The Freedom Trail in Boston, Massachusetts | Tips & Tricks

More than four million people set foot on the Freedom Trail every year to see some of Boston’s most famous historic sites. This 2.5-mile trail passes by 16 significant landmarks, a journey made relatively foolproof by the red paint/red brick line leading the way. Ready to lace up your walking shoes and join in? Here are our tips and tricks for enjoying your time on the fabled Freedom Trail.

The Freedom Trail in Boston, Massachusetts | Tips & Tricks

Like many children who grew up relatively close to Boston, I was herded by some valorous teachers along that revolutionary red stripe during a school field trip. And honestly? I can’t remember a bit of it. But many years later, I approached the trail for a reprise. As a Massachusetts resident, I found the idea of becoming a tourist in my own state charming. And after the fact, I stand by the statement that — whether you’re a Boston resident or a visitor from thousands of miles away — the Freedom Trail will entertain. Yes, you might get tired and end up saving the last mile for another day. Yes, a granola bar will come in handy. Yes, there are many Starbucks locations on the trail (three, to be exact). And yes, you’re going to want to wear comfortable shoes.

1. Where does the Freedom Trail start?

The trail begins at Boston Common, the oldest public park in the United States.

2. Where does the Freedom Trail end?

It winds up at the Battle of Bunker Hill Monument in Charlestown.

3. How should someone prepare to walk the Freedom Trail?

We recommend visiting the Freedom Trail Foundation’s website and printing its handy PDF map of both the Freedom Trail and the Black Heritage Trail. The latter is in Beacon Hill, near the Freedom Trail’s starting point, which means that an ambitious sightseer could easily walk them back-to-back (though this may mean walking one in reverse, which is what I did). You can read about the Black Heritage Trail here.

4. How long does it take to walk the Freedom Trail?

It depends on whether you stop for food or drink, take a shopping break at Faneuil Hall, or enter into any of the historic buildings along the way. The path winds from downtown through the North End and into Charlestown for a grand total of 2.5 miles. You can read about the accessibility of the route here. According to the Freedom Trail website, which offers many potential itineraries, most walking tours last between 60 and 90 minutes. It took me about two hours, including many photo ops and one cannoli stop.

5. Is it better to take a guided tour or just wing it?

I personally enjoyed the freedom of walking the trail on my own. That said, the tour guides are knowledgeable — and very chipper (you can decide whether that’s a pro or a con). Which brings us to…

6. What’s up with the people in costumes?

Those are the tour guides! To read about the many tours offered by the Freedom Trail Foundation, visit the website. (FYI: If you’re wondering what it takes to become a Freedom Trail guide, we answered that question in our May/June 2011 issue.)

7. What are the stops on the Freedom Trail?

1. Boston Common
2. Massachusetts State House
3. Park Street Church
4. Granary Burying Ground
5. Kings Chapel
6. Ben Franklin Statue/Boston Latin School
7. Old Corner Bookstore
8. Old South Meeting House
9. Old State House
10. Boston Massacre Site
11. Faneuil Hall/Quincy Market
12. Paul Revere’s House
13. Old North Church
14. Copp’s Hill Burying Ground
15. USS Constitution
16. Battle of Bunker Hill Monument

8. Where are the best places to eat on the Freedom Trail?

Here are some recommendations from us here at Yankee: Where to get the best lobster roll on the Freedom Trail: Head for Neptune Oyster on Salem Street in the North End, or Luke’s Lobster in Downtown Crossing. That said, if you want to get our food editor’s favorite lobster roll in the city, head over to Row 34 on Congress Street. Where to get the best cannoli on the Freedom Trail:  Yankee senior food editor Amy Traverso has declared that in the North End, “almost any take on cannoli is a good bet.” She recently reviewed four of the North End’s top bakeries to see which had the best cannoli; alas, the shop she gave first place to, Maria’s, has announced it will be closing. So as the path winds toward Paul Revere’s house, look for her second pick, Modern Pastry Shop. As for me, I stopped by Bova’s Bakery, whose cannoli Traverso dubbed “by far the prettiest of the lot.” It did not disappoint!

Where to eat at the beginning of the Freedom Trail: JM Curley serves playful comfort food, including fried pickles, duck poutine, and barbecue pork mac ’n’ cheese. Fill up on fried goodness —  then walk it off over the next 2.5 miles. Where to eat in the middle of the Freedom Trail: Faneuil Hall Marketplace or Boston Public Market — with all their food carts, kiosks, and restaurants combined, these two spots offer just about anything you can imagine. Where to eat at the end of the Freedom Trail: Only a six-minute walk from the end of the trail, the Brewer’s Fork in Charlestown sports an impressive array of brews and excellent wood-fired fare, plus an outdoor beer garden that’s perfect on a warm-weather day. For more tips, see our guide to the best places to eat in Boston.

9. Any tips for a unique Freedom Trail experience?

For your first time walking the route, you may want to stick to tradition. That said, here are some ideas for spicing up a Freedom Trail trek:

• Celebrate liberation with libation on an organized Freedom Trail Pub Crawl, or go the DIY route and pinpoint some watering holes to visit along the way.
• Work up a sweat on an early morning Freedom Trail run — perfect if you’re traveling with some late sleepers who perhaps don’t share your enthusiasm for the Revolution.
• Start at Bunker Hill and walk the trail backward. (This may not be your definition of thrilling, but then again, it may.)
• Take a trolley tour or a duck boat tour, which both cover much of the same territory as the Freedom Trail.

Scenes from the Freedom Trail

Do you have any tips for how to have a great experience on the Freedom Trail?

SEE MORE: Inside the Old North Church in Boston 75 Things Every New Englander Should Do Beacon Hill, Boston | Exploring Boston’s Most Famous Historic Neighborhood

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