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America’s Oldest Seaport


Pavilion Beach


The whipping Massachusetts Bay winds caught us off guard as we settled into our seemingly assigned park bench. The October Thursday sun had just begun to set and the temperature got noticeably cooler. By now, the families with energetic little children and sprinting dogs playing fetch had gone home. This left just my boyfriend, Mark, and I and a few fellow couples who wanted to enjoy a relaxing evening at the park by the ocean in the picturesque city of Gloucester.


The strong gusts stripped Mark of his prized cherry-red Patriots baseball cap. Usually, he would hustle after it and make sure it was back in his possession if it ever flew off. This time, however, he knew it was safe. Nobody around us would have stolen it and it had acres and acres of grassy park to gently land on, at some point. We didn’t mind chasing after it. Nobody there was going to judge us and it made us feel young again.


Since Mark and I have returned back to college in nearby Beverly, we make it a point to drive the 25 minutes to Gloucester at least once a week. A few places we frequent are historic Stage Fort Park, Captain Solomon Jacobs Park next to the Coast Guard and a strip of local shops on Main Street. Exit 14 on Route 128 takes you to all of these places. We know the route by heart now!


Before September of 2020, I had never visited Gloucester before. I had no idea what to expect and I didn’t know what to expect. In early September, Mark and I decided to go to Stage Fort Park on a really nice day. It was breathtaking, to say the least. The ocean breeze was refreshing, the laughter from the children warmed our hearts and the seagulls flying overhead made us feel safe. We stayed until sunset, talking for hours about whatever couples talk about. We took an extreme amount of pictures because the sunset that evening was gorgeous and vibrant. Ever since that evening, Gloucester has had our hearts.


Sitting at the park bench, Mark moved in closer to me and said, “I love spending time together”. He was looking out toward the opposite side of the ocean when he turned to me, lovingly, saying, “I have a feeling I’m going to fall more in love with you each time we go.”



My boyfriend, Mark, and I


For our one-year anniversary the following week, we decided to try out the HarborWalk, a self-guided walking tour along the fishing port. The tour features 42 informational granite posts throughout the walk that tells you the stories of Gloucester’s mariners, artists, innovators, and interesting characters. They also include aspects of Gloucester’s history as a seaport, their rich culture and community and how they are evolving to a modern, sustainable fishing industry. Both of us learned so much about the city’s history and why it’s such a special place. One marker that stuck with me was the second post (we didn’t go in order) which featured famous poet T.S. Eliot. I learned that Eliot used to vacation at Eastern Point when he was a boy and wrote “Four Quartets”, his Nobel Prize-winning poem in 1948, after his fascination with the mariners he worked with when he was learning how to sail.


For Columbus Day weekend, Mark and I decided to check out Main Street after hearing about a place called Castaways Vintage Cafe. I had been following them on Instagram for some time and was intrigued by their vibe. We walked down the bright blue steps into the shop from the sidewalk and I was enamored. The floor is covered in clothing racks filled with vintage and thrifted tops, bottoms and jackets. There is a corner of the shop with a cafe that serves smoothies, coffee, acai bowls and more. There is also an outdoor seating area that featured $5 clothing racks as a holiday special. I managed to score a trendy Calvin Klein cropped and bleach dyed sweatshirt.


The owner of Castaways, Bianca Giacalone, opened the cafe just last year and was hit hard by the initial outbreak of Covid-19 back in March. She said that business finally started booming again once they opened back up for good in May.


“People didn’t forget about us,” said Bianca. “We have a unique thing going on at our shop and they couldn’t wait to come back. That makes me feel good.”


Anywhere you walk in Gloucester, you will see blue utility pole banners that read “GLOUCESTER 400 – 1623-2023”. You can’t miss them. Gloucester is commemorating their 400th anniversary in three years and is already starting the celebration. On the bottom of the sign, you will see a website URL: “gloucesterma400.org”. If you visit this website, you will see a countdown clock ticking down to 2023 and see that they are sharing stories of Gloucester’s notable community members and encourage other residents to share theirs, too. This can be done through the website via writing, video or audio.


Being founded in 1623, Gloucester predates both Salem (1626) and Boston (1630). Gloucester is most well-known for its fishing ports and extensive fishing history. There are a plethora of seafood restaurants scattered about the city and any of them are well worth the trip. As a shrimp aficionado like myself, the very best shrimp I have ever eaten came from Causeway Restaurant, a reasonably priced local favorite situated across the road from a marina.


Gloucester plays a huge role in the fishing industry not just in New England but the United States and has since its founding almost four centuries ago. In 2008, Gloucester was 10th in the nation among commercial fishing ports in volume of fisheries landings by weight (120.2 million pounds). It was also 9th in the value of landings ($54.2 million). Because of a significant downward trend in total New England groundfish landings, while Gloucester’s landings have remained stable, Gloucester’s importance as a groundfish port has increased considerably since the early 2000s.


Just a couple hundred feet east from Stage Fort Park sits the Gloucester Fishermen’s Wives Memorial. Built in 1925, this famous monument of a mother with her child looking for her husband at sea is a tribute to the thousands to the 10,000 Gloucester fishermen who have lost their lives at sea over the centuries. It also serves as a reminder that fishing is the country’s most dangerous occupation.


It’s not difficult to tell just by wandering around the city of Gloucester that it’s special. When you’re in Gloucester, it feels like you’re in another country. You forget that you’re in Massachusetts, on the North Shore, just 45 miles outside of Boston. And this is a good thing. It is the perfect place to simply escape for a few hours. There is so much to see, do and experience in general that you forget where you are for a while. As an anxious person, any time I am in an unfamiliar place, I will have my phone out and on the entire time, with Google Maps on my screen to make sure I don’t get lost and get into a bad part of town. When I’m in Gloucester, my phone stays in my pocket pretty much the entire time. I feel safe and wherever I end up, if I’m not actively seeking out a specific location, it could turn out to be a new favorite spot of mine. This is the mindset I have each time Mark and I venture over there. Every time we go, we find either a new spot to sit and relax, a new local shop or a new neighborhood street to gaze at the tight knit, brightly colored strung along the road. The adventure never ends and I am constantly looking forward to our next drive east.



Solomon Jacobs Public Landing

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