TRAVEL // Road Trip to Portland, Maine

Portland, Maine

Yup, I’m at it again. Another road trip in the books! This time, the destination: Portland, Maine. Before embarking on this trip, I must warn you – there are many lessons on this journey. Let’s start with Lesson #1: there is NO avoiding every living soul who will need you to clarify that you’re talking about Portland, Maine and NOT Portland, Oregon. Goodness gracious, Portlandia, look what you’ve done! But, don’t worry, Maine. We gotchu – we know you came first! ;)

Jokes aside, with an itch to travel, my coworker and I packed our bags with no itinerary in mind to explore this coastal town. We rented a car from JFK, made a pit-stop in Boston and arrived in Portland… nine hours later… which brings us to Lesson #2: Google Maps lies. D:< Though we anticipated a long drive, we ran into major traffic in Massachusetts and took 1.5 hrs longer than our expected 5.5-hr drive. Yup, so after a full day of practically driving, we called it a night.

With only one full day to spend in Portland, we got an early start and decided to make the most of it. Luckily, the forecast was clear despite the heavy rain during our drive. Our first stop: J’s Oysters. The restaurant had an indoor and outdoor area, right by the water, with a scenic Portland view and pleasant ocean breezes.

Portland, Maine

J's Oysters @ Portland, Maine

Man, Lesson #3: you have not tasted real, fresh seafood until you have come to Portland, Maine. For real. I got some delicious baked oysters and crab-filled mushrooms cleverly served in an escargot dish. My coworker got a half-dozen oysters along with her lobster, both incredibly fresh. The lobster was so fresh, in fact, that very little to no condiments were needed to appreciate the flavor.

With a great brunch to start off the day, we eagerly explored the quaint Old Port area, walked through an interesting art fair and visited the Portland Museum of Art. Lesson #4: fine arts and crafts are a biiig deal here. Though the collection at the Portland Museum of Art was very small compared to NY standards, there were many galleries to stop by and a relatively large Arts district.

Portland, Maine Portland, Maine

We walked and walked, and walked, and walked. By the time 5 o’clock came around, we were starved! Luckily, without booking a reservation far in advance, Street & Co. starts accepting walk-ins at 5pm. Perfect timing. (Lesson #5: Book your restaurant reservations at least a month prior to arrival for more well-known restaurants.)

Portland, Maine

It’s super easy to miss the restaurant as you’re passing by. We found it hidden in an alleyway, only noticeable by the growing number of people starting to wait at the door. To be honest, we were only here for one reason. We needed to try the infamous lobster diavolo for two… And, that we did.

Street & Co @ Portland, Maine

Look at it! This monster of a dish had two perfectly cooked lobsters on top of pasta in a ciopinno-like sauce. Oh my goodness… I am still dreaming about the lobster diavolo.

There were a selection of fresh oysters ready to order, decorating the counter that we sat at. We enjoyed an exceptional salad and decadent bourbon pecan pie to end an extremely satisfying dinner.

Street & Co @ Portland, Maine

We literally thought nothing would be able to top off this experience. I mean, I would come back to Portland just to go to Street & Co. again. It makes me extremely curious to try their sister farm-to-table restaurant Fore Street, which requires reservations far in advance.

With bellies full, I reluctantly suggested that we fit one more attraction to our trip before calling it a night. We simply couldn’t leave Maine without having seen a lighthouse. It’s just necessary. The weird thing was… every time we looked up attractions in Portland, the top destinations oddly did not include a lighthouse. Super confusing. Luckily, I remembered seeing a postcard that said Portland Head Light, so that’s where we decided to go.  Little did we know, the best part of our trip was yet to come…

Portland, Maine

Even as we were driving up to the Portland Head Light, it already was beautiful with the sun setting in the background. We quickly rushed to go watch the sun set, fill the clean ocean air into our lungs and take in the most breathtaking view of the lighthouse.

Portland Head Light, Maine

Portland, Maine

Lesson #6: Absolutely make sure that Portland Head Light is in your list of things to do. Seriously. It bums me out to know that we could have missed out on such a gorgeous view if we weren’t so determined to find a lighthouse. With bellies AND hearts content, we made our way to our AirBnB to rest before our long drive.

The next day, we were back on the road and ready to hit up another lunch spot, recommended by another coworker. We found ourselves in a cute little town called Kennebunk, a 30-min drive from Portland. There were a ton of galleries in the town center with plenty of gift shops and boutiques.

Kennebunk, MaineKennebunk, Maine

Kennebunk, Maine

Kennebunk, Maine

The main attraction, however, was this AMAZING lobster roll from The Clam Shack.  You can ask for the roll with butter or mayonnaise. Unlike most places, they did not overdo the butter/mayo and let the true flavor of fresh lobster speak for itself. Holy moly, it was perfect.

The Crab Shack @ Kennebunk, Maine

And, it was the perfect ending to a fun-filled and food-filled weekend. Last lesson of my trip: in my next go around, I definitely would want to take more days off to spend in Boston so that the majority of the trip was not committed to driving. Regardless, I can’t wait to be back!

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