There are so many charming small towns and cities scattered throughout Massachusetts. Gloucester, MA is one of these destinations worth visiting when you’re in the Bay State for stunning views, outdoor activities, and memorable dining experiences. As you can see, when you spend time at this quaint seaport town on Cape Ann, there’s far from a shortage of fun to be had and places to explore. If you’re curious to know more, read on to learn about things to do when you’re in Gloucester.

Located on the North Shore of Massachusetts, the small seaside city of Gloucester has so much to offer residents and visitors alike. Between its coastal beauty, lighthouses, and restaurants that serve fresh seafood, this town in Massachusetts is an ideal destination for a staycation, or weekend away. It’s also known to be one of the popular day trips in MA from Boston too.

Paul Keleher from Mass, US/Wikimedia Commons This coastal community also offers so much more including a few places you may not have thought about visiting here. Let’s take a look…

  1. Hike to an abandoned town.

Di M/TripAdvisor One of the many things to do in Gloucester is to visit Dogtown Common. This site is an abandoned settlement that was first settled in 1693. It was chosen by settlers due to its location inland and its rocky terrain which they thought would protect them from pirates and natives. By 1830, the area was abandoned and is now part of the Essex National Heritage Area.

David Bruce/Flickr Take a hike around the stunning woodlands and you will see numerous boulders with inspirational words etched onto them. These were part of a public art project commissioned by Roger Babson, founder of Babson College, during the Great Depression. Dogtown is quite the hidden gem in Gloucester. You can read more about it in this piece about Gloucester, MA . Dogtown Commons, Gloucester, MA 01930, USA

  1. Visit a castle.

Hammond Castle Museum/Facebook Who would have guessed a European castle could be found in Gloucester, MA? Hammond Castle was built atop a bluff overlooking the ocean in the 1920s by John Hays Hammond, Jr., a scientist, inventor, and art collector.

Hammond Castle Museum/Facebook A visit to this medieval-style castle may make you feel as though you’ve been transported to the European countryside. Self-guided tours of the lavish interior decorated with fine art and antique furniture are available on certain days from April through December. The grounds are quite extraordinary to explore as well. Hence, this makes for one of the most memorable day trips in MA. Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA

  1. Dine on Portuguese food.

Azorean Restaurant & Bar/Google While mostly known for its many fresh seafood restaurants, Gloucester, MA is also home to a fantastic Portuguese restaurant called Azorean Restaurant & Bar. The owners are from the Azorean island of Sao Miguel and proudly serve authentic Portuguese cuisine. Even the decor inside this warm and inviting eatery is reminiscent of what you may find in Portugal.

Azorean Restaurant/Facebook The menu is filled with delicious options like Portuguese soup, Portuguese-style mussels, octopus, grilled linguica, carne guizada, and fresh fish. You’ll also find a variety of American dishes on the menu. End your day exploring one of the most charming towns in MA by dining at this special restaurant. Azorean Restaurant & Bar, 133 Washington St, Gloucester, MA 01930, USA

You’ve just learned about a few of the top places to visit when you’re in Gloucester, MA. Take a look at things to do in Gloucester to discover more about one of the most popular towns in MA for a day trip.

Paul Keleher from Mass, US/Wikimedia Commons

This coastal community also offers so much more including a few places you may not have thought about visiting here. Let’s take a look…

Di M/TripAdvisor

One of the many things to do in Gloucester is to visit Dogtown Common. This site is an abandoned settlement that was first settled in 1693. It was chosen by settlers due to its location inland and its rocky terrain which they thought would protect them from pirates and natives. By 1830, the area was abandoned and is now part of the Essex National Heritage Area.

David Bruce/Flickr

Take a hike around the stunning woodlands and you will see numerous boulders with inspirational words etched onto them. These were part of a public art project commissioned by Roger Babson, founder of Babson College, during the Great Depression. Dogtown is quite the hidden gem in Gloucester. You can read more about it in this piece about Gloucester, MA .

Dogtown Commons, Gloucester, MA 01930, USA

Hammond Castle Museum/Facebook

Who would have guessed a European castle could be found in Gloucester, MA? Hammond Castle was built atop a bluff overlooking the ocean in the 1920s by John Hays Hammond, Jr., a scientist, inventor, and art collector.

