You don’t hear of Gloucester, Massachusetts very often. Typically, you hear Boston or Cape Cod, so Gloucester falls into the well-forgotten category. This town offers history, adventures and stories waiting to be uncovered.
Keep reading to discover your next vacation and things to do the minute you arrive.
6 a.m. The Man at the Wheel
This iconic statue created by Leonard Craske in 1925 stands as the Fishman’s Memorial. “Man at the Wheel” shows a seaman clutching a ship’s wheel in order to fight the storm. The statue commemorates the death of thousands of seamen over time. Now the movie The Perfect Storm has a whole new meaning. You can find the statue located along the Harbor Walk. This presents a beautiful scene for any time, however, the sunrise overlooking the water creates the best start to a day. “I remember my dad running behind me as he let go of the back of my bike seat. Eventually, I freaked out and ran into the statue,” University of Central Florida sophomore Cade Kulak said. Not to mention, Harbor Walk creates a safe walking path perfect for learning how to ride a bike.
7 a.m. Stage Fort Park
This “small” park, that actually lasts miles long, marks the spot where the area was founded in the 1600s. If you follow the Harbor Walk, it leads you to this beautiful area called Stage Fort Park. You can’t miss the rock that stands 60 feet tall. The option befalls you to take a hike through the woods and go on an adventure in order to achieve the best view of Gloucester’s harbor. This rock became known as a ritual stone to the Native Americans, who placed cannons around the rock to protect from invasion. The more you explore Stage Fort Park, the more canons you find. Next, you approach the playground. Walking deeper into the park, you can see how the playground grows of age. Next, choose which direction you want to travel. Taking a hike leads you to the beach where Gloucester was founded, a rock with a fantastic view or the ocean, where you can sit on mountains of rocks that hover over the waves. Time to get your adventure on.
8 a.m. Hammond Castle
This Medieval-style castle, built by John Hays Hammond, is one of the most interesting yet creepiest parts of Gloucester. If you have no fear of an open jaw bridge or lion statues that watch you walk by as they guard the door, then go back in time and visit Hammond Castle. You can walk through the old castle and follow the path that leads to the gardens. Sight the moss growing up the stone walls and view the largest pipe organ in the world. “This cute mansion is very romantic and the perfect place for a date,” Faith Doucette said. This site considers itself a museum, however, the castle existed as a true living place for the high-class citizens. Visit the dungeon–if you dare.
9 a.m. Ravenswood Park
If you have a feeling for a little adventure, hopefully you can survive the woods. This park provides multiple trails to follow on a map. The Gloucester woods don’t compare to any ordinary woods. Let us just say, people like to leave their mark. As you travel through the fallen leaves, and hopefully you don’t trip over the trees roots that creep out of the ground, you find pieces of art. Some people leave carvings on trees and others use nature as a way to create their own. Ravenswood Park doesn’t just provide a place to walk, but there’s a place to ride your bike. At high speeds you can glide through the trees–just watch out so you don’t drive into a branch.
10 a.m. Cape Ann Lanes
In Gloucester, big ball bowling does not exist, only candlepin. Cape Ann Lanes provides the best bowling in town, not to mention the only bowling in town. The small balls make it easy to roll, and they feel lighter too so kids have more control. This means that the pins and the isles need to stay smaller to make the game more challenging. However, since 1959, it has provided the best friend and family fun. The food can actually come with high quality. Burgers come at a decent size with a great side of fries, but the lanes get recognized for the hot dogs and nachos. With arcade games and leagues, as well as beer and wine, Cape Ann Lanes offers a fun place to stay during the rainy days.
11 a.m. Ice Cream Trucks
Speaking of childhood memories, Gloucester continues to make these memories come true. On a casual day, you might hear music travel around you, but have no clue as to why. Well, ice cream trucks continue to live in this old town, so you get the chance to enjoy classic ice cream cones or ice cream sandwiches. You can buy anything from $0.75 to $1.25. Children and adults run outside to catch the truck every summer. “This is the one place you can find an ice cream truck nowadays. Remember when that was a thing,” said Chris Kulak. It roams the streets every day waiting for its next customer looking for an old fashioned treat.
12 p.m. Good Harbor
Good Harbor doesn’t necessarily give off the typical vacation beach vibe. After walking down the winding boardwalk, a beach full of adventure lies before you. The sound of crashing waves soothes you of all tension, while the smell of a salty breeze tickles the hairs in your nose. Great for all ages, Good Harbor Beach has classic volleyball nets for tournaments. Down on the east coast lies hermit crab island. Kids love hunting these down to catch them as their new friend. Just around the bend awaits shallow and calm waters perfect for younglings. It lowers just deep enough so teens can jump off the bridge for a little rush. “I love spending the day chilling by the sand with some friends,” Gloucester High School senior Julia Harrison said. However, when low tide hits, magic floats in the air. Down on the beach’s west coast, an underwater path begins to appear. Follow this sandbank path to the middle of the waters to discover an island–just make sure you make it back before high tide.
