Boston’s Freedom Trail and the Great Cannoli Showdown
Let’s start at the very beginning. (A very good place to start, as a certain singing nun once told us.) Your two gay grandpas headed to Boston, Massachusetts, to walk the Freedom Trail, soak up a whole lot of American history, and settle one of the city’s great debates once and for all: who makes the best cannoli in Boston?
Following the Red Brick Road
Dorothy followed the yellow brick road. We followed the red one. The Freedom Trail is a line of red brick (and paint) set into the sidewalk, winding about 2.5 miles (4 km) through downtown Boston and connecting 16 official historic sites.
We started our day at the visitor center on Boston Common, where you can pick up a map of the whole trail. Then we set off to see how long our feet would hold out.
State House, Park Street Church and a Cemetery Full of Patriots
First stop: the Massachusetts State House with its golden dome. Just down the street is Park Street Church, founded in 1809, which played a big role in the movement to abolish slavery in the United States.
A lot of people think cemeteries are spooky, but the Granary Burying Ground turned out to be one of our favorite history lessons of the day. Paul Revere, the silversmith of midnight-ride fame, is here. So are John Hancock and Robert Treat Paine, two Massachusetts signers of the Declaration of Independence. And so is Samuel Adams, who, no, did not brew beer, and no, did not star in Hamilton, but did help lead a revolution. There’s even a family monument for Benjamin Franklin’s parents. (Ben himself is buried in Philadelphia.)
A Revere Bell, the First Public School and a Very Political Donkey
Quiz time, Grandpa: what’s famous about King’s Chapel? The bell in the steeple was recast by Paul Revere’s foundry, and it’s the largest bell they ever made. It still rings today.
Next up was a spot many schoolchildren might curse: the site of the very first public school in America, founded in 1635. It’s marked with a statue of Benjamin Franklin. Nearby, a bronze donkey reminds us that donkeys played an important part in forming our government. Elephants, not so much.
And are we the only ones who think the Old Corner Bookstore looks suspiciously like a fast-food restaurant?
Where the Revolution Got Loud
We’ve all heard of the Boston Tea Party. Old South Meeting House is where about 5,000 colonists gathered on December 16, 1773, before heading down to the docks. Kind of an early Christmas present for good old King George.
The Old State House is one of Boston’s most famous buildings, and the Declaration of Independence was read to the crowd from its balcony in 1776. Just outside, a marker shows the site of the Boston Massacre, where British soldiers fired into a crowd in 1770 and five colonists were killed.
Then came Faneuil Hall, where Sam Adams and other patriots gave fiery speeches for liberty. And how convenient: there’s a Sam Adams taproom right there. After a couple of beers, we decided to get lost wandering the streets of Boston. Well, maybe not intentionally.
A Little Intermission (Seven Weeks Long)
Here’s where our Boston trip took a detour. Boston reminded us so much of London (there’s always a pub nearby) that we interrupted things for a seven-week road trip through the United Kingdom. Then it was back to Boston to finish what we started, starting with a boat ride in the harbor. One if by land, two if by sea, and this time we were doing a two. Boston is a beautiful city to see both from land and from the water.
Paul Revere, the Old North Church and Bunker Hill
Day two started with breakfast at the Beantown Pub and a glass of orange juice for a little vitamin C. (It’s just orange juice. There’s no vodka. Not yet.) Then we picked the trail back up at the house of hometown hero Paul Revere. Built around 1680, it’s the oldest house still standing in downtown Boston, and it’s where Revere set out on his famous midnight ride in 1775.
Around the corner is the Old North Church, the oldest standing church building in Boston. It’s famous for the lanterns hung in its steeple (“one if by land, two if by sea”) to tell the patriots how the British were coming.
Our trail ends at Bunker Hill, where the battle was fought on June 17, 1775. It’s where we get the famous order, “Don’t fire until you see the whites of their eyes.” The monument that marks the battle stands 221 feet tall.
Full disclosure, folks: we only made it to 14 of the 16 sites. Why? Because one of us is an architect, so we had to go see all the pretty buildings!
Beacon Hill, Acorn Street and the North End
There was no way Grandpa Bobby was coming to Boston without seeing Beacon Hill: cobblestone streets, brick row houses and gas lamps. The great thing about Boston is that it’s a living city, not a museum. People live here, shop here and eat out here.
Acorn Street is one of the most photographed streets in the country, a car-free cobblestone lane straight out of history. We asked an elderly gentleman who lives there whether he minds all the tourists. He said he loves seeing people enjoy his historic neighborhood.
Over in the North End, Boston’s Little Italy, the streets were still decorated from the Saint Anthony’s Feast, held every year in late August. No, those aren’t early Christmas decorations. The North End is lively and fun, and you’ve got to go.
And while Grandpa Bobby goes in for all things architecture, Grandpa Scott goes in for all things shopping, which means Quincy Market, an iconic food market since 1826.
The Great Cannoli Showdown
Now, what you’ve all been waiting for: Modern Pastry vs. Mike’s Pastry, two famous North End bakeries just a short walk apart on Hanover Street. Who makes the best cannoli in Boston? We had to find out for ourselves. Same order at both shops so it was apples to apples: a traditional shell with ricotta filling, chocolate chip for Grandpa Bobby and pistachio for Grandpa Scott.
Round one: Modern Pastry. Who knew Paul Revere picked such a good neighborhood? Modern is right around the corner from his house, and they fill your cannoli right there while you wait. Crispy shell, creamy ricotta, and not too sweet. Grandpa Bobby said it tasted just like he remembered from when he was a kid. Grandpa Scott said it was right up there with the ones we had in Sicily, which were the best we’ve ever had. It earned four yummers, with the fifth held back in case something better came along.
Round two: Mike’s Pastry. Before we even took a bite, the experience wasn’t as warm. There was no seating, and the service was brisk and a little businesslike (maybe from serving so many tourists). The cannoli was still yummy, with a shell just as crispy. But Grandpa Bobby found Modern’s filling a little creamier, and Grandpa Scott found Mike’s a little grainy.
And the Winner Is…
The Great Cannoli Challenge of 2024 goes to Modern Pastry, founded in 1930 on Hanover Street. It won on taste, and it won on feel too: at Modern, we felt welcome.
Modern Pastry: Creamier filling, crispy shell, fills to order, warm welcome. 4 yummers. Winner.
Mike’s Pastry: Crispy shell, filling a little grainy for us, no seating, brisk service. A close second on taste.
Have you walked the Freedom Trail? And are you Team Modern or Team Mike’s? Tell us in the comments, we read every one!
Watch the full Boston video on our YouTube channel and walk the Freedom Trail with us, cannoli and all. If you enjoy traveling with us, please subscribe, give the video a like, and let us know in the comments where we should go next.
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Travel Your Heart,
Grandpa Bobby &
Grandpa Scott
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