A visit to this medieval-style castle may make you feel as though you’ve been transported to the European countryside. Self-guided tours of the lavish interior decorated with fine art and antique furniture are available on certain days from April through December. The grounds are quite extraordinary to explore as well. Hence, this makes for one of the most memorable day trips in MA.

Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA

Azorean Restaurant & Bar/Google

While mostly known for its many fresh seafood restaurants, Gloucester, MA is also home to a fantastic Portuguese restaurant called Azorean Restaurant & Bar. The owners are from the Azorean island of Sao Miguel and proudly serve authentic Portuguese cuisine. Even the decor inside this warm and inviting eatery is reminiscent of what you may find in Portugal.

Azorean Restaurant/Facebook

The menu is filled with delicious options like Portuguese soup, Portuguese-style mussels, octopus, grilled linguica, carne guizada, and fresh fish. You’ll also find a variety of American dishes on the menu. End your day exploring one of the most charming towns in MA by dining at this special restaurant.

Azorean Restaurant & Bar, 133 Washington St, Gloucester, MA 01930, USA

What are some of your favorite things to do in Gloucester, Massachusetts? Tell us in the following comments section.

OnlyInYourState may earn compensation through affiliate links in this article.

The OIYS Visitor Center

Gloucester, MA January 28, 2023 Marla S. What are some popular family-friendly day trips in MA?  Along with spending the day in Gloucester, take a look at the following family-friendly day trips in MA too.

Visit the Mass MoCA in North Adams. As the largest space in the country for visual and performing arts, there’s something for everyone. Spend the day playing at Bancroft Tower in Worcester. Here, you can explore the castle, play in the snow, or take a hike around this hidden gem in MA. Take a day trip to Provincetown and relax by the beach, shop till you drop, and grab a bite to eat too.

  For more ideas of where to go, take a look at these day trips in MA too   What are some towns in MA along Cape Ann?  In addition to Gloucester, MA, here are some towns along Cape Ann:

Essex: Known as the best town for antiquing in the Bay State. Manchester-by-the-Sea: Home to Singing Beach - one of the best spots in the state. Rockport: A quaint town with lots of shops to explore. Ipswich: Along with being home to Crane Beach, it’s a scenic day trip

  Follow this road trip throughout Cape Ann if you’d like to spend the day (or weekend) exploring these towns in MA.  

The OIYS Visitor Center

Gloucester, MA

January 28, 2023

Marla S.

What are some popular family-friendly day trips in MA?  Along with spending the day in Gloucester, take a look at the following family-friendly day trips in MA too.

Visit the Mass MoCA in North Adams. As the largest space in the country for visual and performing arts, there’s something for everyone. Spend the day playing at Bancroft Tower in Worcester. Here, you can explore the castle, play in the snow, or take a hike around this hidden gem in MA. Take a day trip to Provincetown and relax by the beach, shop till you drop, and grab a bite to eat too.

  For more ideas of where to go, take a look at these day trips in MA too   What are some towns in MA along Cape Ann?  In addition to Gloucester, MA, here are some towns along Cape Ann:

Essex: Known as the best town for antiquing in the Bay State. Manchester-by-the-Sea: Home to Singing Beach - one of the best spots in the state. Rockport: A quaint town with lots of shops to explore. Ipswich: Along with being home to Crane Beach, it’s a scenic day trip

  Follow this road trip throughout Cape Ann if you’d like to spend the day (or weekend) exploring these towns in MA.  

The OIYS Visitor Center

The OIYS Visitor Center

Along with spending the day in Gloucester, take a look at the following family-friendly day trips in MA too.

  • Visit the Mass MoCA in North Adams. As the largest space in the country for visual and performing arts, there’s something for everyone.
  • Spend the day playing at Bancroft Tower in Worcester. Here, you can explore the castle, play in the snow, or take a hike around this hidden gem in MA.
  • Take a day trip to Provincetown and relax by the beach, shop till you drop, and grab a bite to eat too.

 

For more ideas of where to go, take a look at these day trips in MA too

What are some towns in MA along Cape Ann? 

In addition to Gloucester, MA, here are some towns along Cape Ann:

  • Essex: Known as the best town for antiquing in the Bay State.
  • Manchester-by-the-Sea: Home to Singing Beach - one of the best spots in the state.
  • Rockport: A quaint town with lots of shops to explore.
  • Ipswich: Along with being home to Crane Beach, it’s a scenic day trip

Follow this road trip throughout Cape Ann if you’d like to spend the day (or weekend) exploring these towns in MA.