I love visiting charming New England seaside towns during the off season, and a few days stay in Rockport, Massachusetts didn’t disappoint. Seriously, by taking a wintertime visit to Cape Ann you can truly appreciate quintessential New England without the crowds. The highlights of a girls’ getaway with my sister were soaking up the natural beauty of the coast on a relaxed timeline. We enjoyed up the harborside area of Rockport on foot and explored Gloucester with short car-ride excursions. 

Our intention with staying in Rockport was the lure of the harborside village to stroll around while finding accommodation within easy walking distance. With fingers crossed, we hoped enough local businesses would be open to keep us entertained and occupied. Success on all accounts as we found a lovely two-bedroom Airbnb and many shops were open for ample retail therapy.

Rockport’s Iconic Motif No. 1

World-famous Motif No. 1, located on Bradley Wharf, is claimed to be the most-painted building in the United States. Don’t be fooled thinking it’s just a simple fishing shack; the little red building’s history runs deep. Built in 1884 when the fishing village was emerging as an artist colony, the structure soon became the favorite subject among painters. The composition of the rustic dark red set against the backdrop of the harbor and blue sky, has made it a maritime icon of Rockport.

American Painter Lester G. Hornby, who taught students in Paris in the winter and Rockport in summer, was said to urge them to find artistic inspiration from local scenery. While his Parisian students found a variety of subjects or motifs, his Rockport students were primarily attracted to painting the red shack, obviously their “number 1 motif.” So, there you have how it got its name!

Another interesting piece of the little shack’s history is that the building isn’t the original. Destroyed by the Blizzard of 1978, the fishing shack was rebuilt as an almost-exact replica that same year.

Motif No. 1 has also appeared on the big screen in the “Proposal” that took place in Sitka, Alaska but was actually filmed in Boston and the North Shore. In “Finding Nemo,” the red shack appears in a picture hanging on the wall in tribute of director Andrew Stanton’s hometown.

Shopping in Rockport Harbor Area

We spent a half day partaking in retail therapy in the Rockport harborside area along Pleasant Street and Bearskin Neck. We engaged with friendly locals as we shopped and got acquainted with the area. The photos below provide a sampling of boutiques, gift shops and galleries we enjoyed.

We couldn’t miss out on this shop selling jewelry, accessories and women’s apparel that hones in on Massachusetts’ “wicked good” colloquialism in its name! Visit on Facebook.

Susie’s Stories Bookstore is a sweet shop to browse. Visit on Facebook.

Family-owned and featuring items from local artists, the Pewter Shop, a Rockport staple since 1935, has something for everyone from jewelry, home décor, ornaments and kitchen goods.

Kaihlanen Galley is a fun place to browse for interesting, whimsical art. I wish I had taken a photo of artist/owner Lauri Kaihlanen along with his self-portrait on display. Visit on Facebook.

The Country Store caught my eye especially with the wig heads from the second-floor window looking down at shoppers! Visit on Facebook.

The Art of David Arsenault is a gallery worth stopping in for pieces inspired by local scenery.

More Sights in Bearskin Neck Area

If music is your thing, the Shalin Liu Performance Center, located at 37 Main Street, is considered a hidden gem for music venues in Massachusetts. A colleague talked about the impressive sweeping views of Rockport’s Sandy Bay, so I wanted to check it out for myself. Learn more about Shalin Liu Performance Center and upcoming events.

A mini gallery on Pleasant Street displays a Judi Rotenburg piece. Ironically, we saw daffodils in real life already sprouting just around the corner in February.

Pause to read this sign for a quick history lesson on Rockport.

The lighthouse you see in the distance from the tip of Bearskin Neck is Straitsmouth Island Lighthouse. It was built in 1835 and marks the entrance to Rockport Harbor.

Take a Drive for More Rockport Sites

We explored Rockport and surrounds on a sunny, clear day by hopping into the car. Everything is a short drive away. Here are some stops you may enjoy to get out of the car and stretch your legs to snap some photos!

