Freedom Trail Food

I’m kind of a history person, so I was excited to walk the Freedom Trail in Boston. My friend and I dubbed ourselves as “Freedom-ers” and set off along the painted red line from the Boston Commons. (We went backwards, by the way. I think you are supposed to start in Charlestown). We were ready for museums, Paul Revere’s House, and Bunker Hill.

We had barely passed our first historic cemetery when we stepped onto School Street and our conversation turned to food. At 60 School street sits the Omni Parker House Hotel, historic site of the first Boston Cream Pie. The glamour shots of the dessert in the window did look tempting, but we decided to keep our distance. We had planned a full-on touristy day are were dressed for the part. We did not want to stroll into the fancy hotel in our get-up of walking shoes, rainproof jackets, and cameras bags. We later found out that we could have avoided the lobby and stopped in the attached hotel store for a cream pie to go. Oh well.  

We dutifully checked out the Boston Massacre Site and the Old State House, but when we got to the markets across from Faneuil Hall, history was put aside. We strayed from our crimson path and found not only more Boston Cream Pie, but fudge, fish and chips, clam chowder, and other Boston fare. It should be noted that we did not eat ALL these things. Yet.    

After our market lunch we got back on track and headed to the North End. Any hope of following the trail was over at that point. The North End deserves to be wandered though. This Italian hub of Boston is way better than New York’s Little Italy. Every tiny street was packed with pizza-by-the-slice shops, bakeries selling over-sized cannolis, adorable restaurants with red checkered tablecloths, and dark inviting pubs. My friend and I started studying menus instead of historical information markers. We poked around wine shops instead of museums. We made dinner plans.

We ditched the Freedom Trail, headed back to our hotel to change, and returned for dinner the Florentine Cafe. We had some wine. I had the chicken-pork special. We had some more wine. Denise had pasta. And more wine. And more. Just as our waiter was hoping that we would pay him and leave, we decided to order bruschetta. And more wine.

“Seriously?” he’d asked, incredulous. Yeah buddy, we’re serious. Keep that food coming.

After our post-meal appetizer, we finally left the restaurant and realized that we hadn’t had dessert yet.

To Mike’s Pastry we headed.   The post-dinner crowd was loud and happy here, and we fit right in. I highly recommend the red velvet whoopie pie.

The next day we started at Bunker Hill, determined to finish the Freedom Trial. We made the 294 step climb up the Monument, thus working off 1/20th of our meals the day before.

We were about to head back to the North End and check out Paul Revere’s House and the Old North Church when my Dad called.

“Are you in Boston yet?” he demanded. He and my mother had been here a couple years ago (during baseball season, which made me jealous), and they talk constantly about how much they love the city.


“Isn’t it great?” he asked. “Have you gone to Warren Tavern yet? They have the best clam chowder…” Dad went on for awhile, about how it was a bar that George Washington frequented, how the fish and chips were great, and what beer had been on tap.

My Dad has had a lot of clam chowder in his day. And he usually doesn’t gush. If he says the chowder was good, it was probably REALLY good.

Plus, Warren Tavern is really close to the Bunker Hill Monument. So off the trail we strayed again. The chowder was so delicious, I ate it all before I could take a picture of it.

We did finish the Freedom Trail eventually. Good thing, because the Old North Church was my favorite stop on the tour. Well, my favorite non-culinary stop. A few days later I was digging through my purse and found a half eaten red velvet pie wrapped up in a Freedom Trail Map. Ahhh, good Boston memories.

Boston, Florentine Cafe, Mike's Pastry, The Freedom Trail, The North End, Warren Tavern

Jenna Vandenberg

Teacher, writer, runner, mom and wife.