Gloucester, Cape Ann, MA

Solo Travel for Introverts Ratings

Sensory Calm  5 out of 5 stars (5 / 5) – Goucester is the very definition of an introvert-friendly getaway. The small quaint storefronts and the quiet waves of the waterfront create an atmosphere of quietness and calm.

Solo-Friendliness 4 out of 5 stars (4 / 5) – Although Cape Ann is known for being a getaway for wealthy couples and families, I was pleasantly surprised at the solo-friendliness of Gloucester. Most restaurants had bar side seating and, outside, there were several benches to sit on and enjoy a snack.

Commute Friendly  3 out of 5 stars (3 / 5) –  While the East Coast has trains and buses, they become more and more of a rarity as you go up north. However, this town had a lot of free parking spots right by downtown, so if you have a car, commute is easy.

Predictability 5 out of 5 stars (5 / 5) – Very predictable. A regular American beachside place with an arsty vibe.

Safety  5 out of 5 stars (5 / 5) – Highly safe. Little to no crime, and a typically progressive Massachusetts town.

Nerdy stuff4 out of 5 stars (4 / 5) – The Cape Ann Museum is a major pull here displaying the place’s maritime history, along with several out of town attractions like Hammond Castle and other historic mansions. The downtown has a few art galleries and bookstores too.

What, Where & How

Gloucester is the first European harbor-town within the United States. It gets its name from the city of Goucester in South-Western England. The English settlement was made here in early 1600s at the time of Agawam Native-American people, and became the governors’ seat for the Massachusetts Colony, which would later move south into a newer city – Salem, and much later into the even newer city, Boston. But Gloucester was where it all began and the oldest of the three.

Boston is the nearest big city and the busiest airport, and renting a car from airport, one can easily drive here within an hour. While Cape Ann is expensive, one can find more affordable choices for accommodation anywhere in the greater Boston area.

I recommend this as a day-trip from Boston, Providence or Salem.


Goucester has a large crisp waterfront, in the shape of a crescent. There is a long walk and green spaces where many people jog or walk their dogs.

I found plenty of benches and I decided to sit down with an ice-cream and take in the view of yachts and sailboats in the sea – their pointy masts dotting the horizon and the cottage inns with gardens lined up along the land.

There is a beautiful memorial at the center of the waterfront memorializing the centuries of fishermen who never returned from the sea. Accompanying it, are related memorials, such as one remembering the widows and orphans of such fishermen who lost their lives.

It was refreshing to see, in a home of old-world wealth and illustrated historic figures, memorials to the common people, who have built this country and are otherwise pushed to the backgrounds of history.

Strolling across the Downtown

The small downtown of Gloucester is a delight to explore. Every single building has character and every turn and angle is photogenic. I walked along many quaint bookshops, art galleries, studios, small village pubs and cafes.

There are historic buildings and small museum houses at every turn, and many old commercial buildings are now repurposed into craft-stores, boutique hotels and restaurants.

It felt like this was a tiny English coastal town that floated across the Atlantic and attached itself to North America. Due the Covid-19 international restrictions, I had to cancel my trip to the UK, but this idyllic part of New England has had me convinced that there are similar quirky historic towns in the US too.

Cape Ann Museum

The Cape Ann museum was founded in late 1800s. While it has many exhibits of famous paintings inspired by scenes of Cape Ann, I only had a few minutes before the museum closed, and hence, decided to focus my time on the fishing history of this region instead. The museum has a lot of information that pertain to the early days of the region as an English colony, a diorama of the first seaport, as well as the signature redcoat uniform of the British Empire officers.

I also learned a lot about the technical details of early fishing vessels called American Schooners, and the history of mackerel farming with real examples of giant vessels stretching across hallways, and giant fishing nets hanging over ceilings.

There was also a lot of information about materials suitable for making strong fishing nets which are resistant to longterm exposure to water.

My favorite exhibit of all, was the giant lenses and mirrors used for lighthouses. The Fresnel lens was invented in the early 1820s by French physicist Augustine-Jean Fresnel. His design concentrated light to cast a beam which could be seen at a much greater distance than other lenses of that era.

The one in the picture was taller than a human being, and being in the presence of these giant glass structures which refracted light, casting rays of rainbow through them was a hypnotic experience. Highly recommended!

While exiting the museum, you can take a picture of “Cassie” – the East Coast’s version of the Loch Ness monster, which is rumored to be seen in Maine by several fishermen.

Stores & Restaurants

Walking through the main street, I found several charming storefronts lined up. My favorite was Dogtown Books which is a used-book store.

It looked unassuming from the outside, but inside, it not only had books, but also, centuries old print publications, large encyclopedias and maps which can be rolled out on a table and giant globes. It looked like a library out of some fantasy, with the sweet scent of old brown pages in the air. I also found several books on history, fishing and ecology of the Cape Ann area.

For food, my first choice was Turner’s seafood which looks like a pretty fish-and-chips shop from the UK. Dover sole was their speciality.

But alas, when I walked in, I realized it was a fishmonger and deli, and not a restaurant. There was excellent ready-to-eat food available, but the only seating area was two rickety tables outside, wobbling about in the chilly autumn winds from the sea, like bare trees at the end of their life. I decided to turn away and find a new place to eat.

While there were great sushi, poke and ice-cream places around, the cold fall season and the harsh winds from the evening sea made me crave for hot food. I decided to enter Topside Grill, and seated myself at the bar. I was a bit nervous at first, because it looked like an upscale place with suited waiters, but soon found the bartender super-friendly and he even offered to recharge my phone if needed. Most patrons at the tables, being locals, greeted each other jovially with loud cheers ringing across the room.

I was extremely impressed by the food. I had ordered a mixed seafood casserole, which contained generous helpings of scallops, white-fish and shrimp with a light dressing of cheese and cracker crumbs on top. The side, which was generally mashed potatoes, was replaced with squash for the fall season, and it was steaming, buttery and cozy.

Other Attractions

Two of the major attractions in this area are Castle Hill on Crane Estate and Hammond Castle Museum – two giant estates with castle and garden tours available – which were built by American tycoons as a slice of medieval Europe brought these shores.

Hammond Castle
Castle Grounds

I visited the Hammond Castle and it was a memorable experience. It deserves its own separate article and I will put it up soon.

Leave a Reply