Wicked Good Eats Boston's North End
Updated: Jul 21
Incredible food and drinks in Boston's North End
When I graduated from college, I stuffed three weeks worth of clothes into an overly large backpack, bought a Eurail Pass, and headed to Europe. I slept in hostels, pensiones, and train stations. I ate sausage and day-old bread on park benches. I saw another world as we backpacked across 7 countries.
The world I experienced was captivating, if for no other reason than it was old. The ancient world dripped from every well-preserved monument, church, and castle. And that sense of origin ran deep and dense through its people, cultures, and food.
Boston feels like that. It is rich with America's very complex history, and so much of who we are began there. Yet, it also possesses a character that it keeps uniquely its own. And that sense of self seeps into every cobblestone corner of the city.
There is so much in Boston that it's difficult for me to do justice to everything, but I'll highlight some of my favorites. Just know that Boston, like New York, is a great walking city, and you can see so much in one day on foot.
I recommend starting at The North End. Here, you'll find Italian restaurants, coffee shops, cannolis and the Freedom Trail, to name a few. Below are a few of the wicked good eats in Boston's North End.
This speak-easy themed gem has one of the best vibes in Boston.
One of our favorites, which came highly recommended by a Bostonian friend, is Parla. This speak-easy themed gem has one of the best vibes in Boston. Open-air in the spring and summer, Parla is a different take on the more traditional Italian eats you’ll find in The North End, but the real star here is the Dungeon Master.
That’s right, all you D&D fans, Parla is famous for their Dungeon Master cocktail game: you roll their 20-sided dice, and whatever it lands on is your cocktail. Don’t worry - they give you a “score card” to keep track of your progress through all 20. (So far, the Hotchata has been my favorite!) This isn’t for the faint of heart, so make sure you're an adventurous adult-beverage connoisseur before you give this a go.
Cannolis of all flavors, Boston Creme cake, macaroons, cookies…the list goes on and on.
And if you’re looking for an authentic cannoli, you’ve got a great option here: Bova's Bakery. Cannolis of all flavors, Boston Creme cake, macaroons, cookies…the list goes on and on. (You can also try out Mike’s, which has a location in The North End and Harvard Square. Both are delicious, but Bova is a bit less commercial and you won’t find the extremely long lines like Mike’s.)
When they say they’re famous for “outrageous, overstuffed sandwiches”, they aren’t kidding.
There are definite perks to have locals(ish) discover places for you. My son stumbled upon one such delicious find while exploring Boston his freshman year at college. Pauli’s (no “e”) is a hole-in-the-wall sandwich shop that has absolutely no frills. When they say they’re famous for “outrageous, overstuffed sandwiches”, they aren’t kidding. You can find a great lobster roll here, or you can order (as we did) one of their delicious sub sandwiches.
Pretty much everything except the kitchen sink goes on their sandwiches (so come hungry). Case in point: The Anthem (aka Mambo Italiano). Based on the name, I feel like you don’t need any description. And if you do, this sandwich is probably not for you. Suffice it say, there are a lot of chicken cutlets on Pauli’s offerings, so you should know going into it that it is not conducive to eating light.
The Thinking Cup
Honey Cinnamon Latte and a Cherry Ginger Scone...So, um, ok, listen - YUM.
One last highlight is The Thinking Cup coffee. I recently went to pack up my son from BU for the summer. While he slept in the day of our return flight, I got up to explore The North End’s coffee offerings. To my surprise, The Thinking Cup was right around the corner from our hotel.
So, um, ok, listen - YUM. It was spring, so that meant iced coffee season. I am a sucker for a latte, and the Honey Cinnamon Latte with oat milk was my choice here. The notes of honey came through in a delightful way that wasn't lost in the ice and cream. Of course, the best breakfast coffee pairing is a scone, and The Thinking Cup had me at Cherry Ginger Scone. I cannot adequately describe how that cherry and ginger combination beautifully danced across my taste buds. Wow. Just wow.
I also ordered a bagel with schmere for my son, and I was certain I misheard the guy who rang up my order. When he gave me my total, I told myself he must have said $30.50. After all, this is Boston. Nope - he said $13.50! I mean, y’all, you cannot beat these prices.
There is a LOT to see and do in Boston. My oldest son best described it this way: "It's not as noisy as New York and not as tall as Chicago."
My TOP Recommendations for the North End:
Walk The Freedom Trail - Because there is absolutely so much history to Boston, this excursion is a must. You can certainly pay a guide, but the National Park Service has an audio version you can get on your phone by downloading the NPS app for free. Bring headphones, unless you're going to share the audio version with family or friends. The best part is you can stop and start it at your own pace.
Eat a cannoli. Do it - even if you don't like cream. They are simply divine.
Go on a Ghosts & Gravestones ghost tour. This city is 400 years old, so there is a lot of murder and mayhem to tell. Touristy, yes, but the cast is incredibly entertaining and informative.
Catch a ferry to Salem. You do need to book this in advance, but the ferry ride alone is worth the money. About a 45-minute trip, the water is beautiful. Sure, Salem is also touristy in a witchy-kind-of-way, but it still delivers on history. I recommend reserving a private tour with one of the many guides available. You'll get a quick rundown of all the important sites and still have plenty of time to tool around town on your own.
Swing by Kane's Doughnuts for some truly interesting flavors. There are a couple of locations, not exactly in the North End, but they are worth a stop.
Just like San Francisco & New York, Boston has its own unique pockets of diverse cultures which played a significant role in its origin story. Here, the impact of Italian immigrants is still alive in the North End. And I would argue that all of these cultural areas have profoundly impacted our collective social consciousness through their unique food contributions . That’s why we seek them out when we travel.
And for all the noise lately, this is what makes us who we are: diverse people enjoying all the meals we bring to the proverbial table.