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Winter In Rockport – 10 Great Things To Do

Winter In Rockport – An Empty Amusement Park That’s Worth a Visit

After the leaves have turned, the harvest festivals ended, Santa’s sleigh departed, and resolutions broken. After the wreaths, trees, and lights have been removed, we New Englanders are left face to face with the icy glare of old man winter.

Rockport MA Winter

On the coast of Cape Ann, in the village of Rockport, these feelings of introspection are seemingly amplified by the stark contrasts between the congestion of Summer and the solitude of winter.

Despite the frigid temperatures and seclusion, Winter in Rockport provides a tranquil respite that is often overlooked.

The quiet streets provide room to breath and give this quaint village the feeling of possibility and wonderment similar to that of an empty amusement park. It provides an opportunity for meaningful connection with the local landscape, local businesses, and local characters alike.

Let’s take a closer look at what makes Winter in Rockport so special.


Stunning Scenery That’s Accessible

There is no question that Rockport is one of the most scenic towns in all of New England. It’s like an inspiration IV drip for artists. The coastal village has drawn painters, writers, photographers and creative types for generations.

The iconic inner harbor, the craggy shorelines, Motif #1, stunning sunrises, and ever-changing light provide a perpetual flow of artistic inspiration.

When visiting Rockport in the winter you’re no longer forced contend with the throngs of tourists jostling for parking, the perfect lobster roll, or coveted beach real estate. You can take in the charm and character of the village and surrounding landscape in peace.

The beaches and coastline still offer stunning scenery and the winter can really put the majesty of mother nature on full display. You can take an invigorating walk through Halibut Point or the Headlands or make your way out to Long Beach, Front Beach, Wingaersheek or Good Harbor and inhale that crisp cold and air and almost feel guilty that you have the space to yourself.


Celebrate The Arts On The North Shore

There is an abundance of art on the north shore of Massachusetts to experience and enjoy. Rockport, has over 30 galleries showcasing the work of over 400 artists. You could literally take an entire day just exploring the galleries and shops in town.

To help set you off on the right foot, here are 7 of our Favorite Rockport Art Galleries.

In addition to painting and sculpting, the north shore has some fantastic venues for live performance including the Shalin Liu Performance Center in Rockport.

Shalin Liu Rockport MA

This stunning 330 seat venue overlooks Sandy Bay and has an impressive musical draw. This year the Shalin Liu brought in musicians such as Grace Kelly, Branford Marsalis, Arlo Guthrie, John Scofield, Marc Cohn, the Quebe Sisters and many others.

Check out their musical calendar here. https://www.rockportmusic.org/

The Cabot Theater, in Beverly, is another north shore treasure. The Cabot dates back to the 1920’s and recently underwent a loving restoration. Musical acts such as John Mayall, Jake Shimbukuro, Del McCoury, Chris Botti, Little Feat and many others have graced the stage. You can take a peek at the upcoming event lineup here: https://thecabot.org/events/category/concerts

The Cabot Theater
286 Cabot Street
Beverly, MA 01915


Bring Fido To The Beach – And Let Him Frolic Off Leash

In the winter, the city of Gloucester allows you to bring your furfriends to Good Harbor and Wingaersheek beach. In Manchester, you can bring your doggos to Singing Beach. On even numbered days you can let them off leash at Good Harbor and on odd numbered days you can let them off leash at Wingaersheek.

Dogs On Beach Gloucester MA

If you need a fun winter pick-me-up this is the a good one. You get some fresh ocean air and exercise in a beautiful setting. Plus, some beach time is guaranteed to bring a smile to both Fido’s face and yours.


Indulge In Some Delicious Cuisine

Just because the mercury has dropped a little lower doesn’t mean that you can’t indulge in some delicious local seafood. Restaurants like Feather and Wedge, Roy Moore’s Fish Shack, and The Blue Lobster have you covered year-round. They will satisfy your crustacean cravings as well as providing a variety of creative culinary creations that will surely hit the spot.

In addition, there are many fantastic dining options down the road in Gloucester (Duckworth’s Bistro, Passports, Minglewood Harborside, and Tonno). If you’re up for a short trip down to Beverly or Salem you could hit up Turner’s Seafood in Salem and the new restaurant, Frank, in Beverly.

For some additional information check out this list of our 9 Great Restaurants Near Rockport.


Hit Up The Local Museums

The north shore has a fantastic array of high-caliber museums to explore. In Rockport you can take in an exhibition at the Rockport Art Association. Now in its 98th season, the art association provides a variety of installations , educational workshops, demonstrations and lectures.

