll and other music genres, such as blues, and folk. This tour should not be missed by rock lovers.

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4. Explore the dark side of Boston

This activity will take you to explore the dark side of Boston, literally and figuratively. The night tour, which runs for about 90 minutes, brings guests deep into the stories about some of the shadiest characters of the city, including the Boston Strangler, Whitey Bulger, and the Mafia. Be sure to wear comfortable shoes, as this tour will require a lot of walking.

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Boston Tour Guide

Naim Benmayor

Naim Benmayor

As a Boston tour guide, I have the added experience of being a world traveler. For many years, I frequently visited Europe, Asia, and Latin America on business. During this time, I also organized tours of the USA, Europe and Asia for my business clients. I now bring this passion, excitement and expertise to the Boston area.By exploring the globe, I was exposed to various cultures, and this uniq... Read more

5. Hike the Boston Harbor islands

This activity is a nature hike and a historical tour rolled into one. The tour starts from Long Wharf, where the host and his guests take the ferry to Spectacle Island. During the 4 km (2 mi) trek, the host will share not just stories about the history of the islands, but also bring guests to the highest point of the islands so guests can enjoy views of the harbor and downtown Boston.

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6. Meet the key figures from the American Revolution

Talking about history tends to put some people to sleep. With this tour, you can be sure that you will remain awake throughout the entire time. The activity will bring the Freedom Trail to life by introducing you to the key figures of the American Revolution, including John Hancock, Sam Adams, John Adams, Paul Revere, Joseph Warren, and James Otis. Interspersed in the discussions on history are facts about the present, including a trip to bake shop, one of Boston’s best-kept secrets.

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7. Uncover the lost stories of American Revolution

A discussion on the American Revolution tends to focus on the chains of events and dates. This activity aims to fill in the gaps and shares the untold stories of the motivations and mindsets of the key personalities driving the revolution. Dive into their psyches even as you visit the key historical landmarks in the city, via the streets of the original neighborhoods.

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8. Scare yourself with a ghost tour

If you love a good scare, sign up for this tour. This activity lets guests experience the creepiest and spookier side of Boston. A 17th-century gravedigger brings you to the haunted places in the city, including ancient burying grounds. You’ll get to learn about the key figures in Boston’s history as well as get to visit the graves of some of them.

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9. Go beyond Boston

There are other fascinating places just outside Boston, and this tour takes you to some of them. The first stop is Quincy, which was the birthplace of two men who would become president of the country. Next on the list is Plymouth, where you can find a 400-year-old harbor. Other stops here are Plymouth Rock and Plymouth Plantation. The last stop on the list is Mayflower II, where you will get the opportunity to learn more about the lives of Pilgrims who made Massachusetts their home.

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10. Dive into real-crime stories of Little Italy

Fans of crime shows will get a kick out of this activity. This walking tour takes guests around North End, where they will get to see and learn about the villains of Boston’s history who committed some of their crimes here. One figure is related to the Boston Massacre, while another is a woman who was accused as a witch. You’ll also get to learn about the anarchists who were active from the 1800s all the way to the 1900s.

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Have a better appreciation of American history during your Boston visit

Boston is one of the oldest cities in the country and holds a special place in the annals of history of USA. If you want to have a deeper appreciation of the city’s and the country’s past, book at least one of these tours and find out how the events of yesteryear continue to influence what is happening today.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Melanie is a freelance travel writer. She considers freelancing for Trip 101 to be a combination of two of the things she loves: writing and traveling. She has gone sightseeing with family,...Read more

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