When I started planning a weekend in Gloucester, Massachusetts, I knew I wanted that quintessential New England coastal experience, seafood, beautiful harbor views, historic charm and plenty of time near the water. What I didn’t realize was just how much we would be able to fit into one weekend.
Located about an hour north of Boston on Cape Ann, Gloucester is one of America’s most historic fishing communities. That connection to the sea is still very much alive. Fishing boats come and go from the working harbor, seafood dominates restaurant menus, and gorgeous ocean views seem to appear everywhere you turn. But one of the things that surprised me most was that Gloucester is about so much more than its fishing history.
Before we dive in, I am sharing our travel day to Gloucester photo album below. Here is how the first day went in our journey to this beautiful fisherman village.
Things to Do in Gloucester, MA
During our girls’ weekend, we went whale watching, explored a medieval-style castle museum overlooking the Atlantic, shopped downtown, learned about Gloucester’s haunted history and ate our fair share of oysters and seafood.
If you’re planning a New England getaway, here are my favorite things to do in Gloucester, MA, along with where we ate and the boutique hotel we called home for the weekend.
Go Whale Watching With Cape Ann Whale Watch
If you have time for only one big adventure while you’re in Gloucester, I would make it a whale watch. We headed out with Cape Ann Whale Watch, which departs from Gloucester and takes guests offshore in search of whales feeding in the waters off Massachusetts. Many who are in Boston, interested in Boston Massachusetts whale watching, end up in Gloucester since it is only an hour outside of the city and a much more calm and scenic starting port.
There is something completely different about seeing a whale in the wild compared with watching one on television. You find yourself staring across what seems like an endless stretch of ocean, waiting for the slightest sign of movement. Then suddenly, there it is.
During our trip, we had the extraordinary experience of watching two humpback whales traveling side by side for roughly 30 minutes.
We even watched them pec slap, a behavior in which whales slap their long pectoral fins against the surface of the water. Seeing these massive animals communicating and moving through the ocean together was easily one of the highlights of our entire weekend.
My tip: Bring layers even if the weather feels warm on land. It can feel much cooler once you’re out on the water. Sunglasses, sunscreen and motion-sickness medication if you’re prone to seasickness are also worth packing. Also, this tour has a cash bar for drinks and snacks so be sure to bring cash, because they do not accept credit card or any other form of payment.
Explore Hammond Castle Museum
Of all the things I expected to find along the Massachusetts coastline, a medieval-style castle was definitely not one of them. That’s part of what makes Hammond Castle Museum such an interesting place to visit.
The castle was built in the late 1920s by inventor John Hays Hammond Jr., a pioneer in radio-control technology. His incredible home overlooking Gloucester’s rocky coastline served as a residence and laboratory while also providing a place to display his collection of Roman, Medieval and Renaissance artifacts.
Walking through the museum almost feels like you’ve temporarily left Massachusetts. You’ll find dramatic stonework, a Great Hall, intricate architectural details, artifacts and an incredible courtyard that makes portions of the property feel centuries older than they actually are.
My favorite area was the indoor pool and garden. It felt incredibly serene, and it was one of those places where I wanted to slow down and simply take everything in.
Once you’ve finished exploring inside, make sure you spend some time outdoors as well. The Atlantic stretches beyond the castle’s coastline, creating a pretty spectacular backdrop.
One thing to know before visiting is that there are a lot of stairs. Hammond Castle Museum says navigating the galleries involves more than 160 steps across multiple levels, so keep that in mind if anyone in your group has mobility limitations. I’d also check the museum’s current hours, ticketing and parking information before your visit.
Shop Downtown Gloucester
Not every part of a weekend getaway needs to be scheduled. Leave yourself some time to wander through downtown Gloucester without much of a plan. Main Street and the surrounding downtown area are filled with locally owned boutiques, galleries, restaurants and cafes. We spent part of our weekend simply walking around, shopping and taking in the atmosphere.
I think these unstructured pockets of time are especially important when visiting a smaller town. They give you a chance to experience the destination rather than just moving from one attraction to the next.
Downtown also connects naturally with Gloucester’s HarborWalk, where granite story posts placed throughout the area share pieces of Gloucester’s history, culture, art and maritime heritage.
Take a Haunted Harbor Walk
If you know me, you know I love incorporating a little haunted history into a trip whenever I can. Our Haunted Harbor Walk ended up being such a fun way to experience another side of Gloucester.
Our guide, Aspen, shared stories tied to Gloucester’s long maritime history, including sailors, shipwrecks, mysterious happenings and some of the people who, according to local lore, may have never completely left.
Whether or not you believe in ghosts, I love tours like this because they make you look at a destination differently. Instead of simply walking past an old building, harbor or street, you start learning about the people who lived there and the stories that have been passed down through generations.
And if you’re planning a fall trip to Gloucester? A haunted walking tour just feels right.
Restaurants in Gloucester MA
You can’t visit one of America’s most famous fishing communities without making seafood a significant part of the weekend. Fortunately, Gloucester makes that incredibly easy.
We tried several restaurants during our trip, and each gave us a slightly different experience.
