5 Different Ways to Explore Boston’s Freedom Trail

October 4, 2023 | , , , ,
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Explore Boston’s Freedom Trail

Boston is full to the brim with Revolutionary History and there are sooo many different ways to experience it whether you want something immersive, full on history-packed, or just a sprinkle of history with a side of food and drinks. We’re here to make sure that your needs get met when it comes to exploring Boston’s Freedom Trail. But first, a little background on the Freedom Trail.

The Freedom Trail is a unique collection of 16 historic sites including museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond. The Freedom Trail was dedicated by Boston Mayor John B. Hynes on June 11th, 1951. Initially the trail only had 14 stops and was marked only by small signs to guide the way. Later came red paint to draw the path and finally, more permanent red brick was laid to mark the trail  in 1958. In 1972 the last two sights were added – the USS Constitution and The Bunker Hill Monument, both of which are in Charlestown. The Freedom Trail is a signature Boston experience responsible for generating over $1 billion in annual spending, and helps create jobs in hospitality, tourism, and education fields.

Now, let’s explore it!


Hop-On-Hop-Off Trolley Sightseeing Tour

Photo Credit: Old Town Trolley Tours

Old Town Trolley Tours offers a panoramic trolley tour of Boston that can be done all at once or throughout the day depending on your plans. It’s a great way to explore the Freedom Trail as well as other parts of the city without having to walk everywhere. This carefully crafted hop-on hop-off tour follows a route that takes you to all the right places to maximize your time and give you a great introduction to historic Boston. Experience the birthplace of American Independence as your expert tour conductor showcases the City with stories featuring tales of adventurers arriving in the New World and their rebellion against the British Crown.

Iconic Boston Food & History Tour

If you’re like us, you travel for the FOOD (and the history). If you are looking for an experience that feeds you both food and history then join Bites of Boston Food Tours, a local company that has been operating for over 12 years, for our Classic Bites of Boston Food Tour. As we know Boston’s Downtown is packed with Revolutionary History, but along the Freedom Trail, you’ll also find some of the best examples of the iconic dishes Boston has to offer – Lobster, Chowder, Baked Beans and Boston Cream Pie! Have you heard about these culinary classics? Curious about where to get the best of the best? Wondering why these foods became so popular in Boston in the first place? Join us on our Classic Bites of Boston Tour and you’ll learn about all of the above – and taste these iconic dishes for yourself too while also visiting five sights along the Freedom Trail. Discover downtown Boston in a different – and delicious – way!

Themed Freedom Trail Tour with Costumed Guide

Photo Credit: The Freedom Trail Foundation

Walk into history and allow a colonial costumed guide take you through the 16 stops of the Freedom Trail. Packed with history and a good amount of walking, this experience will give you the most information about the Freedom Trail if you are a true history buff and in it for allll the history. Established in 1964, the Freedom Trail Foundation was the successor to the Freedom Trail Committee, a group formed in 1958 by the Greater Boston Chamber of Commerce and the Advertising Club of Greater Boston to initially market the Freedom Trail. The Foundation was created as a non-profit organization to help promote and preserve the Freedom Trail. It has done this along with offering a variety of different tours to get out there and see it in a guided setting.

Follow the Map and Walk it on Your Own!

Photo Credit: @kimsta_travels via Instagram

If you’re more a go-at-it-on-your-own type of tourist, then download a map of The Freedom Trail and check the sights out for yourself! If you choose this option, you’re bound to get hungry along the way – we would at least – so check out our blog post that highlights some of the Classic Sights and Bites of Boston where you’ll find several Freedom Trail stops listed and a restaurant suggestion to go along with them.

Duck Boat Tour

Photo Credit: Boston Duck Tours

If you’re looking to see lots of Boston sights ranging from TD Garden where the Boston Celtics and Boston Bruins play to stops along The Freedom Trail, then Boston Duck Tours covers it all. This is a great and fun option for families with kids who need transportation and still want to see it all on both land and water!


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