Self-Guided Option Best Bet for Touring Boston’s Freedom Trail

It’s October, the prime time to visit New England for fall foliage leaf-peeping.

If your visit takes you through Boston, there are dozens of amazing sites to experience. At the top of my list is the Freedom Trail. The 2.5-milelong path through downtown Boston passes by 16 significant American sites. Mainly marked with a red brick trail embedded into the sidewalks and streets, it winds between Boston Common to the Bunker Hill Monument in Charlestown.

Many first-time visitors wonder precisely how to “do” the Freedom Trail. 

Here are my recommendations:

Yes, the Freedom Trail is 2.5 miles long, strictly speaking, but there are many sites 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 7 miles of walking over six hours.

Some points are steeply uphill, and some are downhill, depending on where you begin. There are stairs. This would make an arduous undertaking for anyone not in decent physical shape.

If you begin the Freedom Trail at the Bunker Hill Monument in Charlestown, you will embark from a high point, cross the Charles River into the North End of Boston, and continue where almost all the other sites along the trail can be found.  

There’s a great Visitor Center, where you can get an overview of the Battle of Bunker Hill and use the restroom before you head out.

Alternatively, you can begin the trail on the Boston Common. The historical sites from this starting point come quickly and frequently.  

What about a formal tour group?  May I be honest with you?  I HATE group tours. I loathe them.  I don’t like walking amidst a big group of people. I don’t like being subject to the speed of a group.  

There are dozens of apps you can download on your phone, allowing for a self-paced walk with information about the sites along the way.  

While walking the trail, if you can go inside a site, do it.  You will pay for a ticket, but I believe, if you are going to do a thing, then do it thoroughly.  Go inside Paul Revere’s Home.  Go inside the Old North Church.  See it all.

A few other tips: 

The Freedom Trail takes you through the heart of the North End, a predominantly Italian neighborhood with dozens of great restaurants, coffee shops, and bakeries.

A must-eat while in Boston:  a Boston Creme Pie.  Obviously.

Mike’s Pastry Shop is the go-to spot in the North End.  Pick from a dozen flavors of cannolis, cookies, and cupcakes in addition to fantastic Boston Creme Pie by the slice.  

I have no recommendations for Boston Baked Beans.  You’re on your own, there.

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

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Mary The Curious Cowgirl Meier-Evans

Mary Meier-Evans, of University Park, has a Texas-sized curiosity which keeps her longing to see new sites both near and far – though road trips, rather than international flights, make the most sense to her in 2020. Check out her blog and podcast at

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