Photo Diary | Portland, Maine


I spent time in Northeast Harbor, Maine almost ten years ago now, one summer in college, and fell completely in love with the area. I had actually never been to Portland though so when it was thrown out as a location for our girls trip I jumped on it and luckily the rest of the group agreed. It is the perfect long weekend spot. A super easy flight from most of the east coast and just enough to do around the city to fully relax while seeing/doing a lot around town.

I arrived in Portland late Thursday night and was able to squeeze in some champagne and dinner right next to our rental at Otto pizza with one of my friends. It was the perfect casual spot to start the weekend.


The remainder of our crew arrived late Thursday and early Friday morning(after a flight mishap ;) so we grabbed breakfast at Rosemont Market, bagels croissants and a few cookies too and made our way to the boat docks.


Our boat ride could not have been more amazing. We debated on doing a morning or sunset boat ride but really the morning turned out perfect. We had breakfast and mimosas on the boat– it was the perfect start to our trip!







The views along the water just can’t be beat. If you’re able to get out on a boat, or even the ferry, I highly recommend it. We past lobster boats, kids sailing camps, seals and got to see some really gorgeous homes on the harbor! The company we used actually rents the boat on AirBnB too and does overnight sailing trips which I’m sure would be amazing on some of the smaller islands.




After our sailing adventure we went back into town and had locals beers at East Ender and a late lunch at Duckfat. I cannot recommend the duckfat fries and original milkshake enough. So simple but so delicious! Duckfat is a sister restaurant to Hugo’s, a local  farm to table staple, if you’re looking for a nice dinner - we didn’t try it but I’ve heard great things.

From here we walked around town, did a little window shopping and ended our evening at Eventide Oyster Co. for dinner. It’s a must if you’re in the area. Order some raw oysters (or fried if raw isn’t your thing) and do not miss the brown butter lobster roll in a steamed bun – amazing! Not too buttery to overshadow the lobster, just enough flavor to knock your socks off. We debated ordering a second round J Instead of we opted for a homemade coconut choco taco and ice cream sandwich and were not disappointed.


Saturday morning we grabbed coffee and potato donuts at Holy Donut. It was our first experience with Maine potato donuts, made from mashed potatoes not potato flour, and they were amazing! Some of my favorite donuts I’ve ever had. Don’t miss the Maine blueberry, fresh lemon, chocolate sea salt and Maine coffee brandy. We tried a few more(big eaters here!), but those were our favorites.





After donuts we made our way down to Cape Elizabeth to work off our breakfast. We walked along the rocky shore stopping what seemed like every 5 steps for photos and eventually made our way to the Portland Head light. It was a gorgeous morning and a quintessential Maine walk!



On our way home we stopped at the Lobster Shack (waited in the forever long line) and grabbed fresh lobster rolls, local beers and sat by the rocks and enjoyed one of my favorite meals of the trip. While this place is definitely crowded it’s worth it for a good fresh roll and the atmosphere sitting right along the water.


A must on my Maine list is ice cream from Mt. Desert Island Ice Cream. It was a small spot only in Bar Harbor when I lived in Maine and it was my absolute favorite. So when I saw they expanded to have a shop in Portland I knew it was a must. I highly recommend the Jack Daniels, Toasted Coconut and Madagascar Vanilla!

Saturday evening we ventured to Central Provisions. I read a lot about this small spot before our trip and a friend actually had what she described as “the best burger of her life” there on Thursday before the rest of us arrived so I was excited to say the least. We all shared small plates including, fresh halibut, an amazing cobb salad with candied bacon, steamed clams, fresh bread and butter with a poached egg and a few other delicious treats. Overall each plate was simple, fresh and delicious. We finished our night with champagne at the bar and it was perfect!


On Sunday before we left we grabbed breakfast from Standard Baking Co. ate on the ferry and made our way to Peaks Island.


We attempted to rent two tandem bikes and failed miserably (there’s a great video of our attempt though!) before deciding single bikes were best for our group! We rode the four mile loop around the island stopping at every turn to take pictures and take in the scenery.



We made a pit stop for a glass of 50 cent pink lemonade from the cutest roadside stand. They snapped a picture of the four of us too!






It was gorgeous, a highlight of our weekend! I would definitely recommend bringing a great picnic next time and finding a good spot on the rocks to sit and enjoy.




We grabbed one more lobster roll, a blueberry beer and I was off to the airport. As I write this I’m realizing how much we fit into our weekend, yet it still felt very relaxing. I’m always sad to leave these trips but it also makes me even more excited for next year! Moral of the story – go to Maine, it’s amazing!

- Heath

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