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Things To Do In Rockport MA On A Rainy Day

10 Things To Do In Rockport, MA On A Rainy Day | The Ultimate Guide

Summer 2023 was a wet one in Rockport, Massachusetts. Actually, that doesn’t fairly characterize the drenching we received on Cape Ann this year. With over 20 inches of rain in the Greater Boston area (the second rainiest on record) there were dreary days where we had delusions of an ark floating around Thacher Island. Take us away Noah!

Here at Addison Choate, we are definite heliophiles, but this summer has inspired us to provide a guide on things to do on a rainy day in Rockport, MA. So, without further ado, here at 10 Things To Do in Rockport, MA On A Rainy Day.


Take A Rainy Stroll Down Bearskin Neck

A rainy day can be a refreshing reset from time to time that washes everything clean and provides a fresh start. But with rain on 2/3 of our summer weekends, our perspective may have warped from a jovial Gene Kelly in Singin’ in the Rain to more of a dystopian Malcolm McDowell in A Clockwork Orange.

But a nice stroll down Rockport’s Bearskin Neck is sure to help lift your spirits. With a great variety of shops including art galleries, vintage candy shops, clothing stores, jewelry and more, you will definitely find the retail therapy you seek.

Perhaps, more importantly, you will find some kind and interesting shop owners who will be happy to discuss their artwork, wares and maybe even tell you an interesting tale or two.

Take some time to run into a local coffee shop, like Bean & Leaf for a hot coffee beverage and a pastry. Their seven-layer bars are sure to provide a nice pick me up. Then you can pop into My Place By The Sea, at the end of the neck or Fleur Cuisine on T-Wharf for a hot cup of chowder and lunch with a view. 


Visit The Rockport Art Association Museum

The casual visitor may walk past this old colonial home at 12 main street in Rockport, Massachusetts, but this building is not just another beautiful, historic Rockport home. The Association, formed back in 1921, is one of the oldest and most active art associations in the United States.

The museum is much larger than it looks from the outside with a beautiful gallery space in back. With a membership of hundreds of artists, the association puts on a variety of exhibits, demonstrations, classes, and lectures. A tour of the museum will provide the casual visitor a greater appreciation of life in Rockport and across Cape Ann. It’s truly the perfect thing to do in Rockport, MA on a rainy day.


Enjoy A Delicious Coffee and Tasty Donut at Brother’s Brew

If you need to warm up and take a little break from the rain, be sure to pop into Brother’s Brew Café.

Located right at 27 Main Street, just up the hill from the Rockport Art Association, Brothers serves up some fresh baked donuts, muffins, pastry, and a variety of sandwiches. They also have a full coffee bar to keep you caffeinated. A key to any rainy day!

Brothers Brew Rockport MA

But, make no mistake about it, the donuts are the star of the show at Brother’s Brew. This place is a Homer Simpson dream factory. Mmmmmmm donuts…..They always have a fantastic variety ranging from classic cake donuts (love, love, love) to the lighter yeast donuts. They also have some fun with festive holiday designs for different seasons and special occasions.


Take In A Show At Shalin Liu Performance Center

We are so lucky to have such a world class performance center right in the heart of our small coastal village. The Shalin Liu, with 330 seats, provides the perfect night out with an opportunity to have an intimate connection with some incredibly talented musicians.

Opened in 2010, the Shalin Liu, is truly a cultural hub for the Greater Boston area. The space is stunning with a floor to ceiling glass backdrop overlooking the ocean, and the acoustics are symphony hall caliber.

The Rockport Music team curates an incredible list of musicians that run the gambit of musical genres including classical, jazz, blues, Celtic, and everything in between. Hey, we even got to see Kevin Bacon perform this year, pretty wild!

Some memorable artists who have graced the stage at Shalin Liu include Dave Brubeck, Chris Botti, Bela Fleck, Chick Corea, Natalie Merchant, John Scofield, Marc Cohn, Bobby McFerrin & many more.

If you are looking for something to do on a rainy day in Rockport, we would absolutely put Shalin Liu at the top of your list!


Cape Ann Foodie Tours

We believe that one of the best ways to experience a destination is through its cuisine and Cape Ann Foodie Tours is a fantastic way to experience a wide variety of cuisine on Cape Ann.

