The Boston Freedom Trail Walking Tour

As a lover of bargains, history, and little old men in uniforms, I can safely say that one of my favorite things about travel is partaking in the many free national park tours our country has to offer. America’s National Park Service seems to exclusively hire flirty male septuagenarians as guides, and I am completely okay with that. (Interestingly, docents at museums in the U.S. are almost exclusively spunky single women in their golden years. I smell the makings of a senior citizen rom-com staring Susan Sarandon and Ed Asner. YOU’RE WELCOME, HOLLYWOOD.)

My love for gray-haired men in uniform is so strong that it sincerely saddens me to tell you that the NPS guided tour of Freedom Trail in Boston is not really worth the time. At least, not from a historical perspective. It was educational and informative, though, when it came to pastries.

And while I am sure you’d rather I discuss baked goods first, you will have to wait, as I did, and suffer through all the boring stuff. I know. Life is difficult.

The Freedom Trail tour begins at 15 State Street near the Old South Meeting House (the times of the tour vary depending on the year. For the full list of hours, see here). It’s supposed to take 90 minutes, but mine clocked in at over two hours, which is an exceptionally long time to stand in the cold while not eating sweets. I had tried to take the tour on numerous prior trips to Boston, and always managed to miss it. Each time I did, I built it up more and more in my mind, until at the very end, I had convinced myself that the Freedom Trail tour included live re-enactments by costumed actors and bottomless cups of cocoa.

Sadly, none of that was true. It did have this gentleman, though, who was adorable, but not terribly good at projecting his voice.

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His accent was fantastic. It was one part Shelbyvillian, one part old Maine fisherman. He personally described it as an “Old Yankee” accent, and I could picture him wearing overalls and taking about a nor’easter. Unfortunately, he spoke so softly it was difficult to hear him, and the roaring wind that wound up the narrow streets of downtown did not help. We clustered around him, and one woman asked him if he could speak up.

“Well-uh, no. ‘Fraid I can’t-uh talk loudah than this.”

He explained to us that the tour generally made only one indoor stop in Faneuil Hall, but since it was currently closed for renovations, the entire tour would be outside, in the unseasonably cold May weather. We walked by the Old State House, the Old South Meeting House, and Paul Revere’s house. Fortunately, I had visited these places on my own time in previous trips – otherwise I’d have felt a bit let down by the tour (“Let’s walk past all these historic sites, but not go inside a single one! FROSTBITE BUILDS CHARACTER!”)

Paul Revere's house, where he impregnated his wife with A LOT of babies.

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It didn’t help that our guide wasn’t exactly … urgent, shall we say? 90 minutes is long enough to dedicate to a walking tour, but 2 hours is excruciating, especially when you can’t really hear what’s going on over the chatter of your own teeth. I suspect that had I gone on a warm spring day, my experience would have been radically different (in fact, I may go again if I am in Boston on a warmer day).

Oh, and did I mention I managed to snag myself a nemesis sometime during the course of the tour? I seem to have a talent for pissing people off. Not really sure how it happened (that’s a lie. I know exactly how it happened. I asked the tour guide where he was from, and he explained that his usual reply is “Up north. Not from around here.” I said that I figured he wasn’t from Boston, because it didn’t really sound like it, and one woman pounced on me. “We don’t all sound like that,” she growled, angrily. And I tried to furiously apologize, because she resembled a young Chris Farley, and could have seriously messed me up). For the rest of the tour, she glared at me.

So, let’s recap my experience thus far:

• We were collectively freezing.
• It was raining. Did I mention that? It was.
• A woman who bore a striking resemblance to one of my favorite deceased corpulent comedians looked like she was going to give me a smackdown.
• There was no hot cocoa.
• IT LASTED TWO HOURS.

And then, blissfully, it ended. I stood, shell-shocked. Was it really over? Yes. Everyone had begun going their separate ways (even my nemesis had scampered off, but not before shooting me one last final glare). A few resilient souls lingered around, asking the tour guide questions. It all merged into white noise. I had apparently fallen asleep while standing in the middle of Paul Revere Mall.

“Can you tell me how to get to Modern Pastry?” someone asked.

My head snapped up. I was suddenly wide awake. What was that about a pastry?

The tour guide chuckled.

“Used ta be, everyone asked ’bout Mike’s Pastry. But-uh folks in the know, they’re uh askin ’bout Modern Pastry.”

I didn’t hear what he said next. I was already running down the street, tongue flapping in the wind like a giddy golden retriever. I stopped when I saw this:

The promised land.

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The Jews spent 40 years roaming the desert. I spent two hours roaming Boston without dessert. And now I had reached it. I had visited Mike’s pastry in the past and deemed it good, but Modern was superior. They had all the Italian pastries and cookies that I remembered from my east coast childhood: little sandwich cookies shaped like leaves, tiny nut shortbreads rolled in powdered sugar (that made you resemble a cocaine addict after eating them), three-layered little cakes which are supposed to look like the Italian flag but don’t really.

I will not tell you how many of these I ate. But "all of them" would be a good guess.

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And cannoli. Itsy-bitsy filled-to-order cannoli in flavors both traditional and not. Since Modern Pastry only accepts cash, I only got two of the little buggers. Otherwise, I’d have downed a half dozen and not thought twice about it.

These I actually shared with Rand: ricotta and chocolate cream filled cannoli.

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Later, from the warmth of my hotel room, I ate chocolate-enrobed torrone and tried to sum up what I had learned on my National Park Tour:

• The black circle on the pavement outside the Old State House is where the Boston Massacre happened. I knew it was around there, but didn’t realize that circle marks the exact spot. According to our guide, they’ll be adding a more fitting memorial there soon.
• The large lion and unicorn on top of the Old State House are symbols of the British monarchy. There were torn down and burned during the revolution, and replaced years later, amidst some controversy.
• Modern Pastry is pretty darn good. Most of the cookies are Americanized (it’s authentically Italian in the sense that they only take cash, and little old Neapolitan women will cut in front of you in line). Get cannoli and hazelnut torrone.
• That’s pretty much it.

Would I recommend my experience to someone else? The part with the cookies, yes.

As for the National Park Tour, you can skip it unless the weather is great and you don’t mind killing some time. A guidebook will serve you just as well, and you’ll be able to enter all the places we only saw from the outside.

Regardless of what you do, be sure to finish it with a cannolo. It’s what the patriots would have done, had they an Italian bakery close by.

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The Essentials on the Boston Freedom Trail Guided Tour (by the National Park Service):

• Verdict: Meh. It’s a good overview, but not really great. (I’d just get a guidebook and go on your lonesome).
• How to Get There: Take the T to State Street.
• Ideal for: History buffs; folks impervious to the cold; anyone who really likes to walk.
• Insider Tips: The tours fill up fast, and they’re first-come, first-served. Arrive at least half an hour early to pick up your sticker and reserve your place on the tour. Wear incredibly comfortable shoes and be ready to walk. You won’t be able to enter most of the buildings on the tour, so plan to visit them again later. (I recommend going inside Paul Revere’s House and the Old South.)
• Nearby Food: I’ve covered you on the pastry front, but if you are looking for something savory, there are lots of options for good Italian food in the North End. Grab a bite when the tour is over. (Or stop by Quincy Market if you want something before the tour.)
• Good for Kids: No. A thousand times no. I’m 30 and I was bored.