Halibut Point State Park: Open year around from 8 am to sunset, Halibut Point State Park offers visitors the beauty of an enormous granite quarry facing the Atlantic Ocean. Explore the trails, tide pools and rock ledges. On a clear day, you can see Mount Agamenticus, Maine and the Isles of Shoals, New Hampshire. Learn more.

Views of Ipswich Bay: In our travels around Cape Ann, we stopped at the beach next to the Lobster Pool to take photos on a windy morning.

Old Granite Pier: Constructed in 1840, Granite Pier and is one of Rockport’s four harbors. The other three are Rockport, Pigeon Cove and White Wharf. While here, get some great snapshots of Rockport Center from the upper level. Stand above the beach side facing the ocean and take moment to listen the sounds of the waves washing over the beach rocks below. Sensory moment!  

The Paper House: While not open until spring, out of curiosity (akin to seeing the biggest ball of twine!), we decided to do a drive-by to check out this local attraction. The framework, roof and floors of the Paper House are constructed of wood while the rest is made of layers of newspaper, glue and varnish. Built by Elis Stenman, a mechanical engineer who designed machines that make paper clips, the house was completed in 1924. Learn more about this attraction from a question-and-answer piece from his grandniece Edna Beaudoin.

Things to Do in Gloucester

Eastern Point Lighthouse

Don’t be deterred by “private road” signs when headed to see the historic Eastern Point Lighthouse, which was added to the National Register of Historic Places in 1987. Visitors are allowed to drive to the lighthouse. If someone is at the gate, just tell them you’re going to the lighthouse. There is a parking lot managed by the Massachusetts Audubon Society as part of the Eastern Point Wildlife Sanctuary.

The grounds are closed but you can view the lighthouse from the beach. The light, first lit in 1832, was automated in 1985. It is still an active aid to navigation and provides housing for the Coast Guard.

Check Out a Medieval Castle

While cruising around Gloucester, we decided to stop by Hammond Castle hoping we’d see some of the building from the parking lot. We peeked around but didn’t want to trespass; we were able to see some of the castle and grounds through the trees. Take a virtual tour. The museum is re-opens in April. See visiting hours. Below is a photo you’d only see from the ocean!

Pavilion Beach and Sea Glassing

When in the North Shore, you do what beachcombers do: Go sea glassing! We dropped by Gloucester’s Pavilion Beach, viewed the famous “greasy pole” and tried our luck finding treasures in the sand. We found some white/clear, green and brown beach glass to add to our collections. Visit this Boston Magazine post that suggests top places to find sea glass in Massachusetts including Pavilion Beach and other North Shore spots in Rockport and Marblehead. 

Where We Ate While Visiting Cape Ann

Visiting during the winter months, we found that many Rockport restaurants were opened over for the latter part of the week and some were closed on Monday and Tuesday. That didn’t deter us for a Sunday-to-Tuesday visit because Glousester was just a 20-minute drive away with plenty of dining options.

We enjoyed lunches and dinners out, and here are the restaurants we tried and would recommend:

• Fleur Cuisine, is located at 1-T Wharf, Rockport, and literally steps from our Airbnb. We had salads and a few glasses of wine here on a Sunday night. We loved the food and atmosphere; highly recommend. In the warmer months, enjoy dining al fresco with a harborside view.
• The Causeway, located at 78 Essex Avenue, Gloucester, is where we had lunch on our first and last days coming and going to the North Shore. It’s a casual place on a main road offering BYOB. Amazing food, including seafood, pasta dishes, sandwiches and salads, that we thoroughly enjoyed. Twice! 😊
• Azorean Restaurant and Bar, located at 133 Washington Street, Gloucester, offers flavorful and wonderfully spiced Portuguese food. The décor is unique and comfortable with an old-world European charm. We had lunch in the bar area and joined many locals having lunch. Try the fava beans and garlic shrimp appetizers!
• George’s Restaurant and Bar, located at 178 Washington Street, Gloucester, is open daily offering breakfast, brunch and dinner. My grilled chicken dinner with baked potato and roasted broccoli hit the spot!

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