Run by Gloucester local, Cindy Hendrickson, the Cape Ann Foodie Tours are a great way to experience the local cuisine and learn a bit about the history of Cape Ann. The tours last about 3 hours and since you will be in and out of restaurants and shops it is a great way to spend a rainy day.

On their Ales & Tales tours you can experience a local brew and be regaled with stories from local fishing captains. From legendary storms to run ins with Russian vessels and even Coast Guard rescues, learn more about the life at sea for Cape Ann fishermen.


Beauport Sleeper-McAnn House

What better way to pass a rainy day the touring a 40 room, 14,000 square foot home that was built by one of America’s first professional interior designers.

This National Historic Landmark was the summer home of Henry Davis Sleeper situated in a beautiful Gloucester neighborhood and perched on a ledge above the harbor, Sleeper certainly picked a fantastic lot to build his summer sanctuary.

Beauport Sleeper Mccann House Gloucester

Each room is uniquely designed, and you half expect that you will need to uncover who killed Mrs. White in the library with a candlestick. The Sleeper-McAnn House is open from May 24th to October 14th and is another fantastic way to spend a rainy day when visiting Rockport.


Visit The Local Cape Ann Bookstores

Cape Ann is home to a number of fantastic independent bookshops.  And, what better activity on a rainy day that perusing the stacks of your local bookstore to find your next literary adventure.

In Rockport, you will find the smallest and most adorable of the bunch, Susie’s Stories out on Bearskin Neck. Rockport is also home to another vintage bookstore on Main Street called Bullseye Flyboys. You are certain to find some unique offerings in this shop.

Rockport MA Bookstores

Other great stores that we highly recommend visiting include Dogtown Books in Gloucester, Manchester By The Book in Manchester By The Sea and The Bookstore of Gloucester.


Hammond Castle Museum

A medieval style castle right here on Cape Ann? In the words of Brian Kelly, yes it’s true. What better place to be on a moody, rainy day than touring a castle built by an eccentric inventor.

Hammond Castle, located in Gloucester, Massachusetts, was built by inventor John Hays Hammond. Holder of more than 800 patents on 400+ inventions, Hammond is best-known for creating radio control. Mentored by both Thomas Edison and Alexander Graham Bell, his research during the early 20th century laid the foundation for modern missile guidance systems and other naval weaponry.

Hammond Castle on a Rainy DAy

In addition to Hammonds prowess as an inventor, he was also an avid collector. The castle serves as a showcase of his impressive collection of Roman, medieval, and Renaissance artwork. The castle’s Great Hall also features a grand pipe organ and serves as a venue for local gatherings and even weddings!

If you’re looking for things to do in Rockport on a rainy day we would highly recommend a short drive over to Hammond Castle.


Cape Ann Museum

Another, often overlooked, Cape Ann gem is the Cape Ann Museum. Located right in downtown Gloucester, the Cape Ann Museum houses an impressive collection of art from local Cape Ann artists including an entire gallery dedicated to the art of Fitz Henry Lane.

In 2023 the museum curated a beautiful exhibition exploring the life and work of Edward Hopper who spent much time on Cape Ann.

In addition to paintings, the museum is home to some interesting maritime history of Gloucester and Rockport. You can view the original Thacher Island Fresnel Lens, the Cape Ann Dory that Alfred Johnson used to cross the Atlantic in 1876, delve deeper into the history of the fishing industry.

The museum also has a gathering space on its lower level that is used for special events and demonstrations. So, if you are looking to find a place to take shelter from the storm, Cape Ann Museum is a fantastic place to visit on a rainy day.


Capture Some Rainy Day Magic

Rockport has to be one of the most photogenic towns in New England. There are so many beautiful images of the town, but most of them are of sunrises, sunsets, and beautiful sunny days. An overcast day could provide an opportunity to capture some moody magic on the coast!

Dock Square RAiny Day in Rockport

So long as it isn’t a total wash out there are often opportunities to capture some coastal fog and angry seas that add another dimension to our seaside village. It can add an additional layer of magic to the surroundings and the quiet streets and harbors can provide the perfect pensive moment.



So looking back on Summer 2023, we try to take a positive perspective. Hey, at least none of us damaged our skin or prematurely developed wrinkles in the UV rays. And, we don’t have to stay inside, we get to stay inside and visit all of the rich cultural centers that are abundant on Cape Ann.

Hopefully, this guide will help you when you find yourself looking for Things To Do on a rainy day in Rockport, MA!

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