Field Trip: Eating My Way Around Boston

What if you had a day — just 24 hours — to experience Boston? Where would you go? What would you see? And more importantly, what would you eat? Tough questions, right?! With so much history, interesting architecture, and mouth-watering food, the list of options might be overwhelming. Would you follow the Freedom Trail, exploring the city’s oldest neighborhoods and historical sites? Or would you take a cultural tour, visiting museums, Harvard Square, or maybe even Fenway Park? And the food — where to start?! From the classic — lobster rolls and cannoli — in the North End to the fine-dining restaurants in Beacon Hill, you could spend weeks doing nothing but eating your way through the city. (Yes, please!)

So with this dilemma at hand a few weeks ago, I went into full-on planning mode for a day of indulgence in Boston. Adding to the excitement was the fact that this would be my first trip to Boston since a family vacation many, many years ago that involved seeing much of the Northeastern US over the course of 10 loooong days while squeezed into the back seat of a VW Squareback with my siblings. The highlights of that trip included plenty of boredom, bickering, and parental threats of “One more time, and I’m turning this car around!” A long time coming, but I was getting my very own Boston do-over.

Given the limited time and transportation options (I was going sans rental car), I knew I had to have a tight game plan if I was going to make the most of my free day in Boston. My home base was the Hyatt Boston Harbor, a 10-minute shuttle ride from Logan Airport. The hotel sits right on the inner harbor, and on a clear day you have a gorgeous panoramic view of the city skyline. Being right on the harbor also means easy access to water taxis, a fun (if slightly damp) way to get into the heart of downtown in just about 10 minutes. Less time in transit and more time for fun and food!

With transportation at my doorstep and a keen interest to mix historical touring with some of Boston’s best food, I had my plan: I’d take a water taxi across the harbor to the Boston Aquarium drop-off point, walk up and over a couple of blocks to Faneuil Hall to pick up the Freedom Trail and start my self-guided tour. Using the Freedom Trail phone app, I’d be able to not only get the deets of each historic location, but I could use the map to pinpoint food shops and restaurants along the way so that I could jump off the trail and indulge in some of Boston’s tastiest food as the mood struck.

I wish I could say that my day of touring was one of those calendar-worthy East Coast fall days: sunny, crisp, and accented with a backdrop of richly hued fall color, but unfortunately, no. A big storm had blown through Boston the night before my planned day of fun, leaving behind grey skies and slick, wet streets pasted with those colorful fall leaves. The fall color I was hoping to see was everywhere I looked — as long as I was looking down. No matter, there were other sights to see and a lobster roll to be had.

Gettin’ My Seafood On
After checking out Faneuil Hall Marketplace — a collection of food stalls that cover just about every cuisine you could imagine — and touring Faneuil Hall itself, I picked up the Freedom Trail and headed over to the North End. Eventually I’d get to the Paul Revere’s statue, the North Church, and Copps Hill Burial Ground, but first up: Neptune Oyster, one of Boston Magazine’s winners for Best Lobster Roll

Sampling East Coast seafood was the priority of the day, and I was looking forward to my first actually-made-in-New England lobster roll. (Side note? My first lobster roll experience happened right here in the 650 at Burlingame’s New England Lobster. I wanted to see how the West Coast version compared to the original.) Not just about lobster rolls and oysters, Neptune Oyster serves a variety of seafood options, including a full raw bar, clam chowder made to order, contemporary crudos, and seafood salads. Anticipating an early lunch and wanting to sample as much of the menu as I could, I’d skimped on breakfast.

Neptune Oyster in Boston's North End
Neptune Oyster in Boston’s North End

Neptune Oyster is an intimate spot just a couple of blocks off busy Cross Street. In fact, the restaurant reminds me a lot of Swan Oyster Depot in San Francisco, but without the long line outside. Both places are small, with limited seating and a long, no-reservations waiting list. At Neptune Oyster you roll up, give your name and phone number to the nice man at the door, and then find something else to do for an hour or so until your spot is ready… unless you luck out for a seat at the bar (which I did!).

The restaurant’s interior is classic early 20th-century styling with subway tile on the walls, old globe lights hanging from the painted tin ceiling, and a marble-countertop bar. Servers are friendly, chatty, and ready to answer questions about the menu or offer wine-pairing suggestions. Want to start with something from the Raw Bar — oysters, clams, or a seafood cocktail? Of course you do! Just fill out the tally sheet provided with your menu.

Tally sheet for fresh oysters, clams, and seafood cocktails
Tally sheet for fresh oysters, clams, and seafood cocktails

I was jazzed to see some of my favorite West Coast oysters on the menu, but hey, I was going East Coast all the way: Wellfleet and Thatch Island oysters with a server-recommended rosé to start.