1 p.m. Whale Watch
Let your hair blow in the ocean winds as the taste of seawater mists your face. Captain Bill & Sons Whale Watch serves as a small family-owned whale watch company, where you can almost get crushed by a whale. Just kidding…maybe. On this four hour tour, take a ship out for an afternoon at sea. Make friends with the mammals of the sea and view these massive whales. They love to jump out of the water and play like a child, but others can seem a little shy. These tours never get old because you have a different experience every time you board the ship. Don’t forget your jacket–it gets a bit chilly out in the windy shore.
2 p.m. Quarries
Speaking of adventure, nothing gets you more excited than a little adrenaline boost. At the quarries, you can jump off cliffs of rocks into a deep bank of water. If you have no interest in risk-taking, you can just climb down the rocks and swim, but that seems kinda lame…don’t you think? “One of the best places to just get some alone time and hang out with my friends is by the rocks,” Gloucester local Colin Harrison said. If you don’t want to get your hair wet, fine. The top of the rocks provides a great view and a beautiful picnic spot. So get on your bathing suit and 1..2..3…JUMP!
3 p.m. Maritime Gloucester
Get ready to get up close and personal with some fish. Located on Gloucester’s historic harbor, the discovery center stays people friendly. Marine Life gives a new way of learning with a Sea Pocket Aquarium and an interactive touch tank. Rare sea creatures like the blue lobster, orange lobster, starfish and crabs can climb across your hand. You can also learn about the famous fish company history in the Gallery. This also contains historical artifacts, model boats, pictures and stories of Gloucester that give a little insight into what this fishy town represents. If you want to become a part of Gloucester, you need to know how to properly tie a few knots. Down by the pier you can learn a few of these while touring vintage boats.
4 pm. The Formidable
The Formidable is a rare siting in Gloucester, MA and if you happen to gain enough luck to see it, do it. This ship only shows up as a surprise for the locals every few years. Aye, a real pirate ship with ropes, ladders and planks. The Formidable tells wise tales after traveling around the sea. On this boat, you can tour the sea and light cannons toward threatening ships. You learn about Blackbeard, the Whydah and John King. You won’t watch the performance, but you will act a part of it. They teach you about the Boston Tea Party and important buildings all pirates should know about. After a day at sea, you might turn into the most well-trained pirate around.
5 p.m. Lobsta’ Land
A trip to Gloucester would not leave an impression without a true bite of Lobsta’. Off the bridge that connects Gloucester to the rest of Massachusetts, you see a little shack on the left. Lobsta’ Land became known for, well you could guess, lobsta’ and clam chowda’. With an incredible view of the marshes, you are surrounded by a Krusty Krab atmosphere. An old-time bar and restaurant serve the fisherman and old-time folks with a fun environment. Don’t get caught up in the ropes on your way in and watch the trap by your feet!
6 p.m. Nichols Candy
Walter and Margaret Nichols opened their first candy store in 1932 in Gloucester. They ended up traveling around MA realizing that Gloucester holds the place for them. Now after 74 years, this little candy shop stays a tradition. Here you can enjoy all the handmade candy you can find. Everything from chocolate lobsters to chocolate fudge and you can watch it all get made from the window inside the shop.
7 p.m. St. Peter’s Festival
Want to know a real party…aka FIESTA? During the last week of June, Gloucester celebrates St. Peter’s Festival. This five-day fiesta honors St. Peter, the patron saint of all fishermen with parades, loud live music, Seine boar races, a 5k race, a carnival and the famous Greasy Pole contest. Made of 40 feet of wood, this pole extends from a four-story platform rising above the waters. During the year it sits idle, waiting for the next contester. However, the Friday of St. Peter’s Fiesta crews slather the pole in Crisco, bacon fat and, of course, fish guts to make it a deathly match. Each competitor attempts to run across this pole in the fastest time possible to reach the flag that sits at the opposing end. The prize? Fame hard to fathom anywhere but here. The honored winner walks proudly through town with the flag followed behind him, so everyone knows who owns it.
8 p.m. Hockey
No matter what high school you go to, you will not find one without an ice rink. Hockey lives in the soul of the people in Gloucester. Every child played hockey like a boy plays football. Mini future Bruins walk the school. Living here, you have to know how to skate. Talbot Rink, home to the Gloucester High Fisherman Boys hockey team, located at O’Maley School, supplies skates and a layout to start learning. Food concession opens during games but not during the day. Of course, high school rinks will charge you for access, so they do not supply food all the time. Unfortunately, if you want classes you need to hire a personal trainer. Or you could just learn that falling on your tailbone does not give a very pleasant feeling.
