Many first-time visitors to Boston wonder how to follow the Freedom Trail.  Where does the Freedom Trail Start?  What is the best Freedom Trail Walking Tour?  These are all questions I have asked myself, Googled for the answers, and ultimately, after a few visits to Boston, have found solid answers.  Here are my recommendations.


How to Follow the Freedom Trail


Probably the most popular thing to do in Boston is to enjoy experiencing American History by walking the Freedom Trail.  What exactly IS the Freedom Trail?

The Freedom Trail is a 2.5-mile-long path through downtown Boston, Massachusetts, that passes by 16 locations significant to the history of the United States. Marked largely with a red brick trail embedded into the sidewalks and streets, it winds between Boston Common to the Bunker Hill Monument in Charlestown.

According to The Freedom Trail.org web site, “the trail was preserved and dedicated by the citizens of Boston in 1951, the Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.  Today the Freedom Trail is a world-renowned, signature tourist experience attracting over 4 million people annually to visit Boston’s precious sites.”

Much of the trail is in the very busy downtown city center.  So expect skyscrapers, hotels, busses, and lots of people simply walking to work, or going about their normal lives.


Old State House Boston

Old State House, Boston



Where Does the Freedom Trail Start


It you want to see ALL the sites on the Freedom Trail, there are two places to start.

But let me ask you to consider a few important details, first.

  • Yes, the Freedom Trail is 2.5 miles long, strictly speaking, but there are many places you will want to walk through, around, etc.  And, you might make a detour here and there for shopping or eating.  In July 2021, I walked the entire Freedom Trail with my husband and daughter.  We each recorded almost seven miles of walking over a six hour time period.
  • There are points that are steeply uphill, and points that are downhill, depending on where you begin.  There are stairs.  This would be a VERY hard undertaking for anyone who is not in decent physical shape.
  • The number of other tourists on the Freedom Trail can make your progress slower, or faster.  Obviously summer months are high-tourist times.



Two pair of feet standing on a Freedom Trail Marker

One of two starting points along The Freedom Trail



So, let me give you my pros and cons for the two starting points.


If you start at the Bunker Hill Monument

  • PRO: You will begin your walk from a very high hill, and then work your way down, before crossing the Charles River into the North End where almost all the other sites along the trail can be found.  There’s a great Visitor Center there, where you can get an overview of the Battle of Bunker Hill, and use the restroom before you head out.
  • CON:  It’s a pretty decent walk from Bunker Hill to the next site along the trail, so impatient tourists, or tourists who tire easily could feel discouraged before reaching the next site.


If you start on the Boston Common

  • PRO:  You will begin your walk at Ground Zero of most of the historic sites.  There’s a Visitor’s Center where you can use the restroom, and then begin your journey.  The sites from this starting point come quickly and frequently.  You could certainly see 99% of the Freedom Trail, and then cross the river to see Bunker Hill….or not.  Depending on how tired you are.
  • CON:  MOST tourists start here, so you can expect herds of people, especially during the summer months.  If you are an impatient tourist, this might feel discouraging right at the beginning of your walk.


What is the Best Freedom Trail Walking Tour


May I be honest with you?  I HATE group tours.  Like….I loathe them.  I don’t like walking amidst a big group of people.  I don’t like being subject to the speed of the group.  I don’t like listening to people complain….or ask dumb questions.  And yes, even though teachers typically say there are no dumb questions, I’ve heard people ask some REALLY dumb questions.

And I’ve asked my fair share of dumb questions in my life, I can assure you.  That’s why I love Google.  Pro Tip.

And I don’t want to be grumpy, because I really love history and historical sites.

So, I was delighted when my daughter and husband found a very good App for walking the Freedom Trail.  I believe it was about $7, and was completely self-paced.  We all popped in our ear buds, and walked the trail at our own pace.  Speeding up, or slowing down as The Spirit moved us.

This app provided the down-and-dirty basic information about each site.  But, some sites also included additional information, if you wanted to go deeper.  I love that option!

I am sure there are good group tours.  I just can’t personally recommend one.  But, if you have participated in a good group tour, feel free to share your experience in the comments!


Freedom Trail App Icon

The Freedom Trail App Icon we used in 2021.



a bronze state with a church in the background

The Bronze Paul Revere Memorial Statue with the spire of the Old North Church in the background.



Other Freedom Trail Tips


  • The Freedom Trail will take you smack-dab through the heart of the North End, a largely Italian neighborhood, with dozens of great restaurants, coffee shops, and bakeries.
  • Two restaurant recommendations:  Mamma Maria is directly across the street from Paul Revere’s Home.  It’s FABULOUS!  Leaning a little more toward fine-dining, we enjoyed an amazing dinner here. Neptune Oyster Bar is a very well-known eatery, famous for its Lobster Rolls.  They do not take reservations, so be prepared to wait in line.
  • A must-eat while in Boston is:  a Boston Creme Pie.  Obviously.  Mike’s Pastry Shop is the go-to spot in the North End.  Again, always a long line, but it typically moves fast.  And, there’s a dozen flavors of cannolis, cookies, and cupcakes to choose from, in addition to fantastic Boston Creme Pie by the slice.
  • I have no recommendations for Boston Baked Beans.  You’re on your own, there.
  • While walking the trail, if you can go inside a site, do it!  You will pay for a ticket, but I’m of the opinion, if you are going to do a thing…then do the thing completely!  Go inside Paul Revere’s Home!  Go inside the Old North Church.  See it all!
  • Be weather aware!  Weather can roll in quickly, and it’s no fun to be on a long walking tour if you are too hot, too cold, too wet, or too whatever.
  • Look up!  Those red trail bricks become strangely mesmerizing.  Like, somehow, if you take your eyes off the sidewalk, you will be irretrievably lost off the trail.  Not to worry,  You won’t.  And if you don’t look up, you will miss all the amazing neighborhoods you will walk through.  You will miss looking around and thinking about what Boston must have felt like for Paul Revere.  You will miss seeing very historic parts of Boston!


Now.  Fire up the John Philip Sousa, and get knee deep in American History, y’all!


Bio about Mary Meier Evans The Curious Cowgirl



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