I have spent a lot of time in Boston and love the city.  It is walkable, historic and has great nightlife and sports.  It also has a fantastic foodie scene and has many wicked good places to eat.

Boston is one of the oldest major cities in the United States and from its very inception it was declared by the people who lived there to be “one of the most important cities in the world”. At the time it didn’t mean much, but over time the city did in fact rise to prominence as the home of many of the country’s elite before the 20th century.

Boston was the catalyst for independence movements and several revolutionary battles were fought in and around the Boston areas and as these ideas of liberty grew, and the city emerged as a major hub of economic life, Boston also began to be a major city for people looking to make their living in the new world. 

Gradually the city’s working-class grew with populations from Germany, Italy, and especially Ireland, coming to the city to work. This led to the fabric of the city’s diversifying and immigrant enclaves each bringing in their culture and food and now in the 21st century, Boston stands as a cool historic, and food-friendly city. Check out some of the best places to eat in Boston.

Union Oyster House

Walking along the Freedom Trail is a quintessential Boston tourist activity and one of the stops on the trail is the iconic Faneuil Hall. Located practically next door, Union Oyster House is on the National Register of Historic Places and is the oldest continuously operated restaurant in the United States.

The building was established in 1742 and was mostly just a storefront and importer taking in goods coming to and leaving Europe. On the upper floors of the establishment, private discussions of revolution were starting to take place, and during the American Revolution, many of Boston’s women took to the building to sew and mend clothes.

By 1826 the building dropped its importer and cloth business and became an oyster bar. A semicircular bar was installed along with a kitchen and since then Union Oyster House was the destination for fresh New England seafood, even being a favorite spot of J.F.K who has a booth dedicated to him. While Union Oyster House serves a variety of seafood, the main draw is, of course, the oysters.

 The Paramount

Located on Beacon Hill, The Paramount is a throwback to the world of greasy spoon diners that seemed to be ubiquitous on every street corner before Starbucks and artisanal sushi joints took over.

The Paramount started its life in 1937 so the old school throwback vibes here are not only part of the charm but they are authentic as well. What makes this spot such an enduring icon is simplicity. Nothing is too fancy and basically, everything is cooked right there on the griddle. Start your day with an omelet or chocolate chip pancakes, and end it with a steak and potatoes. Or have breakfast for dinner or dinner for lunch or whatever other combination you can think of. 

Oleana

Small plates with big flavor is the name of the game at Oleana.

The fare here is Mediterranean influenced but it’s not your standard kebab and calamari.

The dishes are fragrant, filled with spices, but at the same very delicate. Ingredients are always fresh and locally sourced and even if you’re not in the mood for something heavy, simply snacking on the meat-free mezze plates will make a great (vegan-friendly) date idea. The wide selection of wines available will compliment every dish and for those that have a sweet tooth, their Baked Alaska is an intricate creation that might even rival some main dishes.

Grill 23

Despite Boston’s age, the city is a modern and cosmopolitan place.

Delicious vegetarian options and hipster cafes are not uncommon but when you’re looking to spend way too much money on huge pieces of meat, Grill 23 is there.

The restaurant was started by two brothers from Chicago who came to Boston looking for that quintessential steakhouse experience. Feeling like nothing like that existed at the time, they opened their own, and now for over 30 years Grill 23 is one of the best steakhouses in the city. Beef, seafood, and other ingredients are premium cuts and all-natural.

Cuts like 100-day-aged rib eye and Kobe cap steak fill the menu and if you’re looking to splurge even more the fresh 72$ dollar two-pound lobster makes a great add-on for some surf and turf. Finally, top off your meal with a tableside humidor presentation and enjoy a cigar from their finely curated selection.

Located along the Freedom Trail, check out the Union Oyster House, Boston’s oldest restaurant.

Giulia

Historically, Boston’s North End was the home of Little Italy, but in nearby Cambridge Giulia’s is making some headway in the world of Italian food in the city. Giulia serves some amazing elevated dishes that lean on classic Italian fares such as a thick and warming pappardelle served with slow-cooked boar or their selection of fresh fish with grilled vegetables. Finish it all off with a dessert like a caramel panna cotta with almonds, fresh figs, and currants.

Giulia’s is quickly becoming a hot spot so make sure to book a table in advance. 

The Daily Catch

New England and seafood are synonymous. Even as early as the 19th century, the city was enthralled with oysters, seafood, and whatever the fresh catch of the day is. Seafood is very much part of the fabric of the city but people’s tastes change over time, and what you’ll get at The Daily Catch is a touch of the old school with a bit of the new. 

Founder Paul Freddura was born and raised in Boston’s North End and learned how to cook and source seafood from the city’s old fishermen on the dock back in the 70s.

