Take the red line from Harvard Square to North Station, then transfer to the Newburyport/Rockport Line 113 towards Rockport and get off at Gloucester. In less than two hours, you’ll reach one of the best beach towns in Massachusetts! 

During my freshman fall, I was lucky enough to be paired with a roommate who became my best friend. After our first few weeks on campus together, Mila invited me to visit her hometown, Gloucester (pronounced “glost-er,” not “glouch-est-er”). We took the T, the subway, and then the commuter rail to this stunning coastal city.

Once we arrived, her parents treated us to delicious home-cooked meals, allowing us to take a much-needed break from dining hall food. Afterwards, Mila gave me a tour of the city. She showed me her favourite spots, including her old high school, local shops and the seaport. As someone who had lived there almost her whole life, she told me all about Gloucester’s rich maritime history and its annual festivities.

One notable landmark we visited was the Man at the Wheel, an iconic Gloucester Fisherman Memorial which serves as a tribute to the city’s seafaring history.

Mila also described two major summer festivals in Gloucester. The first, St. Peter’s Fiesta, held at the end of June, celebrates the city’s fishing heritage with live music, boat races, a carnival and a greasy pole contest! Last summer, my friends and I all went to the fiesta where we watched the Greasy Pole Contest live. We saw several candidates try to cross the pole attempting to capture a flag fixed at the end of the slippery pole. One by one, we watched contestants dive into the water until someone was able to complete the task. Experiencing this event with a crowd of locals and tourists was both thrilling and heartwarming, reflecting Gloucester’s vibrant community spirit.

At the end of the Summer, thousands of people gather for a Labor Day weekend tradition called the Gloucester Schooner Festival to celebrate the age of sail in Gloucester Harbor. Each year, schooners come to Gloucester to race. Many people ride the large boats, attend a boat tour and learn more about the history of these ships. While I haven’t had the chance to attend the Gloucester Schooner Festival, it’s definitely on my bucket list!

After our drive, Mila and I went to the beach. There are several beaches in Gloucester, but each one has its own charm. Whether you want to lay on the sand and read a book or swim in the water, you will find tranquillity amidst the beauty of the beach and the sounds of the waves.

Since my freshman fall, I have had the chance to visit Gloucester several times! Whether for Thanksgiving break, a beach trip or a weekend getaway, it is always refreshing to visit the coastal city.