Where to Eat and Drink in Boston

Last updated on December 31, 2019.

Hopefully you read my last post all about finding budget-friendly things to do around Boston. Well, now it’s time to eat! Some of the places mentioned before include restaurants, but those known more for their locations than their food – Top of the Hub and Cheers. Here I’m going to focus more on where to eat and drink in Boston.

Faneuil Hall & Quincy Market

Quincy Market is jam-packed with restaurants, so go and have a field day! You have so many options, it will be hard to choose just one. You might need to make a few trips there.

Union Oyster House

No trip to Boston is complete without a stop at Union Oyster House! As the oldest restaurant in the United States, it is a National Historic Landmark and an obvious place to visit. But, also obviously crowded! I found that the best time to visit is later in the evening, after the dinner rush. At that time, the crowds are gone and the kitchen is almost closed. But, seat yourself in the Freedom Trail room, order a bowl of clam chowder, and enjoy all of the artwork around you! The history of Boston is documented on the walls in these beautiful three-dimensional pieces of art. Beautiful!

Cannolis & More

One of the things that Boston is known for is its Italian area – “Little Italy” – except theirs is better than most! I know, I know, Boston is the Irish city, but darn, they know how to do Italian too! One of the best meals I’ve ever had was at Bella Vista on Hanover Street. Super friendly and accommodating staff (even when we didn’t have a reservation!) and downright delicious dinner.

But the most famous food of Little Italy? Cannolis! And just like Philadelphia has its rivalry for the best steak sandwich, Boston has its cannoli rivalry (check out this article on Thrillist). Mike’s Pastry is my go-to, just because sooo many of my friends have recommended it. Yes, I have friends that drive from Syracuse to get their cannolis to bring home for friends! Mike’s has a mixture of traditional and creative flavors. Don’t be surprised if you get overwhelmed! The lines are long and the menu is longer. Order anything. You won’t be disappointed.

If you’ve got a sweet tooth and you’re along the Freedom Trail, check out Sweet Bakery Boston. They have an endless menu of creative cupcake flavors – including some for your dog! The shop is adorable and definitely worth a quick stop.

Sam Adams Brewery Tour

In my previous post I talked about the free tours available at Sam Adams. But because we always look for the most unique experience, we actually did the “morning mash-in” tour. This tour does accept reservations, but also requires tickets for $10 each. The perk? You get access to the first tour of the day including the tasting room before anyone else, an extra sample of a new, sometimes experimental, beer, and a 5 oz. souvenir goblet. Worth it! Our tour guide was fantastic and the tour was one of the best I’ve been on. And don’t forget about going to Doyle’s Cafe after for your free pint glass!

Other Boston Breweries

Of course Sam Adams wasn’t the only one we visited! Check out these other ones and why I liked them:

Lamplighter Brewing Co.

Lamplighter shares its venue with a local café, has an awesome vibe (and style that I LOVE!), and hosts trivia. My favorite beer? Group Theory! It’s a wheat beer with chamomile and honey (it has my name written alllll over it!). I also loved their coffee beers: After Midnight (a stout) and Cuppa (a pale ale). Check them out!

Night Shift Brewing

I love Night Shift! Besides the adorable owl logo, they have a nice selection of great beers and I love the names (like Orville Schwarzenbacher, a roasted corn beer). My favorite, unsurprisingly, is Awake, a chocolate coffee porter. There are several beers on tap as well as nitro coffee, maple water, and seltzers. Something for every taste!

Bone Up Brewing Company

Bone Up is located right across the street from Night Shift. The venue is small, but cozy. There are a few games to play, snacks for sale, and the flights are served in muffin tins. How cute!

McGreevy’s

During my last visit to Boston, my sister-in-law came with us and her one “bucket list” item was to visit ‘the bar that Dropkick Murphys owns’. Well, knowing me, I will help anyone check off those bucket list items! After just a little research, my husband and I found McGreevy’s! Priding itself as “America’s First Sports Bar”, McGreevy’s has a long and interesting history. The celtic rock band bought and reopened the pub in 2008 and plays homage to that history on its walls. For any sports (or Dropkick Murphys fan – I happen to be both!), McGreevy’s is a must-visit in Boston. And if you’re lucky enough to visit when the Patriots are playing, you’ll find a cup of red, white, and blue confetti on your table to toss when they score a touchdown. (As a Miami Dolphins fan, this part was a little hard to swallow, but my Boston friends loved it!)

As far as food goes, it’s so much better than your average bar food. We were there for Sunday brunch, so we all got a variety of dishes, ranging from French toast sticks (omg they were amazing!) to fresh oysters (for only $1 each!). Everything was great and I can’t wait to head back again!

Looking for a way to save money on activities in Boston? Check out CityPASS (I get a teeny tiny commission to help maintain my website if you do!)

A4cade – Bar and Arcade in 1!

So after we had a huge meal at McGreevy’s, my friends led me to Roxy’s Grilled Cheese. Right away I had two thoughts. First, “There’s a grilled cheese restaurant featuring all kinds of grilled cheese?! Yes please!” But secondly, “How the heck do they think we are going to eat again? We just ate!” Fortunately (or not?) we weren’t there to eat. If you walk into Roxy’s, you’ll notice a big commercial refrigerator door that seems a bit out-of-place. But that door has a bouncer sitting in front. Why? Because it’s the ‘secret’ entrance to A4cade, a bar arcade! What?!?

Inside A4cade, you’ll walk into a room full enough arcade machines – both classic and modern. In the back there are basketball and skeeball games too. There are two bars – on in the front left and a larger one in the back. I loved the creativity of the shelves and wall murals – they made it look like a screenshot of classic Mario! The drink menu is all inspired by various games and ‘nerdy things’ – awesome! Definitely a unique place to check out, so get yourself over there to play some games and sip some cocktails.