Tackling the Freedom Trail in Boston

Boston Massachusetts

Boston is a city I haven’t given enough attention to over the years, and I’m not sure why that is exactly. While I may not know it as well as some other spots around the country, I was certain that it would make for a fun weekend getaway, and turns out I was right. I’m working with Marriott International to highlight some cities around the U.S. that I enjoy visiting and consider perfect for a two or three day getaway, and Boston is near the top of that list. I will soon write a comprehensive post about how best to experience Boston in just a couple of days, but today I want to highlight what I think is the city’s star experience for visitors, the Freedom Trail.

What is the Freedom Trail?

Originally organized in the 1950s, the Trail connects some of Boston’s most popular and important sites on an easy to walk pedestrian trail. 16 different locations that are integral to the history of the United States are included, while also giving visitors a chance to explore more of the city at the same time. I didn’t have a lot of time in Boston and I found that spending the morning walking the entirety of the Freedom Trail wasn’t just a nice way to see some of the country’s most important buildings and places, but to better understand the modern city of Boston as well. The Freedom Trail weaves its way from Boston Common to the Bunker Hill Monument across the river and is honestly a fun experience as well as an educational one.

Highlights of the Trail

My hotel, The Ritz-Carlton, Boston, couldn’t have been better situated to take advantage of the Freedom Trail. Located next to Boston Common, as soon as I walked out the front door I had already and unwittingly began my exploration of the Trail. Rather than describe each and every site along the walk, you can check out the official web site for that, I want to instead share those spots that I enjoyed the most and I think help best share the story of Boston and the nation.

Boston Common – Established in 1634, Boston Common is America’s oldest public park and is just as lively today as it must have been centuries ago. It’s a large, open space that wasn’t only the start of my day’s exploration, but a central spot during my stay in Boston. With my hotel room overlooking the park, I found myself there several times that day, just enjoying the sunny weather and joining hundreds of others doing the same.

Granary Burying Ground – I almost missed this spot, but I’m glad the tombstones caught my eye because it’s a fascinating place around which to meander. Established in 1660, it’s the final resting place for many notable early Americans including Paul Revere, the victims of the Boston Massacre, Samuel Adams, John Hancock and more. There’s also a monument to Benjamin Franklin who, although he is buried in Philadelphia, was actually born in Boston.

Old State House – This building in particular fascinates me because of the history it has lived through. Built in 1713, it’s the oldest surviving public building in Boston and itself a key player in early American history.

Boston Massachusetts

Faneuil Hall – The center of the tourist experience in Boston, Faneuil Hall is also the center of free speech in America since the country’s first Town Meeting was held here. Located near the waterfront, the Hall has always been a center of activity as a market and meeting place for generations. Today it’s still a marketplace, but don’t be put off by some of the crass commercialism nearby, there’s still a lot to see and appreciate here.

Old North Church – The birthplace of the American Revolution, this is the location from which the famous “One if by land, two if by sea” signal was said to have been sent, related to Paul Revere’s equally famous ride. It’s the oldest church building in the city, and still welcomes parishioners today. At the time of writing there was construction ongoing immediately in front of the church, but it’s still accessible.

USS Constitution I admit that I didn’t know a lot about this historic sailing ship before I visited, but it quickly became my favorite stop of the day. Launched in Boston in 1797, USS Constitution is the oldest commissioned warship afloat and earned her nickname “Old Ironsides” during the War of 1812 when she fought the British frigate HMS Guerriere. Part of the Naval History & Heritage Command, Navy personnel are still assigned to her today, educating the public about the Navy’s role in war and peace through tours and outreach.

massachusetts Boston

Bunker Hill Monument – No, this isn’t a copy of the Washington Monument but it’s just as interesting to visit. The Battle of Bunker Hill took place on June 17, 1775 and was the first major battle of the Revolutionary War. Construction on the monument started in 1825 to honor the battle and the importune it has in the history of the nation. Even better, visitors can walk to the top for incredible views of the city.

Where to Stay in Boston

There are plenty of incredible hotels to use as your home base while exploring Boston, including these not to miss properties.

The Ritz-Carlton, Boston

Staying at any Ritz-Carlton property around the world is always a special treat for me, but something about The Ritz-Carlton, Boston clicked with me right away. An intimate hotel located next to Boston Common, it’s the ideal spot from which to see the city. Add to that the incredible service and hospitality for which The Ritz-Carlton is so well known and you have an unbeatable hotel experience.

Boston Marriott Copley Place

Located in Boston’s Back Bay, this is an excellent spot from which to see a different side to Boston. Located near such notable attractions as Copley Square, Fenway Park and the Prudential Center, the sophisticated and thoughtful accommodations are sure to appeal to just about any type of traveler.

Sheraton Boston Hotel

Another Back Bay favorite, the Sheraton offers relaxed sophistication and friendly service and is directly connected to the Prudential Center and the Hynes Convention Center. Explore Newbury Street and Fenway Park before relaxing in their famously comfortable Sheraton Signature Sleep Experience.

Boston is one of America’s most important cities, a birthplace of our democracy and the thought-leaders who designed a system of government that has withstood the test of time. Rather than musty sites thought, the Freedom Trail brings this history to life in a way that is totally unique, while also allowing visitors the opportunity to learn more about the modern city of Boston. That’s fairly unique in my experience and is what makes the Freedom Trail in Boston a must-do for any visitor to the city.

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By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer. Also follow Matt on Twitter, Facebook and

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