Rockport Art Association
12 Main Street
Rockport, MA 01966

The Peabody Essex Museum, down the road in Salem, is truly a world class museum. The light filled atrium, café area, and variety of installations make for an enjoyable and enriching visit, no matter your taste in art.

Peabody Essex Museum
161 Essex Street
Salem, MA 01970

Founded in 1873, the Cape Ann Museum in Gloucester is another great museum that focuses on the local history of this fishing port. The museum houses the largest collection from marine artist, Fitz Henry Lane, has many works from talented Cape Ann artists, and some fantastic exhibitions such as the recent Winslow Homer Exhibit.

Cape Ann Museum
27 Pleasant Street
Gloucester, MA 01930


Strikes and Gutters, Ups and Downs

Embrace your inner Kegler at Cape Ann Lanes bowling alley in Gloucester, MA. Cape Ann Lanes is a classic candlepin bowling alley that has been family owned and operated since 1959. The bowling alley was recently acquired and restored by new owners Caitlin and Nic Pszenny who just added a beautiful new brew pub to the location.

Cape Ann Lanes
53 Gloucester Ave
Glocuester, MA 01930


Take A Day Trip Down To Salem Or Beverly

Another great reason to visit Rockport In Winter, or any season for that matter, is that it is great outpost for all of the local destinations. For example, Salem and Beverly, MA are only 15-20 minutes away and have a plethora of activities available in all seasons.

Salem, of course, is famous for its history of witchcraft. While things are crazy in the fall, Salem is a great place to visit in the winter when the streets are a little less crowded. Some attractions in town include the Peabody Essex Museum, The Salem Witch Museum, The House of Seven Gables, Ghost Tours and a variety of adorable shops.

If you get hungry we would recommend Turner’s Seafood, Opus, Howling Wolf Tacqueria and Sea Level Oyster Bar.

Beverly is also a new up and coming city on the north shore that is worth a visit. With a bustling downtown that includes a variety of shops, boutiques, the Cabot Theatre, Larcom Theatre and a variety of great restaurants it’s definitely worth a stop.

A few restaurants worth checking out are the Beverly Depot, A&B Burgers, Bonefish Harry’s and the all-new Frank (owned and operated by James Beard winner,f and former L’Espalier proprietor, Frank McClelland).


Shop Till You Drop

Ok, so Christmas is in the books but you still have that shopping bug. We get it. Retail therapy is a real thing, even if it isn’t covered by your health insurance.

Not to worry Rockport has you covered. You can browse all of the local shops down in Dock Square, on Main Street and on Bearskin Neck. Although some shops close for the season in the fall and early winter, there are still many shops that remain open year-round.

You can also venture into Gloucester and even up to Newburyport if you’re looking for some additional coastal shopping. If you head up to Newburyport we recommend getting a delicious seafood lunch at Brine. They have some great oysters and outstanding crudo!

You can take a closer look at some of the fantastic shops in Rockport, MA in our article: 12 Great Shops in Rockport, Massachusetts


Check out The Local Bookstores

People in Massachusetts are Wicked Smart and love to immerse themselves in books. The north shore of Massachusetts has some fantastic bookstores that are a bibliophiles paradise. From Manchester By The Book in Manchester By The Sea to Dogtown Books in Gloucester and Art Longwood Books in Rockport there are many fantastic places to visit.

Rockport MA Bookstore

Each store is unique and has their own catalogue, but all are worth a visit. These 3 stores carry a variety of used books, but if you’re looking for new books you can check out the Bookstore of Gloucester. It’s a great way to support local businesses that have had an uphill battle with the Amazons of the world.

For more information on local bookstores check out our article on 5 Great Independent Bookstores on Cape Ann


Knock Back A Few Microbrews

Gone are the days when Sam Adams & Harpoon were the only game in town. It’s hard to believe but there are now over 100 breweries in Massachusetts, and some great ones at that. Names like Tree House Brewing in Charlton, Trillium (seemingly all over Boston now) and Mystic in Chelsea have taken on legendary status. But the north shore of Massachusetts has its fair share of great breweries to explore!

A few great places to grab a brew and go on a brewery hopping tour (this should really be offered!) include: Notch Brewing in Salem, True North Ale Company in Ipswich, Bare Wolf in Amesbury, Great Marsh Brewing in Essex, Cape Ann Brewery in Gloucester, Channel Marker Brewery and Gentile Brewing in Beverly, and keep an eye out for the new Rockport Brewing Company, right here in Rockport, Massachusetts.

We hope that you found our list of 10 things to do in Rockport in the Winter to be helpful! There is so much to explore on the north shore of Massachusetts that we really have just scratched the surface. The team at our Rockport MA Hotel is always happy to answer any questions and help point you in the right direction! We hope that you get out and make the most of the New England winter. 

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