Oysters to start with a glass of crisp, yet fruity rose
Oysters to start with a glass of crisp, fruity rosé

I loved that the tally sheet included short flavor profiles to help me decide which oysters to try. The Wellfleets were smaller than the Thatch Islands, less plump, and really salty, whereas the Thatch Islands were plump and flavorful with a rich finish (my favorite of the two).

The main attraction for me, however, was the Maine Lobster Roll, served either cold with mayo or hot with butter. I opted for the cold version with just a touch of mayo. The sandwich comes with a mound of french fries that have just the right mix of salt, softness, and crispness — soooo good that you don’t want to stop eating them, (but I did, because, well, lobster). And the lobster roll itself? Simple perfection! Super-fresh lobster meat, and lots of it — twice what Burlingame’s NEL serves on their sandwiches — with just a touch of mayo and salt and pepper. (By comparison, Neptune Oyster’s sandwich is bigger than New England Lobster’s, but pricier, too. I was happy to see that our 650 version stands up to the East Coast original.)

A mound of fries, a mound of lobster meat, a freshly grilled roll... what else do you need?!
A mound of fries, a mound of lobster meat, a freshly grilled roll… what else do you need?!

After a thoroughly enjoyable lunch, including some entertaining counter-mates, it was time to waddle out of Neptune Oyster and get back on the Freedom Trail. After checking out Paul Revere’s statue and the Old North Church, I had one more food stop in the North End before heading over to Boston Common and Beacon Hill.

Statue of Paul Revere near The Old North Church
Statue of Paul Revere near The Old North Church

Holy Cannoli, Batman
You need to know that there was no way I leaving the North End without indulging in a classic cannoli! (Good thing I took a little time to walk off some of that lobster roll.) While anyone who knows cannoli in Boston will likely tell you that the two best-known bakeries for this crispy/creamy treat are Mike’s Pastry and Modern Pastry, I opted for winner of Boston Magazine’s Best Cannoli for 2012 and 2013, Maria’s Pastry.

Maria's Pastry cannoli filled to order: classic ricotta filling with chocolate chips and fruit
Maria’s Pastry cannoli filled to order: classic ricotta filling with chocolate chips and candied fruit

The crispy, deep-fried shells are filled to order with your choice of traditional sweetened ricotta, vanilla cream, or chocolate cream. Want to dress up your cannoli? Order extras like a chocolate-dipped shell, chocolate chips, or candied fruit. (Uh, apparently most people only go for one “extra” because ordering both chocolate chips and fruit got a disapproving look from the lady behind the counter. Whatev…)

Maria’s sells other traditional Italian pastries as well, such as sfogliatelle, torrone, and biscotti. Take your treats to go, or enjoy them at one of the shop’s small tables. (Note to self: don’t eat cannoli outside on a windy day, unless you want to spend the rest of the afternoon dusting powered sugar off your coat, your boots, your hair…)

With my cannoli needs satisfied, I dusted myself off and got back on the trail. I had an afternoon of sightseeing ahead of me.

There’s more touring and more food to come! Grab a snack and stay tuned for Eating My Way Around Boston (Part Deux).

6 thoughts on “Field Trip: Eating My Way Around Boston

  1. Hi, Annie – sounds like a great trip – but I always stop in at Legal Seafood for oysters and something from the grill. They are great and reliable.

    1. Hi Kurt! It was a great trip, and Legal was my planned dinner spot. Didn’t make it this time, but will definitely put it at the top of the list for next time!

  2. I am jaded about lobbie rolls. They are certainly great in Boston. We have a food truck, yes a food truck, serving lobster rolls once a week in my metro DC burb. We have a couple of Maine lobster companies with daily fresh lobster meat. My wife is from north central Mass and we have some off the beaten path spots for huge and fresh lobbie meat. Now if we are talking Maine …

    Anyway, if I had 24 hours in Boston, I would probably hit Santarpios, to confirm it is still one of the 2 or 3 best pizzas I have had. Some people have told me I simply must try Regina’s pizza. OK, I will!

    Like you, I would likely skip breakfast. In fact, I would probably hit one of those cannoli shops mid morning and another mid afternoon.

    For my other meal, I am thinking North End Italian, Irish pub, or BBQ. Boston does BBQ well. Red Bones is one place I went many years ago and I am willing to try a different place next visit.

    1. Love your food tour ideas, Charles! I think I’ll have to steal a couple of those for my next visit to Boston. (Oh, and Maine… I dream of a week in Maine during which I would eat my weight in seafood. :-))

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