48 hours in new england


my lady and i took a trip to new england last september.  it was epic and really the beginning of this whole 48 hours concept.  how did we do it you ask?  well, i’ll tell you.

we landed in boston around 5:30 friday afternoon and rushed our asses to the rental car terminal.

travel tip #1: it was a good 20-30 minute ride on the airport bus to get there and then another 25 minutes to get the car because really old people love that part of the country and they ask a lot of questions at the rental car kiosks.

the reason the time was important was because we had red sox tickets for the 7:05 game.

travel tip #2: if the rental car company offers you the auto-pay toll doohickey, take it.  there are 1 billion toll roads in new england.  one billion!

the good news was that our hotel was a short 15-20 minute car ride from the airport.  the bad news was that i used hotwire and they gave us the westin copley place hotel.  i do not recommend this hotel if you are under 50 years of age.  they gave us the “hotwire” room which was akin to a broom closet i.e. we were next to the actual broom closet on the corner  of the floor with a view of what might as well have been the trash dump.  i hate hotwire.  never using it again.

we picked back bay (where our hotel was) because it’s close to fenway park.  we didn’t end up getting to the game until the 4th inning, but that’s ok because we made it just in time for a home run, a hot dog, and a cold beer.  fenway is amazing btw.  do not miss an opportunity to catch a sox game if you’re up there during baseball season.


travel tip #3: wait as long as you can on stubhub to get tickets to the red sox game.  i got ours at 5:30 and paid $30 a ticket.

the next morning, we woke up super early and did what any good new englander would do: we went to dunkin donuts.  do not worry if you miss a dunkin donuts because there will be another one 50 feet from the one you just passed.  they are fahkin everywhere.


our next stop was kennebunkport.  that drive is about 1.5 hours from boston and super easy.  we were there by 10 o’clock with a drink in our hand at the floating boat restaurant better known as the spirit of massachusetts.  we skipped the food there and walked around kennebunkport for a minute.  i wanted to hit the clam shack (above) for a lobster roll, but my traveling companion wasn’t hungry, so she made me wait.  their lobster rolls looked amazing but they were over $20.  wtf clam shack.

the very knowledgeable bartender at spirit recommended we walk to the bush’s summer home (walker’s point), because a) it was a pretty day and b) the walk was legit.  she wasn’t kidding.  there were some of the prettiest homes i’ve ever seen on that walk.  you can’t get super close to the bush’s compound (for obvious reasons), but here’s a shitty pic i took of it:


after saying goodbye to the bushes, we set out for lunch at one of their favorite spots on the walk back: mabel’s lobster claw.  i went with the lobster roll and fries (below) and alex got the lobster meat salad.  both were excellent choices.  we finished with the blueberry pie (also below).  holy shit.  go to mabel’s and get everything.



kennebunkport is a quick 35-40 minutes from portland.  we rolled into the city around 5pm and checked into the press hotel.  the press is my kind of hotel.  it used to be home to the portland press herald newspaper hence the display of typewriters you see in the photo below.  the rooms each have a writing theme and you can type a note to someone on the typewriter in the lobby.  it reminded me a lot of an ace hotel with a less hipster vibe.

travel tip #4: always ask the hotel about room upgrades.  we were bumped up to a suite on our second night simply by asking if any were available.  score. 


portland is no stranger to good restaurants.  there are a ton of killer spots in the tiny city.  the first one we went to was a place called duckfat.  they are known for their fries which are cooked in…can you guess…do you know what it might be?  yes, duck fat!  they’re amazing.  they might be the best fries i’ve ever eaten.  they serve paninis too which both of us didn’t love.  go for the fries and beer.  we actually went back the next afternoon for a fries appetizer.


the next day we decided we would make the 20 minute pilgrimage to freeport, maine to check out the birthplace of l.l. bean.  before we left we grabbed some donuts from the holy donut.  i got a maple bacon number that was pretty damn good and i can’t remember what alex got (most likely donut holes and a chocolate).  their donuts are made from potatoes which sounds really strange, but you wouldn’t be able to tell because they still taste like donuts.


