5 Things To Do In Gloucester in the Fall 

October 03, 2023 / Things to Do & See

Gloucester, Massachusetts is known as a summertime destination for its beautiful beaches and harbor, amazing restaurants, and cultural events. But did you know that there’s plenty to do and see during the fall months when the bulk of the tourists have headed home and the city tends to quiet just a bit? 

Autumn in Gloucester is just as spectacular in its offerings as it is during the peak summer months. The cultural and art events, walking and hiking trails, maritime history, and even some water activities are still ongoing during this time of year when the weather tends to be very cooperative. 

Here are five of our top picks for exploring and enjoying Gloucester this fall. 

Cape Ann Plein Air Competition

Photo by Lorne Bell 2017

Attend the Cape Ann Plein Air Competition 

If you love art or can at least appreciate the craft, visiting Gloucester and Cape Ann during the annual Cape Ann Plein Air competition is a must-attend event.

The Cape Ann Plein Air competition is New England’s premier outdoor painting competition held annually. This year during the seven days from October 8 – 15, 2023, visitors can walk the coastline and scenic vistas to watch art in action. The communities of Gloucester, Rockport, Essex, Manchester-by-the-Sea, and Ipswich will see up to 38 of the finest artists in the nation compete for over $20,000 in prizes and awards. 

The presence of these artists and the competition itself are also meant to raise awareness of the importance of plein air painting and raise the visibility of the creative economy on Cape Ann, the birthplace of American plein air painting. 

The artwork produced will be sold at the Grand Awards Gala on Saturday, October 14, 2023 and the sale will continue until Sunday at 3 pm.

Take a Leaf-Peeping Hike 

Fall is a wonderful time of year to get outdoors and connect with nature. Not only is the humidity often low and the temperature mild, but the trees are bursting with color and putting on a show of their own. 

Take yourself on a leaf-peeping hike in one of Gloucester’s many wooded trails. One of our favorites is Ravenswood Park off Route 127. Here you can get your heart pumping on ten miles of crushed-stone carriage paths or take a meandering stroll to enjoy the solitude of the woods. There is even a child-friendly, two-mile Ledge Hill Trail that will take you among the magical-looking, fern-covered boulders. Visitors should definitely make sure to trek to the overlook of Gloucester Harbor. It is spectacular any time of year! 

Learn About Cape Ann & Gloucester’s History 

Fall is the perfect time of year to visit one of the many places on Cape Ann where adults and youngsters alike can learn a little something about the history of the region. 

To learn about Gloucester’s maritime heritage and the sea life beneath the surface, we suggest starting your museum tours at Maritime Gloucester, found along Gloucester’s working harbor on Harbor Loop. Explore the Maritime Science Education Center and the indoor aquarium during the cooler months where you and your family can learn more about seafaring, ocean life, and the regional history of the fishing industry. 

If the weather is cooperative, take a walk on the 200ft pier that extends into Gloucester Harbor where you can watch the boats and witness several schooners at dock! Don’t forget to visit the museum store and its unique selection of gifts, books, toys, and clothing for kids and adults.

From there, take a walk downtown to visit the Cape Ann Museum where you can learn more about the art and cultural history of maritime New England. 

If medieval architecture and scenic views are on your list of things to see and do, take a tour of Hammond Castle Museum where you can see the home and laboratory of one of the nation’s most prolific inventors and collectors of antiquities. Hammond Castle Museum offers Spirituality and Candlelight Tours in the fall months, and has several fall events and workshops running, like Psychic Exploration & Spirit Mediumship, Return to the Renaissance, and Tarot in Two Hours. 

Go on  a Whale Watching Trip or Deep Sea Fishing Expedition 

Getting out on the water isn’t just a summertime activity in Gloucester. Most vessels continue sailing through October. Enjoy a day of whale watching with one of Gloucester’s two Whale Watches(7 Seas Whale Watch and Cape Ann Whale Watch) and several Fishing & Sea Excursion Charter businesses.  

Be sure to call ahead and confirm trip hours and to reserve your tickets. 

Get Some Retail Therapy 

If shopping is the way you like to spend your time, Downtown Gloucester is a great place to start your retail therapy journey. 

If you can’t find the gift, clothing, shoes, or specialty item you desire there, head to Gloucester’s Rocky Neck neighborhood where you will find stores with handmade art in all different mediums. What’s better than getting a jump start on your holiday shopping and finding a one-of-a-kind piece for your family or friends? 

Don’t forget while you work up an appetite shopping to visit one of the many area restaurants that will have you returning over and over again with their unique and delicious cuisine.