Maine, Day 4 - Beautiful Coastline Views, Freeport, and Portland

Updated: Nov 4, 2020

(Day 1, Day 2, Day 3, Day 5)


With three days in Maine under our belt, we were becoming seasoned professionals at eating lobster rolls, exploring the beautiful outdoor scenery, and finding amazing harbor towns across the coast. We had a big day ahead of us so we jumped right into it.


Yelena did some hardcore research (i.e., went on Google) and read about the Giant's Stairs Trail on Bailey Island. We decided that had to be our first destination of the day, so we jumped in the car and made our way over the Bailey Island Cribstone Bridge, which is famous for its novel design. We arrived at Giant's Stairs and walked out to the rocks overlooking the water. Believe me when I say, the Giant's Stairs Trail is even more beautiful in person than in pictures. There is something very magical about the rocky coastline and how the seawater from Casco Bay crashes into the craggy shoreline. The trail that hugs the rocky coastline isn’t very long and we were able to walk it in short order.

Thoroughly awed and still in the midst of a subjective phenomenologically profound state of mind, we proceeded to drive back through Bailey Island to the southernmost tip to get to Land’s End. Once you’ve arrived, you can see the Atlantic Ocean stretch out for thousands of miles before you on Bailey Island Beach and admire the natural beauty of the area. There is a famous statue of a Maine lobsterman overlooking the beach and a world-famous gift store named, obviously, the Land’s End Gift Shop, which has every type of Maine-related trinket and souvenir you could want. Yelena and I always get one Christmas tree ornament and one other souvenir from every place we visit, so we walked out of there with a red lobster ornament and a magnet.


From Bailey Island, we drove to Freeport, which hosts the famous L.L. Bean flagship store, many other retail shops, and a park about five minutes from the downtown area. We were told by multiple locals to visit the L.L. Bean flagship store, so we traipsed through the sprawling retail location. The store even has its own lobster roll place called Linda Bean’s Perfect Maine Lobster Roll, where you can refuel while shopping. After exploring the downtown area, we made our way to Scarborough Beach State Park, so we could check off one of Maine’s famous beaches off of the list.

Kicking it by the boot

Scarborough Beach stretches out pretty far when it’s low tide, so we were able to freely wheel around the area. When it’s clear, you can see a few small islands out in the water. The beach is constantly changing due to the very high and low tides, as well as the strong currents in the water. We saw a couple of surfers out in the water and Yelena sadly forbade me from surfing with them as 1) I can’t surf; and 2) it was very cold.

Scarborough Beach

After the beach, we packed ourselves into the car and scooted along to Two Lights State Park in Cape Elizabeth, which is right where the Atlantic Ocean and Casco Bay meet. We easily found parking and walked out to the rocky outcrop, where we could see the beautiful shore and lighthouses. The walk is very scenic and the lighthouses have a very interesting history - these were the first twin lighthouses in Maine. One is still in operation today while the other is now a private home.

Two Lights State Park

After fully wearing ourselves out, we headed back to the Airbnb to wash the sea salt from our hair and get ready for dinner. We decided on Eventide, which is famous for having the best lobster roll in Portland and the wait times reflect that. Yelena went ahead to grab us a reservation two hours beforehand, while I stayed in to do some work for a couple of hours. All of a sudden I received a frantic call that it was time to meet for food and our table would only be held for 15 minutes. I quickly ordered an Uber and was on my way. While waiting at a stoplight a couple of blocks from Eventide, my Uber driver commented to me “wow, that girl must be really late to something” about a person sprinting across the road with two boxes of food in her hand. That person was Yelena. It turned out that she had ordered appetizers at a different restaurant not realizing the time, so we ate her appetizers together on a bench while we waited a minute to be sat for our actual meal.


Eventide truly had one of the best lobster rolls in Portland. The bun is steamed rather than toasted and the brown buttered lobster tastes even better than you can imagine. We had to get the lobster corn salad dish as well as a regular salad to be ostensibly healthy. After bursting at the seams with lobster, we walked around Portland at night and took in the city before heading back to the Airbnb to get much-needed rest.

(To be continued on Day 5...)


Most importantly, don't forget to see the world, and eat the food.


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