Boasting a 400-year history and holding the title of American’s oldest seaport, Gloucester, MA is a part of New England that should absolutely be on your list. So why, as a born and raised New Englander had I never visited until this year? Maybe it’s because I grew up summering on Cape Cod or that I lived in Boston for 7 years, but for some reason heading to the North Shore never really crossed my mind as a place to go for a trip. However, when a close friend booked his wedding at a new boutique hotel in Gloucester, I jumped at the opportunity for a weekend trip to this coastal town! Only an hour from Boston and completely accessible via public transportation, Gloucester is a perfect (and super easy) weekend getaway for city dwellers or travelers visiting Bean Town. Keep scrolling to read my Gloucester weekend guide for that perfect escape from Boston you’ve been looking for!
What to Do in Gloucester, MA:
Take a stroll down the HarborWalk
For beautiful views of the Gloucester Harbor, make your way to the Gloucester HarborWalk. This waterfront path is pedestrian, roller-blader, and cyclist friendly, and is the perfect spot for an afternoon stroll or ride.
On this path, you’ll find signs highlighting this fishing port’s history and will pass the esteemed Fisherman’s Memorial which memorializes the thousands of fishermen lost at sea in the first three centuries of Gloucester’s history.
You’ll also cross Blynman’s Canal which is where you can see the tuna boats go by (like the ones you may have seen in National Geographic’s show, Wicked Tuna)!
The walk is pretty short and will take you about 40 minutes roundtrip from Beauport Hotel (which is where I stayed) and even less by bike. I borrowed a sweet beach cruiser from Beauport Hotel and cruised all the way down to Half Moon Beach, which takes us to our next activity in my Gloucester weekend guide!
Relax at Half Moon Beach
You never know what the weather is going to be like in New England, but if you luck out as I did, make sure to make your way to Half Moon Beach and relax on this sandy cove for an afternoon.
I went in the fall, so there was virtually no one else there, but during summer months I assume it’s quite crowded! You can ride your bike here, but there will be a few parts where you’ll need to walk it, as there is no smooth path to ride along.
Go on a Whale Watch
I’ve had the privilege to go on quite a few whale watches in my day. (Check out the one I just went on in Quebec!) I would absolutely recommend it as a top activity to do when visiting this part of the country, as it is truly spectacular to see whales in their natural habitat!
Although I didn’t have time to go on one during my visit to Gloucester, I would recommend checking out Cape Ann Whale Watch to book your trip. They guarantee whale sightings for every whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of Gloucester. It’s deemed one of the “Top 5 Whale Watching Destinations in the World” by the World Wildlife Fund due to the wide variety of whale species who migrate to the coast of Gloucester every year to feed on the abundant natural resources. (NOTE: Although the photo above was not taken by me, I have literally witnessed this in real life while on a whale watch off the coast of Massachusetts! It’s mind-blowing!)
Have a craft beer at Cape Ann Brewing Co
Similar to trying local food, I love to try local beer wherever I go and that’s why visiting a Brewpub made it into the Gloucester weekend guide! Cape Ann Brewing Co is on a mission to create a brand that exemplifies the grit and courage of the North Atlantic Fishing fleet, and with beers like “Fisherman’s Brew” and “Second Mate” I think they’re doing it right!
I tried the Beauport Pale Ale (named after the hotel I stayed at!) and it was excellent. They also offer outdoor harbor-side seating where you can watch the local fishing boats come and go.
Go shopping in Downtown Gloucester
Downtown Gloucester is a charming area full of historic buildings, bookstores, cafes, boutiques, second-hand shops and there’s even some street art to see! You won’t want to miss it, so make sure to carve out some time to check out this part of town.
If you follow me on Instagram or read my recent post about thrift shopping in Montreal, then you know that I absolutely love the thrill of thrift shopping, and this Gloucester weekend guide wouldn’t be complete without mentioning it! So if you’re a thrifting/consigning lover like me, you’ll want to stroll down Main Street and check out The Dress Code, a funky consignment shop where I found an adorable skirt for $3!
Where to Eat in Gloucester, MA:
Sandpiper Bakery
This quaint little bakery tucked down a side street in downtown Gloucester offers an amazing selection of homemade baked goods – think pumpkin bars, croissants, tarts, cookies of all kinds – you name it, Sandpiper Bakery makes it! It’s a great place for breakfast, but I ended up stopping by for lunch where I enjoyed a ham & fennel sandwich on freshly baked ciabatta bread. It was so good that I still dream about it to this day. I also tried their homemade mint lemonade which was just as good, and if I had gone earlier in the day I would have ordered a coffee which they source from local roasters in the area.
1606 Restaurant
Located within Beauport Hotel, this sophisticated restaurant & bar has become a favorite in the area not only to visitors but also to the locals. The design is very upscale-nautical, with decor details that celebrate the life of a fisherman, like black & white photographs of sailboats and fishermen from many moons ago, leather studded chairs and booths, and a model sailboat dominating the center of the restaurant.
