Boston is one of the United States’ most patriotic cities for one simple fact: It’s where historic moments were formed.
Videos by TravelAwaits
Similar to significant historic cities like Philadelphia and smaller standouts like Savannah and Virginia Beach, Boston has played a critical role in shaping our nation. It was the birthplace of important American figures, the location where democratic ideas were formed, and is home to dozens of National Historic Landmarks—a grand total of 57, if you like to count.
In short, there are layers in American history to uncover in Boston. And while the city has a fantastic (and free) Historic Freedom Trail, that’s just the tip of the iceberg. If you want to dive deep, you need history tours in Boston that focus on events, eras, and architecture. Don’t worry—some are also pub crawls.
Whether or not you think you like learning about the past, here’s where to find the best history tours in Boston.
History tours in Boston: Freedom Trail walking tours
- Freedom Trail History Small Group Tour: Dive deep into the Freedom Trail as your guide covers the tumultuous period between 1760 and 1775, when circumstances that caused the Revolutionary War to mount. You’ll get to see all 16 official Freedom Trail sites on this popular tour.
- Freedom Trail Tour with Costumed Guide: If I could give you one tip on history tours in Boston, it would be to look for costumed variations. This Freedom Trail walking tour comes with a guide wearing a historically accurate costume. Just know that in exchange for fanfare, you won’t see all 16 Freedom Trail sites.
- Freedom Trail Experience: Speaking of costumed guides… if you like the idea, check out this Freedom Trail experience. It comes with very passionate guides who are dressed to the nines… 1700s-style. Based on the reviews, it looks like just about every visitor was obsessed with their costumed guide.
History tours in Boston: other walking tours (plus, cycling)
- Freedom Trail, Beacon Hill, & Back Bay Walking Tour: Experience the Freedom Trail, along with historic points in Beacon Hill and Back Bay. You’ll feel like you’re traveling back in time as you learn about the city’s historic underbelly.
- Underground Railroad History in Beacon Hill: Forget the Revolutionary War for a second. This tour focuses on Civil War-era Boston and how the city’s Beacon Hill area served as a hub for the Underground Railroad.
- Boston Architecture & History Walking Tour: This small group tour includes a deep dive into three of Boston’s most well-known attractions, including Copley Square, Boston Public Garden, and Beacon Hill. Your focus is on history—as well as the famous architecture that emerged from Boston’s historic era.
- Cycling History & Landmarks Tour: Set out in Boston’s historic North End neighborhood, then head down toward Copley Square and Fenway Park. While you pedal, you’ll stop to learn about major landmarks and neighborhoods.
- Immersive e-Bike History Tour: If cycling is a little too demanding, take this e-bike tour. You’ll glide through over 400 years of Boston history, as the listing says. The tour also takes you through eight of Boston’s most iconic neighborhoods, giving you a lay of the land.
History tours in Boston: with food and/or booze
- A Taste of the Freedom Trail: This small group travels along the Freedom Trail while heading to restaurants that locals love. You’ll get to learn about history while you taste the city’s most iconic eats, from Boston cream pie to lobster rolls.
- Guided Seafood Tasting & History Tour: Speaking of lobster rolls, this tour dives deep (get it?) into Boston’s seafood tastes. You’ll get to explore fishing piers, mini-restaurants, and more as you sample dishes like chowder, lobster rolls, and more. Along the way, you’ll learn about Boston’s maritime history and penchant for seafood.
- North End Flavors & Freedom Trail Tour: Explore the North End neighborhood and the Freedom Trail as you learn about history from a passionate guide and sample beloved eats. Consider it a great way to convince any non-history-lovers who are foodies to go on a historic tour.
- Freedom Trail History Tour Pub Crawl: If you’d rather drink your way through Boston’s Freedom Trail, you’ve got options. This small-group pub crawl includes stops at popular pubs, local haunts, and dive bars that you might not find otherwise.
- Revolutionary & Drunken Past Bar Crawl: Between Freedom Trail stops, you’ll head into beloved taverns—some of which are centuries old. Just know that this tour has an even balance of history to ‘frothy brews’, as the host puts it. You’ll see ten of the Freedom Trail’s 16 stops along the way.
- 2-Hour Historic Pub Crawl: If you prefer small groups and the chance to socialize with fellow travelers, this two-hour pub crawl is for you. It includes plenty of commentary on history and popular sites—most of which take place inside historic pubs and taverns.