1606 Restaurant & Oyster Bar at Beauport Hotel
If you’re looking for happy hour with a view, 1606 Restaurant & Oyster Bar at Beauport Hotel Gloucester is a beautiful place to start. The hotel sits right along Gloucester Harbor, and the setting was exactly what I wanted from a coastal New England getaway. Grab a drink, order some oysters and enjoy the harbor views.
I especially loved that the setting felt unmistakably like Gloucester. Instead of feeling like you could be sitting in a restaurant anywhere, you can look outside and immediately be reminded that you’re spending the weekend in a historic coastal town.
I’d recommend stopping here for happy hour before dinner, although I could have easily stayed much longer simply enjoying the scenery.
Oak to Ember
For dinner, we also visited Oak to Ember, which offered something a little different from the traditional New England seafood experience. The restaurant focuses on live-fire cooking, incorporating wood-fired and smoked techniques into dishes featuring both seafood and meat.
After spending so much of the weekend immersed in Gloucester’s maritime culture, I liked having a dinner option that still felt connected to the destination without simply repeating the same traditional seafood menu.
Tonno Restaurant
Another Gloucester restaurant worth adding to your list is Tonno Restaurant. Tonno combines Italian cuisine with the incredible seafood available along the New England coast. You’ll find raw-bar selections and seafood alongside pasta and other Italian-inspired dishes.
During our trip, Tonno was also offering $1 oysters from 3 to 5 p.m., which made it a fantastic happy-hour stop.
If oysters are on your Gloucester agenda—and I think they should be—this is definitely a spot to check out. Just keep in mind that happy-hour promotions can change, so confirm the current special before you go.
Seaport Grille
If what you’re craving is that classic New England waterfront seafood dinner, Seaport Grille is the type of restaurant you’re probably picturing. Located along Gloucester Harbor, it pairs water views with a menu featuring New England seafood favorites as well as steaks, burgers and other American dishes.
For me, part of the fun of visiting a coastal town is having at least one meal where you can order seafood and a drink while watching boats move around the harbor. Seaport Grille checks that box.
Where to Stay in Gloucester, MA: The Highliner Hotel
For our girls’ weekend in Gloucester, we stayed at The Highliner Hotel, and it made a wonderful home base for our trip. When I’m only visiting a destination for a few days, location matters. I don’t want to spend a large portion of a short getaway driving back and forth between my hotel and everything I came to experience.
The Highliner’s location made it convenient for building out our Gloucester itinerary while still giving us the more intimate experience of staying at a boutique property. I also loved the hotel’s laid-back, modern coastal style. When I’m visiting a smaller seaside destination, I generally prefer accommodations that feel connected to the place rather than a hotel that could be located in any city.
And after a long day of exploring Gloucester, The Highliner was genuinely somewhere I looked forward to coming back to. It was cozy and chic, and there was something so nice about putting on The Highliner robe, climbing into the incredibly comfortable bed and relaxing after spending the entire day exploring. For a weekend trip, that’s exactly what I want from a hotel: a convenient location, plenty of comfort and a little personality.
How to Spend a Weekend in Gloucester, Massachusetts
If you’re trying to turn all of these recommendations into an actual itinerary, I wouldn’t overcomplicate it.
Spend one morning whale watching and leave the afternoon open for downtown Gloucester and shopping. Follow that with happy hour overlooking the harbor and dinner.
Use another day to visit Hammond Castle Museum, explore more of the coastline and enjoy another waterfront meal. Once the sun goes down, head out on the Haunted Harbor Walk.
Most importantly, leave yourself some unscheduled time. Part of what I enjoyed about Gloucester was simply being near the harbor, wandering through town and enjoying the slower pace that comes with a coastal New England getaway.
Is Gloucester, MA Worth Visiting?
For me, absolutely.
What surprised me most about our weekend in Gloucester was just how much variety we found in a relatively small destination. We headed out onto the Atlantic looking for whales, wandered through a castle museum, shopped downtown, listened to ghost stories, ate oysters and enjoyed dinners overlooking a working harbor—all during one getaway. But it never felt like we were simply checking attractions off a list.
Gloucester has a strong sense of place. Its maritime history isn’t something that exists only inside a museum. You see it in the boats moving through the harbor, taste it in the restaurants and hear it in the stories locals tell about their city.
That’s ultimately what made me enjoy Gloucester so much.
Cape Cod may get more attention when travelers start dreaming about a Massachusetts coastal vacation, but Gloucester offers its own distinctly New England experience.
If you’re looking for beautiful ocean scenery, incredible seafood, maritime history, unique things to do and enough variety to fill a girls’ trip, couples’ getaway or long weekend, Gloucester, Massachusetts, is absolutely worth adding to your New England travel list.
Please Note: I always strive to provide accurate and helpful information, but just a quick heads-up—I’m a blogger, not a doctor, lawyer, CPA, or any other kind of certified professional. I’m here to share my experiences and insights, but please make sure to use your own judgment and consult the right professionals when needed.
Also, I accept monetary compensation through affiliate links, advertising, guest posts, and sponsored partnerships on this site, however I am very particular about the products I endorse and only do so when I am truly a fan of the quality and result of the product.
