This is pathetic.  I grew up in Massachusetts and went to college 20 minutes outside of Boston, yet as I’m about to leave for a trip back home I feel like I have no idea where to eat these days.  To be fair it’s been 10+ years since I’ve spent any real time in Boston, so I’m a bit rusty to say the least.  I don’t have much time in the city proper since the purpose of my trip is to go to Cape Cod for a week for a family reunion, but I do have almost 3 days.  Plenty of time to do some good foodie damage…and catch a Sox game of course!

I’ve done some research to supplement to my old favorites and what I’ve come up with is below. I’ve focused on things close to downtown where I’ll be staying and also made sure they were open either Friday, Sunday or Monday, the days I’ll be in town.  Since I don’t get back to Boston often I’m also keeping it a bit more traditional vs. exploring the fringe foodie trends that the city may be experiencing (next time!).  I want a reminder of the Boston that I know and love!

So take a look and let me know what I’m missing…especially you underground Boston foodies who really have your finger on the pulse!

I love me some brunch so even though I’m only in Boston for a few days I’ll want to try at least one brunch spot!

New England Clam Chowder:
Union Oyster House is a Boston landmark and to be honest I haven’t really seen many people talk about their chowder at all…but I always stop here for Oysters and to just hang out at the bar (I love this place!) and inevitably end up getting a bowl of chowder…as you can see in the first photo of this post!

I’ll likely go to Union Oyster House again this time and then compare it to a couple of the others (I know Legal’s is a chain, but honestly chowder is one of those foods that takes well to being made in massive batches and their’s is really good) listed below that people do claim have the best chowder in the city!  I’ll let you know my verdict…

There are so many good places to eat in Boston, but my heart belongs in the North End!  So that’s most likely where I end up.  Quite a few of the places listed under the Chowder and Cocktails sections of this post are also known for their great food and should be considered for good dinner choices as well.

  • Trattoria di Monica – I had my birthday dinner in the North End here about five years ago and absolutely loved it.  The exposed brick walls, the handmade pasta, the wine…it was all fantastic.  So I was happy to see that my favorite Boston-based food blogger (Tiny Urban Kitchen) had it on her site as one of her Boston recommendations.  It’s always nice when an old favorite is confirmed by others!

  • Prezza – this is the other restaurant in the North End that kept popping up in my search.  It’s a bit more expensive and popular so you likely need a reservation, but looks delicious.
  • Parker House  – this historical restaurant in the Omni Parker House hotel claims to be the birthplace of Boston scrod, Parker House Rolls and Boston Cream Pie.
  • Troquet – this French restaurant is on the pricier side, but if you’re out on Boylston street near the park it looks like a good choice.  It also sounds like they have great wine, so maybe even just stopping for a drink at the bar would be worthwhile.

If you’re eating in the North End try to use all of your restraint at the restaurant and save room for dessert at a local Italian bakery.  Mike’s pastry is my first and only choice, but there are a few other options for your sweet tooth (but please don’t leave town without a cannoli from Mike’s!)…

  • Mike’s Pastry  vs. Modern Pastry cannoli taste-off!  I am a die-hard Mike’s Pastry girl…no trip to Boston is complete without it. But this pesky Modern Pastry kept coming up while I was doing research as having the best cannoli in the city. Blasphemous!  So I’m going to have to go find out for myself.
  • Boston Cream Pie (at the Parker House listed above)
  • JP Licks or Emack & Bolios for Ice Cream

I’m a bit older now than when I used to party in Boston, so no more Purple Shamrock or Hong Kong for me.  These places looked a bit classier, like a good place to get a well-made cocktail and have some good conversation.

Rooftop Bars: 
Summer equals rooftop bars and drinking outside to me…but San Francisco isn’t the best spot for that this time of year so when I’m in warmer climates I’m on the prowl for good spots with sunshine (or a warm evening breeze) and a good view.

  • Legal Harborside – yes, it’s a chain restaurant, but they have some of the best chowder in the city and this particular location has a great open-air lounge with a nice view
  • Colonnade – this has a rooftop bar and a pool.  The price can be pretty steep for a full day of access, but after 3pm it drops to $25 to use the area and pool until close
  • The Landing – not a rooftop bar, but it is a fun outdoor patio right in the hub of it all – a bit touristy from what I remember though
  • A few others that look cool: Market  & Splash Ultra Lounge Ristorante Fiore

Live Music: 
I love live music, but I never seem to fit it into my normal life so whenever I’m on vacation I try to find ways to squeeze it in along with the drinks…

  • Howl at the Moon this is a chain dueling piano bar, which may seem cheesy but I’ve had more fun at these types of places than I can even explain!  For some reason I associate dueling piano bars with Boston, I’m not really sure why
  • Boston Harbor Hotel – The BHH is an iconic Boston building, so spending time here has a bit of a romantic and nostalgic feel to me.  Throughout the summer they have different outdoor live music and projected movie events almost every night.  Good summer-time fun!
  • Black Rose – it looks like they maybe have a house entertainer, Terry Brennan, who only performs on Monday nights, but this spot kept coming up near the top when searching for live music in Boston.
  • Avenue One (Hyatt) – this spot looks pretty laid back and cool with lots of options for music depending on the night and time of year. 
  • Lucky’s Lounge – they have a Sinatra night, which sounds kind of fun to me…

I love walking around markets and even grocery stores for that matter!  It really tells you something about the culture in my opinion…and they’re just fun to explore!

  • SOWA Open Market – This looks amazing to me…right up my alley so I will definitely try to hit it up on Sunday.  There’s  food trucks, a farmers market, artisan sellers and different events throughout the summer.
  • Faneuil Hall – of course!  Totally touristy, but there is some good food to be had in there.  And it’s just good old fashioned cheesy Boston fun.
  • Haymarket – Friday & Saturday dawn to dusk…but for those of us familiar with farmer’s markets this is more of a re-sellers market.  So good, cheap produce, but often bought from nearby stores right before it’s too ripe for them to sell.  This isn’t about supporting local farmers though, just to be clear.

So, what did I miss?  If you only had 3 days in Boston and were staying downtown what would be your top pics for good food and an authentic New England experience?  Spill!