l.l. bean is interesting i.e. it has to be the birthplace of dad jeans (if you catch my drift).  remember when they did the signature collection a few years ago and we all went nuts over blue bean boots?  that now feels like a distant memory.  look, i’m not hating on l.l. bean by any means.  it’s iconic and definitely worth the trip from portland, but there’s not a lot in there for us younger folks unless you brave the new england winters or need to buy christmas gifts for your grandparents.  we did get our picture taken in front of the giant boot which is a must if you’re a first timer.


on the way back from l.l. bean, alex wanted to check out the cape elizabeth lighthouse which is coincidentally next to the lobster shack.  i read about this place online after googling best lobster rolls in new england.  i wish i had a picture to share that was of the food rather than these trash cans and rundown shack, but i wasn’t really into taking pictures of food at this time period in my life.  their lobster roll secret is a nice size dollop of mayo and paprika on top of the lobster rather than in the lobster.  i still wish i had a picture of that lobster roll.  you can find one if you google it.  i just didn’t want to steal anyone else’s art.  😉


sunday afternoon we went to the allagash brewery.  it was a 20 minute uber drive from our hotel.  our uber driver was a bit sketchy and almost ran over two separate groups of people while yelling a made-up language out the window, but you probably didn’t need all that info.  what you do need to know is that allagash white is the jam and definitely a beer you should try should you get the chance.  the brewery gives free tours and free flights to those that stop by.  after we finished there, we went to the lesser known austin street brewery which is across the street.  i didn’t love their beer as much as the allagash, but the weather was nice and we were able to sit outside.

upon our return to the portland city limits, we were still thirsty for more libations, so we googled cool bars in portland and found a speakeasy down the street called the bearded lady’s jewel box.  it’s truly a speakeasy in the sense that we walked by it twice before figuring out it was behind a curtain with no signage (duh).  i wish i had a picture of this place, because it was impressive.  the cocktails were amazing and the owner / bartender was very welcoming.  it’s everything you would want in a speakeasy.


since portland is loaded with good food options, their restaurants fill up fast.  if you want to hit one of the better restaurants in town you need to try to make reservations or show up early enough to get a table.  we didn’t do either so we waited and waited to eat dinner on sunday night.  and i’m glad we did.  we went to a place called eventide oyster co. that was rumored to have the best lobster roll in town.  it did.  it doesn’t look appetizing from the picture above, but it’s one of the best things i’ve ever put in my mouth.  we also had the chicken bun which was also good.  for dessert, we split a homemade ice cream sandwich.  if you go to portland, do not miss eventide and do not fear the wait.

travel tip #5: they sit the bars at these restaurant, so don’t go in thinking you can just grab a seat at the bar.  that kills me.  bars should be first come first serve always.  

while waiting for our table at eventide, we grabbed a drink at their sister restaurant the honey paw.  this is another spot you should check out if you have time.  we tried the wontons and had a couple of drinks.  they were also playing records on a turntable.  that’s one way to win me over.


on our last day, we took a walk around portland and headed back to boston with a stop at petey’s summertime seafood in rye, new hampshire.  this was another google find and another lobster roll.  if you’re keeping track, that’s 4 on the weekend.  if alex wouldn’t have been with me, i might have eaten 10.


we got to boston early and to kill time i made alex go to ball and buck with me.  i’ve been upset with that place ever since i missed out on their first round of new balance x ball & buck a couple of christmases ago.  i got over it quickly after finally seeing their store in person.  great store.  the dudes working there were super nice too.

if you thought this was the end of our journey, think again.  we made one more stop before going to the airport.  alex wanted a cannoli from the famous mike’s pastry in little italy.  i’ll be honest, they weren’t as good as she made them out to be, but i did enjoy seeing that part of town.

that’s it.  that was our trip to new england.  you can do the whole thing in 48 hours for sure.  and to be honest, you probably only need one night in portland.  hotels aren’t cheap these days.  did i just say that?  maybe i should be shopping at l.l. bean after all.

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