After our time in Bar Harbor came to an end, we road tripped down the coast to our final destination of Portland, Maine. Now – if you are making the scenic drive down the coast, a local friend of mine (Hi Grace!) suggested Red’s Eats as the #1 destination for lobster rolls. Taking one look at it, this ‘middle of nowhere’ dive spot in Wiscasset looks INCREDIBLE. Fairly sure they steam lobsters in front of you, and that is all I can want. Unfortunately, we could not stop, but as I have said throughout this post, I am leaving breadcrumbs to follow upon our return to Maine.
Portland is a coastal metropolitan city and bustling with young individuals and fantastic food. Think San Francisco & Seattle are having a baby, but not nearly as expensive. We were excited to explore when we arrived and started with well…lobster rolls. THERE’S A THEME HERE. But first, where did we stay?
Where We Stayed

Image by AirBnb
Our stay was at an incredibly generic hotel next to the airport (no photos to speak of) because I am not a morning person and our flight was at 7 am. However, I had my eye on a couple of fun places to stay closer to downtown and aesthetically beautiful. The Blind Tiger resembles something you would see in historic downtown Chicago and has elegant amenities. Breakfast is also included! The Westin Portland is centrally located downtown in the heart of the arts district. Finally, because you know I love me some AirBnb, the Skolfield Inn looks bright and spacious as well.
Where We Ate & Drank


#Lobsterrollgate2020 only continued when our first stop in Portland was the High Roller Lobster Company. High Roller was the most hyped of all the spots I researched before our trip and came highly recommended by a local friend. When we arrived, the waitlist stemmed over an hour, so we threw our names on the list and headed to walk around the downtown area. A mid-afternoon libation was just the ticket, and Blyth and Burrows supplied everything we needed. B&B’s signature cocktails were delicious (order the social picnicking, refreshing and not overpowering!). The gas-powered lamps and moody setting makes you feel like you are back in time.




After clocking back our cocktails with the unexpected “your table is ready” text, we headed to High Roller. Now, if you are traveling with someone that does not like lobster, take them here. Mark does not enjoy seafood and truly loved the lobster roll he ordered here (to my delight). The fun part of this spot is you can customize what is on your lobster rolls, such as specific types of butter and several types of ketchup (the curry ketchup is impressive). We promptly finished and headed to get donuts because…we’re on vacation? Want a heart attack?
Other lunch and dinner options suggested by locals: Duck Fat (duck fat fries), Eventide Oyster Company (the line can be INSANE but has some of the best oysters in town, head there early!), & Street & Co.


Holy Donut is a Portland treasure, and to be honest, I was skeptical at first. These donuts are famous in Maine and made with well…potatoes. It does not sound like it would be in any way acceptable, right? WRONG. They were ridiculous and tasted so delicious. The consistency of them is thick, almost making them a donut cake. Because we arrived late in the afternoon, some popular flavors were sold out. However, our favorite was the Dark Chocolate Sea Salt.
Other sweet treat & breakfast spots: Becky’s Diner (classic breakfast diner feel), Ri Ra (brunch) & Two Fat Cats Bakery.



Naturally, it was time to wash it all down with some local beer from Rising Tide Brewery. Portland certainly has a craft brewing culture and the outdoor (but cozy with heaters) setting was perfect for enjoying the end of a day of eating. We met up with a good friend of mine from college (whom I have referred to as my “local” in this guide!) and enjoyed catching up on current life. I ended up ordering some oysters because it was my moral imperative to at least have a dozen before we left Maine. A little taboo to order at a brewery, but the salty sea taste was exactly what I was hoping to accomplish.

The final pit stop was to a food truck adjacent to Portland Head lighthouse as the weather started to turn (clearly from the photo above). Bite Into Maine was hands down my favorite lobster roll (see best lobster roll post), and although freezing, we doubled up on lobster meat and enjoyed an unforgettable seafood extravaganza.
Portland Head Lighthouse




To a Californian like me, a coastal lighthouse is idealistically Maine. The Portland Head Lighthouse is along the Cape Elizabeth shores and is a beautiful place to watch the waves roll in. The lighthouse has been around for hundreds of years and stands as a landmark in the community. We walked around the grounds taking in the seascape, but not for as long as we hoped! Staying dry was not in our favor.
Maine was an absolute spectacle that I am elated to have had the opportunity to visit. Through the holidays and the new lockdowns in motion, I take a sappy moment to realize that these experiences are something not to take for granted. Our country is beautiful, and I cannot wait to explore more when the world gets a little safer.
Cheers,







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