Weekend Trip to Portland, ME: Lobsters, Donuts, and Lighthouses


Edit: My favorite Modcloth “Stripe It Lucky Skirt” in black and white that I wore in this excursion is now on sale for 25% off! Link here.

As you all know, I’m very new to life on the East Coast and I’m so excited to explore nearby cities during these *gasp* FREE weekends (Yes, still reeling at the thought of having 2 whole days off per week after a year of not having them!). After seeing some of my friend Ashley’s amazing food pics from Portland Maine, I knew I had to take a trip there!

Just to warn you, this is going to be heavy on food reviews!

How to get there:

M and I made it a three day weekend kind of trip, renting a car and driving from NYC to Portland Maine in about 6 hours. This was a sad and more tiring alternative to flying, but flights were about $450 round trip per ticket for this particular weekend. I would definitely advise flying, which is a short hour and a half trip between NYC airports and Portland, ME. Once you’re there, you can get around most places without a car, unless you want to visit the breweries or Fort Williams, which you can easily use Uber or taxi to get to.

Where to eat:

Where not to eat is the better question. I had no idea Portland has such a huge foodie scene! We got so many great recommendations from friends but sadly our stomachs could only take in so much food. Some places you have to try are:

  • Street & Co: An adorable place on a cobblestoned line alley with a huge open kitchen that reminds me of Casanova back in Carmel where I had my engagement dinner. The famous dish here is the Lobster Diavalo which consists of an entire lobster split down the middle tossed with mussels, clams, calamari on top of a huge bed of linguini in spicy tomato sauce. This was our first meal and it was one of the best meals of the weekend. Easily fills 2-3 people depending on how hungry you are. Also a fantastic deal, costing < $60 for a truly hearty and delicious seafood meal. We also got a delicious bottle of Gewurztraminer wine for only $39.
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Getting ready for dinner after a long day of driving! Please excuse my wrinkly shirtdress :P

Lobster Diavallo

Lobster Diavallo

  • Bite into Maine: Best lobster roll I ever had in my entire life. This is a simple food truck at Fort Williams Park with the freshest lobster, the most flavorful buttery roll, and the best views to feast your eyes on while you feast on your lobster roll. The rolls cost ~$16 apiece and they have different flavors like picnic (comes with coleslaw and celery salt), curry, Maine style (plain), and wasabi. Grab a blueberry soda and a bag of Cape Cod chips and enjoy your meal at one of the many picnic benches in the beautiful park.
Lobster roll with a view!

Lobster roll with a view!

  • Five fifty-five: This restaurant was just a block away from the Westin and had more space for walk-in’s. The interior is so cozy and looks like a home and the service is super friendly. We shared the mussels to start, the lobster truffle mac n cheese, and the seared scallops, finishing with the peach crisp and sour cream panna cotta. The food here is very RICH and filling. Sadly we couldn’t even finish the mac n cheese because aside from 2 pieces of poached lobster and lots of truffle, the rest were noodles in a very thick and creamy cheesy sauce. The mussels and scallops were excellent, as was the dessert. With all the other great dining options in Portland, I’d suggest coming here only if you can’t get a res at the others.
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Lobster truffle mac & cheese

  • Bard coffee: Cute shop with nitrogen coffee chilled with liquid nitrogen for a smoother pour as well as a mean Vietnamese coffee. Just up the street from Holy Donut so grab a coffee to go here!
  • Holy Donut: HOLY moly these donuts are GOOD. Rated one of the top 10 donut shops in the US, all the donuts here are made with the secret ingredient: potato. We tried the dark chocolate sea salt, fresh lemon, ginger and sweet potato glaze, and the brandy coffee glazed donuts. My personal favorite was the ginger and sweet potato; we even went back for seconds on this one. The donuts are very thick and taste more like cake than donuts. They’re very filling and obviously are sweet, so grab a cup of coffee for a perfect breakfast or snack.

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    I spy…a yummy donut!

  • Eventide Oyster Co: a Portland staple, this joint serves up dozens of different oysters from around the East Coast with interesting pairings like kimchi ice, pickled red onion, and cucumber ginger. Also makes a mean lobster eggs benedict. I personally didn’t care for the lobster roll here because the bun is soft and mushy much like what you’d expect on the bottom of a benedict. I prefer the toasted buttered roll for my lobster rolls!


Places on my to do list to try:

  • Fore Street: We made a reservation here but was sadly too full to make it. This is a sister restaurant of Street & Co and from what I’ve heard, it is the fancier branch. According to my friend Ashley, the tomato tart is to die for.
  • Duck Fat: everything and I mean everything is cooked in duck fat. What’s not to love? I wanted to try to poutine and the Belgian fries with creative dipping sauces.
  • Hugo’s: fine dining, $$$$ on yelp. One of our friends had the tasting menu here and said it was one of the best meals he has ever had.

What to do:

It was a very laidback weekend without a stressful rush to “see everything,” which I really liked. We spent a lot of time walking around downtown Portland and exploring its super cute restaurants and shops. We also had a car so we drove out to Fort William and Allagash Brewery Co. Those were both the high points of the trip! Fort William is a beautiful lighthouse / fort / park with the Bite of Maine lobster truck located in it, so you can eat your lobster roll while enjoying a gorgeous view. There were tons of families camped out having picnics on the lawn. I would have loved to sit out with a book and read there!

Beautiful Fort William, a great place to eat lobster rolls and walk around the park

Beautiful Fort William, a great place to eat lobster rolls and walk around the park

Walking around the cute cobblestone streets in downtown Portland

Walking around the cute cobblestone streets in downtown Portland

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Allagash Brewery Co. is a must visit if you like beer. The tours get booked up in advance so make sure to book yours on the website before you go. Anyone who visits gets a token to enjoy a complimentary flight of beers ranging from light to dark to specialty ales.

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Overall, relaxing weekend filled with delicious food. What more can a gal ask for? Happy end of summer!

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Click below for pieces (or something similar!) I was wearing in the pictures above.

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