32 Fun Things to do in Gloucester

April 06, 2021 / Art and Music, Food and Drink, Good to Know, History/Maritime, Outdoor Adventures, Things to Do & See

Excerpt from 32 Fun Things to Do Blog | Written by Addison Choate

With the anticipation of the warmer weather on the horizon, you may be thinking of planning a day trip or a longer stay to visit Cape Ann this Spring or Summer. No matter what time of year it is, our friends at Addison Choate have compiled 32 fun things to do in Gloucester, Massachusetts.

Here are 10 of the 32 fun and safe activities and destinations to discover in our historic seaport city. Read the full article at https://addisonchoate.com/32-things-to-do-in-gloucester/.


So, we think a logical place to start a discussion about things to do in Gloucester, MA is to talk about its incredible beaches. Gloucester is home to some world class beaches that are truly some of the best in New England. One of our favorite Gloucester beaches is Good Harbor Beach.

With beautiful soft white sand, a large area to spread out, incredible views of the Thacher Island lighthouse, and the ability to walk out to Salt Island during low tide, Good Harbor is a fantastic spot to spend a Summer day.

In the off-season you can still enjoy the beach and even bring your dog out for a run to burn off some of that extra energy. To learn more about Good Harbor you can read our Definitive Guide To Good Harbor Beach


Take a step back in time and set sail out of Gloucester Harbor aboard the 65-foot Schooner Lannon. Get a feel for what life was like aboard this authentic fishing schooner. You can even book a private charter or have a wedding aboard the ship!

The striking schooner was built in 1997 in Essex, MA. Framed with local white oak and black locust, the schooner has a length on deck of 64.5 ft and overall length of 90 ft.

The Schooner Lannon offers a variety of food options as well as beer, wine and other drinks to enjoy during the sail. It’s a fantastic way to get a different look at Gloucester harbor.


Gloucester is a working fishing port and home to some of the freshest seafood that you can buy. Whether you are looking for some fresh lobster, cod, tuna, or stuffed quahogs Gloucester has you covered!

A few of our favorite local shops include:

Connolly Seafood: http://www.steveconnollyseafood.com/
Captain Joe & Sons Lobster: http://www.wholesalelobster.com/
Turners Seafood: https://www.turners-seafood.com/gloucester-market/


We miss record shops. The process of finding the perfect album or discovering a hidden gem and the tangible community experience. And, if you think we are the same people that still like actual books better than e-books, consider us guilty as charged.

If you’re looking to take a step back in time and find the perfect record or that CD that you used to love you have to take a trip over to Mystery Train Records.

Located right on Main Street in Gloucester, Mystery Train has a great selection of rare & collectible vinyl from just about any genre you can imagine. Heck, they even have eight track tapes!

If you’re up in Gloucester, it’s definitely worth a stop!


Speaking of actual books, Gloucester has some incredible independent bookstores where you can peruse the stacks and find some incredible beach reading. A couple of stores that we love are Dogtown Books and The Bookstore of Gloucester.

Dogtown Books offers a wide selection of preowned books, certified pre-owned books, and just general used books to choose from. They topics range from culinary adventures to space exploration and the owners are very friendly and welcoming.

The Bookstore of Gloucester on the other hand has been serving Cape Ann readers for over 45 years and offers the perfect local alternative to Amazon. It’s a great spot to pick up the latest releases and browse the curated collection.

If you are interested in Independent Bookstores take a closer look at our article on 5 Great Independent Bookstores on Cape Ann.


If you are a fan of history and architecture, you have to make a point to stop at Gloucester’s Hammond Castle. Constructed by the eccentric inventor John Hays Hammond in the 1920’s, Hammond Castle serves as a beautiful showcase for Hammond’s impressive collection of Roman, Medieval, and Renaissance artifacts.

John Hays Hammond was a legendary inventor, holder of over 400 patents and is known as “The Father of Remote Control.” Visitors can tour the courtyard, great halls, secret passageways and war room and marvel at the beauty of the castle grounds.

In October, Hammond Castle even gets in the Halloween spirit with special haunted tours. If you fall in love with the castle you can even decide to host your wedding on site! It’s such a cool venue that it made our list of the Top 5 Gloucester MA Wedding Venues.


Cape Ann has no shortage of lighthouses and one of the best around has to be the Eastern Point lighthouse. This iconic lighthouse was originally built back in 1832 and reconstructed a couple of times.

The current 36-foot tower was built in 1890 and has an attached 2 story keepers quarters. Eastern Point You will see images of Eastern Point in publications about Gloucester and the lighthouse was even home to Winslow Homer back in 1880.

You can drive out to the light, park and take the half mile walk out on the dog bar breakwater to the Dog Bar Lighthouse. It’s a beautiful area and a great spot for a sunset or sunrise. If you want to see some incredible footage of the lighthouse you have to check out this Kenny Chesney video that was shot in Gloucester


What better way to explore the coastal cuisine of Gloucester, Massachusetts than on a foodie tour! Try a little bit of everything and learn about some of Gloucester’s hidden gems on the Cape Ann Foodie Tour.

From thick and tasty claim chowder to homemade olive oil and delicious Italian sandwiches, Cape Ann Foodie tour will expose you to the culinary delights of the area.

Learn more about their schedule and some of the stops here – Cape Ann Foodie Tours


Perched on a ledge overlooking Gloucester Harbor is the home of one of America’s first interior designers, Henry Davis Sleeper. Beauport, the Sleeper-McCann House, was Sleeper’s summer retreat and the 40 room mansion houses Sleeper’s diverse collection of folk art, pottery, antiques and other artifacts.

A National Historic Landmark, each room is distinguished by a historical or literary figure and no two rooms are the same. The property even features a beautiful garden and a secret staircase. The Sleeper McCann House is open from late May to Mid-October and is definitely one of the best things to do in Gloucester.


Dogtown Common provides hikers with an incredible 3,600 acres of mysterious woods, large boulders and carved stone to explore. Originally settled back in 1693, settlers chose the location due to its rocky inland landscape that offered protection from pirates and combative natives. The settlement was abandoned back in the early 19th century and has not been inhabited since.


With some incredible trails, Dogtown offers a great opportunity for hiking, biking, running, cross country skiing and an outing with your fur-friend. Along the paths you will find large boulders with sayings carved into them. These boulders were carved by unemployed Finnish quarrymen during the Great Depression who were commissioned by local entrepreneur Roger Babson.  There are 36 boulders that were carved with inspirational sayings such as “Never Try Never Win” and “When Work Stops Values Decay.” 

The name Dogtown is said to date back to the American Revolution and is derived from the dogs that the women kept while their husbands fought in the war. At one point it was estimated that there were anywhere from 60 to 80 homes in the area.  But after the war, the ports became safer, the fishing industry returned and so too did the settlers to the coastline. 

So if you’re in the mood for a journey off the beaten path, Dogtown is a great thing to do in Gloucester. Here is a link to a great Dogtown Guide