9 p.m. Main Street
Time to take a stroll down Main Street. Nowadays. Little streets like this get hard to find. Toy Shops, boutiques, shoe stores, bakeries and classic restaurants create the perfect place for shoppers. Main Street gives the ‘small town’ feeling you have been searching for. Home of beautiful shops, all family-owned, and where kids can freely stroll down the sidewalk with their red balloon. The most popular restaurant on this street? The Franklin. With quality food such as Chicken Alfredo and desserts such as Chocolate Mousse, you can’t go wrong.
10 p.m. Cape Ann Brewery
Visiting Gloucester without having a drink? Impossible. The awarding-winning, family-owned Cape Ann Brewing Company features crafted beers brewed on-site. For example, one of the most popular beers called “Fisherman’s Brew” represents the Gloucester flavor. Feeling like you want to sit drinking on the port side of a ship? Check out the wooden tables and rocking chairs that create the old bar laidback scenery. Classic bar games like pool, ring on a string and ball in a cup stay open to play at your own stress level. The best thing about this place? They provide free popcorn.
11 p.m. Rocky Neck
Calling all artists or art admirers: Time to explore this hidden gem. Artists thrive here at Rocky Neck with gallery after gallery. From pottery to photographers, paintings to sculptures and the home to many beautiful restaurants, Rocky Neck shows the creative side of Gloucester. If you do not possess the skills of an artist by any measure, but you want to attempt to create something of your own, art classes of any kind wait for you here. Commoners love Rocky Neck, not only for the art but also for the food. With a line of galleries, comes a line of restaurants and bars. If celebrating a birthday, start at Main Street and work your way to Rocky Neck. Let’s see how far you can go. Also, the restaurants make it very convenient to enjoy a meal. Why you ask? After a long day of fishing, people can easily guide their boat to park at a dock and grab a drink.
12 a.m. Gloucester Cinema
Time to go back in time a few years and visit an old-style movie theater. The tickets stay cheap, and the screen stays scratched. However, with a group of friends it makes the best hangout spot on any given night. Get your old fashioned popcorn from the workers who dress up as Josh Peck and sit down in that old squishy chair. You really get the childhood feeling from the ’90s.
1 a.m. Dogtown Common
The complicated history of DogTown extends to the colonial days of New England. Early settlers attempted to farm on Gloucester’s land. They quickly realized fishing was more efFISHent. (Ha. Ha.) So, the rich community moved to the shore and DogTown caught its name with the roaming dogs of the neighborhood. Here in Gloucester, it remains a park that was once deserted land. Eventually, the place became deserted and Mr. Babson, one of the original landers, enjoyed the land as a spiritual getaway by carving his viewpoints on nature itself. To this day you can still see his ideas on the large boulders.
2 a.m. Ten Pound Lighthouse
Watch the colors of the sky blend like ink into the clouds from the best in Gloucester. The boat usually leaves around 2 A.M. and will not leave till 10 A.M. The Ten Pound Lighthouse stays in sight from many viewpoints along Gloucester’s waterfront, but to actually stand there feels completely different. On an island only accessible by a private boat stands a lighthouse. An island of rocks gives the perfect romantic getaway. It secures the Gloucestermen’s safety as they turn back and see the light to follow home.
3 a.m. Halibut Point’s Stacked Rocks
Here at Halibut Point lies paths and picnic tables that sit by the ocean. However, people like to jazz it up a bit. To make this place unique, people take creativity into their own hands. On big mountains of rocks, people find the small ones and stack them to make a small balanced sculpture. Of course, I cannot tell you exactly where it lies, it would ruin the adventure of finding it. Thousands of stacked rocks create a landmark art piece. So, start finding little rocks and leave your mark by the ocean.
4 a.m. Beauport Hotel
Located with a view of Gloucester Harbor, you do not have to stay at the Beauport Hotel to enjoy the fancy amenities. A seasonal rooftop pool and bar open to the public gives a friendly environment to hang out with friends. Sometimes the nights get chilly so you can enjoy the outdoor firepits while watching the lighthouse spin. Locals love to sit up and day drink while watching the boat people enjoy the day. At night, you can watch the lighthouse light spin across the water.
5 a.m. A Day at Sea
A local’s best day is spent on the sea. Almost everyone owns a boat, and if they don’t, they have a friend who owns a boat. You can drive all around Gloucester, literally, on your boat in a day. If you feel worried about food, have no fear! Restaurants fill the area where you can pull up and grab a bite. Family’s love taking the boat out to sandbanks and even the greasy pole to get some practice in before the big day. Driving around all day can be a little boring, so you need some action time as well. This brings fishing into the equation. Here we do not do any ordinary fishing, we go deep-sea fishing. This early in the morning is when all the fish are out and about. If you are a true fisher you won’t be coming home till late at night. If that feels a bit too much, just set up a few lobster traps and go on your way. Anyone who lives in Gloucester turns into a true fisherman.