Fredduro opened his first place shortly after and while it was a small place it was good. Traveling up and down the east coast, Fredduro learned a thing or two more about the seafood game and retired, leaving his small restaurant to his sons. That small restaurant then grew to become The Daily Catch.

Traditions such as fresh seafood bought from the Boston Fish Pier is still a tradition that stands while flavors from the family’s Sicilian roots give the plates a touch of flair like lobster pasta, crisp calamari, and grilled seafood.

Tasting Counter

Tasting Counter is not just a place to get dinner, it is a show and an experience. If there’s one restaurant that lets you know that Boston is a modern cosmopolitan city, it is this one. Tasting Counter is pricey, so heading out here is a special occasion type of deal. Lunch comes in at around 100$ while dinner service comes in around 275$. Tickets are sold in advance and of course, once the meal is finished, you don’t have to worry about paying or tipping. 

So why is it an experience and why is it so expensive?

Tasting Counter breaks down the barrier between the kitchen and dining room.

The experience sits up to a small number of people at a time and offers a 9-course tasting menu taking place over two hours. The food and plates are cooked and prepared quite literally in front of you along with carefully selected drink pairings to go along with every dish. The U-shaped counter allows guests to watch while dishes are prepared, plated, and served taking guests along every step of the way. Guests are also encouraged to talk, ask questions, and sip a cocktail offering a level of interaction you won’t find anywhere else. 

Another great place to try is Brewers Fork.

Brewer’s Fork

Before Brewer’s Fork showed up this stretch of Charlestown was pretty quiet and devoid of restaurants, which made it before for a big and hip pizza joint to open up.

Now Brewer’s Fork has the hearts of Boston’s pizza lovers.

They opened up in early 2015 and even though it hasn’t been that long, Brewer’s Fork has quickly made a name for itself. Small plates, charcuterie, and yes, even oysters are available here but you’re really coming in here for the pizzas. Wood-burning ovens offer crisp crusts and delicious combinations such as the “killer b” served with genoa salami and hot local honey or the “bacon jammy” served with bacon jam, cherry tomatoes, and fresh basil. Brewer’s Fork has an outdoor patio dining and a long list of beer selections so book an outdoor table and pop on over with a few friends after work. 

Puritan & Company

Its name is an homage to the first people who founded New England but rest assured, Puritan & Company is anything but puritan. Located in Cambridge, the restaurant is casual and aims to take New England’s classic dining and dishes to a modern level. The menu changes pretty often depending on what is available but its influence on local fare means you can expect dishes like salt cod fritters, lobster stew, and scallops with wax beans.

But despite its Massachusetts-centric menu, guests can often find some other delicious standouts like a kimchi hot dog, wagyu beef carpaccio, and roasted duck breast.

Krasi

Located in Back Bay just off the iconic Boylston Street, Krasi is a Greek-themed restaurant that not only offers a little taste of the islands but their huge selection of Greek and international wines will make you feel like Dionysus.

The cool and modernly designed dining room makes hanging out with friends after workday a fun option while you indulge in some wine or check out their brunch menus with options such as a fried egg saganaki and pair it with a spiked coffee, mimosa, or ouzo-infused apricots. The staff here is equipped with a huge knowledge of the wines on offer so don’t be afraid to ask what dish will pair best with what wine. 

Tawakal Halal Cafe

After opening a pretty successful restaurant earlier in the decade, the owners had to close down shop in 2011. But they are back and better than ever offering some of the best Somali cuisine in Boston.

The ambiance here is casual and laid-back and for a pretty fair price, you’ll get a heaping plate of delicious food using flavors and dishes that not only highlight Somali fare but tastes from around North Africa and the Middle East as well. Homemade hot sauces, beef biryani, and beef tawakal tops most people’s favorites here.

Regina Pizzeria

A great pizza place has already been mentioned but you can never have too much pizza right? Regina Pizzeria has been operating since the late 1920s and there’s no sign of it even slowing down. Located in the North End, Regina Pizzeria has been so good for so long because of a couple of reasons.

For one, their oven has been their cooking surface since 1888. That’s right, the oven is older than the restaurant itself and it has never changed. Secondly, the folks at Regina Pizzeria let their dough proof for six days. This results in a crispier, chewier dough that’s still light and soft. There might be a lineup but if you get in, grab a spot by the bar, order by the slice and a cold beer, and enjoying one of the most authentic North End experiences you can get.

Our Final Word

Large walkable cities are becoming a thing of the past, but Boston remains so.  There is even a National Park where you walk to different buildings that were instrumental during the Revolutionary War.  There is so much to do in Boston, whether you go to a Red Sox game during the summer, whale watching off the coast or just explore, don’t forget to check out some fabulous eateries along the way.  What is your favorite place to eat at when in Boston?

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