I can imagine prominent sea captains back in the 1600s coming here after months out at sea for a scotch. (My imagination, I know.) I absolutely loved the floor-to-ceiling windows exposing the Atlantic Ocean ahead where patrons can watch the boats coming and going from the Gloucester Harbor. 1606 Restaurant is known for serving up New England style favorites like clam chowder, fried seafood, and local oysters. It was my birthday when I visited and the staff brought me a beautiful dessert and even sang me happy birthday!!! Thank you to my server Maggie and hostess Hayley for making my birthday so special!
Seaport Grille
This is the sister restaurant to the 1606 Restaurant at Beauport Hotel, so you know it’s going to be a quality experience. The restaurant was packed when I arrived at 6:30 pm which is always a good sign. I really enjoyed the harbor views from my table and found the restaurant decor so charming and the ambiance very inviting. From twinkle lights covering the outdoor patio ceiling to a massive anchor shaped beer tap, Seaport Grille’s decor was very creative & nautical in an understated way.
As for the food, I was recommended the cioppino spicy tomato seafood stew (which looked fabulous – a table near me ordered it) but I went for a classic New England meal of a clam chowder and their famous fish and chips and was not disappointed! They’re also known for their award-winning seafood platters and have some interesting options like Mexican-style haddock.
Where to Stay in Gloucester, MA:
Beauport Hotel
If you’re looking for coastal elegance in a luxurious seaside boutique hotel, then look no further than the waterfront Beauport Hotel. They graciously hosted me for a night and I was beyond impressed by the design, amenities, location, the incredibly hospitable staff, and my personal favorite – the rooftop pool.
They took classic, quintessential New England design and added a modern flair to create a cozy and coastal-chic ambiance to fall in love with. I don’t know if it’s just because I’m a Massachusetts girl, but I felt so at home here while still feeling the luxe-modern elegance of a boutique hotel. Some of my favorite details were the Cape Cod style shingles on the exterior, the chic lantern style lighting, and all of the nautical touches found throughout the hotel.
My Room:
And speaking of details, no element was overlooked when designing their classic American cottage themed accommodations. With details like nautical hooks as drawer handles, to a “No Wake Zone” sign instead of a “Do Not Disturb” sign, these creative details added that extra element of thoughtfulness.
I stayed in Suite 235, an Ocean Front Jr King Suite with a private balcony and direct views of the Atlantic Ocean and Gloucester Harbor. I was told that this room boasts the best view in the entire property and I don’t think they were lying!
My absolute favorite part of staying in this suite was falling asleep and waking up to the sound of crashing waves onto the shore just outside of my window. There are very few things in life that bring me as much peace as the sound of ocean waves.
In the morning I put on the cozy robe from the closet, made myself a cup of coffee, and relaxed out on my private balcony for a while as I watched seagulls fly over the bay and beachgoers hunt for sea glass and shells along the shore. This is my definition of bliss.
Birds Eye Rooftop Pool Deck & Bar
I was amazed by the roof deck at Beauport Hotel. In fact, there were a few times where I looked around and forgot that I was in Massachusetts!
It almost felt like I could have been somewhere on the Mediterranean, but with a New England style twist. The Birds Eye Rooftop Pool Deck & Bar features a heated pool, jacuzzi spa, serviced bar, and the best part – 360 views of the Atlantic Ocean, Gloucester’s working seaport, and the city skyline. PROTIP: Head up around 5 pm to catch the sunset when other guests are heading down to get ready for dinner or a wedding held at the hotel!
Note that this uber relaxing and luxurious experience is only available to overnight guests, but I think after reading this post you will want to stay for at least a few nights anyway.🙂 If you’re not able to stay overnight, you can still enjoy a cocktail and beautiful views from the 1606 Restaurant waterfront patio.
How to Get to Gloucester, MA (From Boston)
By Car:
By car, it’s an easy 1-hour drive from downtown Boston, but there’s usually traffic so make sure to factor that in! You can easily rent a car from Logan Airport and zip north for this weekend getaway!
By Commuter Rail (Public Transport)
No car? No problem! The MBTA commuter rail will take you directly to Gloucester! All you have to do is take the commuter rail from North Station on the Rockport Line. It costs $10.50 each way and takes about an hour.
Make sure to get off at the Gloucester stop. From there it’s only about a 10-minute walk to Beauport Hotel or downtown Gloucester. Make sure to check the daily schedule to confirm departures. It’s perfect for both travelers visiting Boston who want to see more of Coastal New England and Bostonians looking for a weekend getaway without needing a car.
I hope you enjoyed my Gloucester weekend guide! Comment below if you’ve been or want to visit this New England gem!
Looking for another getaway in Massachusetts? Next check out A Perfect Weekend in the Berkshires: What to Do & Where to Stay!
Disclaimer: I received a complimentary stay and some meals mentioned in this post in exchange for my opinions, but all opinions are my own. I only recommend places that I love!
Wander On,
Wanderluluu xx
