Foodie Walking Tour of Boston Walking Tour

When you exit the T station, take Haymarket Square to the left to cross John F Fitzgerald Surface Rd and to walk through the green space. After you enter the green space take the path to the right, and your second possible left on the pathway. As we exit the green space, we will cross Cross Street to take Salem Street. This will lead you into the North End, where you’ll notice there is a plethora of restaurants to choose from, and they are all fantastic. Be sure to take in the environment of the red brick buildings and the narrow streets as you make your way to the first stop.

Continue on Salem Street until you can turn right on Prince Street. Walk past the Polcari Playground and Saint Leonard’s Church. Then, turn right on Hanover Street. Shortly after the turn you’ll be able to spot Mike’s Pastry on the right side of the street.

The large sign bearing the name of the pastry shop will obviously tell you that you’re in the right place, but the line out the door will be another clue. Mike’s Pastry is one of the most popular dessert spots in Boston. It’s not hard to figure out why; the traditional Italian pastries here are incredible. Make sure you check out all of the cannoli flavor options before grabbing one to snack on as you walk to the next stop.

Continue down Hanover Street from Mike’s Pastry and follow it through North End Park. Take a bit to relax in the park as you enjoy the pastries, then continue on Hanover Street until you can turn left on Union Street. This will take you straight to stop number two – Union Oyster House.

Try the oysters here, because seafood is a staple in Boston, but don’t get too caught up in the meal that you miss the history of this building. The restaurant is located in one of the oldest buildings in the city. Union Street was laid out in 1636 and it’s possible that this exact building has been standing more than 250 years. The gift shop celebrates this history and is worth a stop.

Continue on Union Street until you can follow the Freedom Trail, the red line on the ground, to cross North Street into Faneuil Hall Marketplace. Take the Freedom Trail past the Samuel Adams statue and up the right side of Faneuil Hall. Then follow S Market Street and take time to shop through the stores as this is one of the best areas for souvenir shopping. Once you’ve purchased everything you need, follow the path to the left until you reach the intersection of Commercial Street and State Street. The next stop will be on the corner on the right.

The Black Rose is a fun Irish pub with good ale and often has live music. At the least, stop in here for a beer and some entertainment. If you’re wanting a meal, obviously The Black Rose does Irish food excellently, but their Boston staples, the lobster roll for example, are tasty too. You really can’t go wrong with a place that lists “A Pint of Guinness” as an appetizer.

Turn right on State Street from The Black Rose and follow it until you can turn left on Congress Street. Congress Street will take you through the Financial District and past the Norman B. Leventhal Park. If you want a break from the concrete jungle, take some time strolling through the park or sit on a bench to relax for a bit. When you make your way to Purchase Street, take a right. Continue along Purchase Street through the Lincoln Street Green and the Chinatown Gate Park Plaza, then take a left on Beach Street, which will take you straight to the entrance of Hei La Moon.

Boston’s Chinatown district is saturated with incredible Chinese restaurants, so it’s a task to pick out which one is the best. Hei La Moon is definitely a standout, though, and incredible when it comes to dim sum. The lunch and dinner menus here are pretty standard and are definitely good, but the dim sum experience is way more fun, so we definitely recommend trying that.

From Hei La Moon, follow Beach Street until you can take a right on Lincoln Street, then take a right on Kneeland Street followed by a left on Harrison Avenue. Follow Harrison Avenue for a while and eventually it will lead you to stop five – Bar Mezzana.

Bar Mezzana serves some excellent Italian eats, for example, the crostini options are incredible. The real appeal of this place. though. is the cocktail list. Stop in for a refreshing drink, such as the Mezzana Spritz, which is made up of peach, campari, soda, and moscato d’asti. Maybe pair your cocktail with some gelato or a crostini, if you feel so inclined.

Continue down Harrison Avenue until you can take a right on E Berkley Street. Then take a left on Washington Street. Follow Washington Street past Peters Park and eventually it will take you straight to The Gallows.

The Gallows is a trendy gastropub that offers a really cool environment. Stop in here and take time to hang out and enjoy the gems on their menu. The Pork Belly Tacos and the Carbonara Mac are some of our personal favorites, but the real star of the menu at the Gallows is the Poutine. It’s listed under “shares” but no one will judge you if you want to keep it all for yourself. The cocktail menu is great here as well, so definitely check that out, and since it is a gastropub, the beer list is extensive.

Follow Washington Street past Franklin Square and Blackstone Square. As you walk along Washington Street, enjoy the tree lined streets, red brick buildings, and neighborhood feel of South End. This street will also take you past South End Burying Ground, which was opened in 1810 and was the site of criminal executions by means of the gallows in Boston. If you’re a history buff, explore the cemetery before returning to the walk.

Eventually, Washington Street will take you directly to Toro, which is on the left side of the street. For Barcelona-style tapas in a fun environment, Toro is one of the best options in Boston. The menu offers so much variety that you’re sure to find something to please everyone here. I personally would recommend the Mejillones or the Patatas Bravas.

Next up is the longest stretch of walking on the trip, giving you time to digest before the next stop. Continue on Washington Street until you can take a right on Mass Ave. Mass Ave will take you through Chester Park and into the Symphony area. Snap some pictures of historic Symphony Hall, which was built in 1900, then continue on Mass Ave. Follow the street as it curves around the Christian Science Plaza and when you reach Haviland Street, take a left. This street will lead you straight to Berklee College of Music and the Boston Conservatory, so this area is likely to be buzzing with students. When you reach Hemenway Street, take a right, then take another right onto Boylston Street to get to stop number 8 –Boston Burger Co.

Obviously, Boston Burger Co. claims a spot on this walk because of their exceptional burgers. The standouts on the menu are the Mac Attack and the Green Monstah, but the option to build your own allows for endless choices. However, if you’re not feeling a burger or don’t think you’re hungry enough for one, stop in here anyway because the milkshakes, or #freakfrappes, are amazing. The S’more Than You Can Handle is a life changing experience.

Continue on Boylston Street as it leads you past Hynes Convention Center and the Prudential Center. This area is full of great shopping, so keep your eyes peeled for stores that interest you as you walk. Take a left on Fairfield Street followed by a right on Newbury Street.

Shortly after you turn right is the entrance to Teuscher Chocolates. Be careful you don’t miss it, the entrance is down some stairs on the right side of Newbury Street. For some of the best Swiss chocolates in Boston, and an assortments of jams and pastries, Teuscher Chocolates is the place to go. Grab some sweets for yourself or souvenirs to gift to others.

Shop your way down picturesque Newbury Street for a couple of blocks, then turn right on Dartmouth Street. The entrance to the final stop, Lolita Cocina & Tequila Bar, is another one that’s kind of hidden, but be on the lookout for the black and red sign on the left side of the street. The entrance will be down the stairs.

What better way to finish a foodie walking tour than with a shot of tequila? Or at least some amazing quesadillas and maybe a pineapple margarita. Lolita offers a really cool vibe with some delicious food and an extensive drink menu. You really can’t go wrong with anything at this restaurant.

From Lolita, you can continue up Dartmouth Street into Copley Square. If you turn right on Boylston Street, you’ll be able to take the T from the Copley Station to anywhere else in the city. You could also easily grab a cab or walk down Boylston Street to the left to explore further into downtown.