How to Spend St.Paddy’s Day Weekend in Boston, Massachusetts

Let’s be honest, if there is any place I’d most want to spend St. Patrick’s Day, it would be in Boston.

Okay, maybe Ireland would be my first choice, but Boston is definitely a close second despite my aversion to overpacked bars and unnecessary chaos. In fact, compared to some of the St. Paddy’s day celebrations I have witnessed in my own state, the one’s in Boston are relatively calm. Boston is a fun weekend getaway for those in the Northeast in general, but come St. Patrick’s Day weekend, there are even more experiences to be hard.

  1. See the Dropkick Murphy’s live from Boston’s House of Blues.

Attending a Dropkick Murphy’s concert during St. Patrick’s Day weekend has become a staple event when visiting Boston for the holiday. The Dropkick Murphy’s are one of those bands that are absolutely fantastic live regardless of where and when you see them; but even the upper-mezzanine seats at Boston’s House of Blues give you access to a great view and two bars with drink prices that won’t break the bank. The band even brings out a bagpipe player for tracks like “The Spicy McHaggis Jig” and Irish step dancers for their most popular song, “Shipping Off to Boston”, making this a pinnacle of Irish festivities in Boston.

How to Spend St.Paddy's Day Weekend in Boston, MA | Northeast, United States Travel | St. Patrick's Day | AGBHOW |

2. Grab a post-concert sweet Italian sausage outside of the House of Blues.

If you’re like me, you’ll probably end up grabbing a pre-concert sausage to inhale while waiting on line to enter the venue as well. During concerts and ballgames at Fenway park, you’ll find these sausage stands up, running, and waiting to serve street delicacies like hot dogs, sausages, and beef tips.

In more recent years, some street vendors have noted a slight decrease in visitors as many choose to stop by chain restaurants like Wahlburgers before local events. PSA: If you have yet to ever try Wahlburgers, do not spend your money at Wahlburgers. But if you have the opportunity to grab a $9, almost footlong loaded Italian sausage, spend your money.

How to Spend St.Paddy's Day Weekend in Boston, MA | Northeast, United States Travel | St. Patrick's Day | AGBHOW |

3. Skip the hotspots when bar hopping. 

If waits in potentially freezing weather, cover charges, and standing chest-to-chest with sweaty strangers who pre-gamed way too hard seems like your cup of tea Guinness, then by all means head on over to the West End. But if you prefer a good-sized crowd that still allows room to breathe, good energy, a shot at grabbing a table, and four dollar beers, then the Fenway area might be for you. While these areas aren’t necessarily known for their strips of bars, you’ll a handful that’ll offer you a great time. And isn’t quality over quantity better anyway? We could’ve spent hours at spots like Puddingstone Tavern where the drinks are cheap, the crowd is chill, and you’ll find every board game to drunkingly challenge your friends to.

We too are guilty of wanting to follow the crowd, however. After a couple of hours of playing Phase 10, we actually headed over to the West End. I can say with no exaggeration, that we lasted approximately a half hour before heading back to our new favorite bar. Up the block from Puddingstone, you’ll find Flann O’Brien’s, which on St. Paddy’s day even hosts a $15, all-you-can eat corned beef and cabbage buffet.

How to Spend St.Paddy's Day Weekend in Boston, MA | Northeast, United States Travel | St. Patrick's Day | AGBHOW |

4. Have a bite at America’s oldest restaurant.

During your St. Paddy’s day weekend getaway, there are really only two reasons to visit the West End – the Freedom Trail and Union Oyster House, which is apparently American’s oldest restaurant. The building itself dates back to the post-revolutionary war era and is an official historic landmark, thus the building and booths themselves are quite snug. As a restaurant, this spot has been serving food since 1826 and is most known for their oysters, if that wasn’t obvious. While I wouldn’t say this place offered the best food I’ve ever had, my opinion may be a bit skewed since I’m highly allergic to oysters and therefore had to pass on what was apparently some amazing clam chowder. But the atmosphere of dining in a place of history is worth a visit. Plus, the complimentary cornbread is probably some of the best I’ve ever tasted. And if you have some time post-meal and are interested in some Boston sightseeing, this restaurant sits right in the center of the Boston Freedom Trail.

How to Spend St.Paddy's Day Weekend in Boston, MA | Northeast, United States Travel | St. Patrick's Day | AGBHOW |

5. Make sure you have a breakfast spot picked out to ease your St.Paddy’s Day hangover.

Nothing cures a hangover better than a good breakfast platter, which is why many breakfast spots will be packed out. Luckily, we stumbled upon Milkweed pretty early and were only given a 30 minute wait, which not only allowed us time to grab a quick drink at the bar across the street, but also proved to be more than worth the time.

The platter below included eggs, bacon, sausage, ham, home fries, and the most amazing french toast! PSA: For an extra $2, you can trade in your simple-yet-delicious french toast for one of Milkweed’s signature options, such as Nutella french toast or Lucky Charms french toast. With a coffee, I think I paid roughly $12, making this a bargain and a win in my book.

How to Spend St.Paddy's Day Weekend in Boston, MA | Northeast, United States Travel | St. Patrick's Day | AGBHOW |

Whether you come to celebrate St. Patrick, to cheer on the Celtics, or for absolutely no specific reason at all there are so many things to do in Boston.

Already planning your next St. Paddy’s Day getaway? Pin this for later!

How to Spend St.Paddy's Day Weekend in Boston, MA | Northeast, United States Travel | St. Patrick's Day | AGBHOW |


13 thoughts on “How to Spend St.Paddy’s Day Weekend in Boston, Massachusetts

  1. This is great! Love the breakfast hangover haha. Ever since I heard they turn the river green I’ve wanted to spend a Pat’s day there!


  2. I didn’t know that the Dropkick Murphy’s played a St Paddy’s Day show in Boston! That seems like critical information that my Boston-raised coworker should probably have shared with me. Planning a trip over for this next year now!

    Liked by 1 person

  3. I’m not much of a drinker but I’d love to experience the atmosphere in Boston during the St Paddy’s day. I think I’d focus more on the food.


  4. Pingback: My Year in Review: The Outcome of my 2018 New Year Resolution | A GREAT BIG HUNK OF WORLD

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