Rockport on a Blustery Day

Enjoying Rockport Massachusetts After the Summer Ends


We love traveling in the off season. After summer is over, after the throngs of tourists thin out and a chill wind whips up the waves that crash spectacularly into the rocky Cape Ann shores, it’s still not too late to enjoy Rockport.















During the summer, you may look forward to a short boat ride and a picnic at Rockport’s famous twin granite lighthouses, rising 124 feet above Thatcher Island and guiding ships safely around the cape for more than 150 years. For higher adventure, summer visitors can enjoy whale-watching boats and those of us who are land-bound can enjoy hiking the scenic trails of Halibut Point State Park. But a visit to Rockport on a wet late-autumn weekend calls for staying in the town, exploring shops and galleries, and enjoying a cozy bed at a Rockport B&B. On our recent visit to Rockport, we stayed close to Rockport Harbor, hopping from shop to shop and having a great time.

Rockport Harbor is the location of a famous red fishing shack festooned with lobster pot buoys known as “Motif Number 1”. An artist’s colony established in the mid-1800’s tended to make the building a frequent subject of paintings, so frequently that it is considered the most frequently painted building in America. The building, sitting prominently on the end of Bradley Wharf, was destroyed during the infamous Blizzard of ’78 and then rebuilt, technically making it a replica but no less iconic.

Over the years, the fishing shacks and maritime businesses have largely been taken over by shops and art galleries.

Bearskin Neck meets Upper Main Street at Dock Square, not exactly a square, but a junction that at least makes a good reference point. We enjoyed coffee at the Nine Lives Café, tucked into a corner at the square. Nine Lives features “Fair Trade” coffees and teas, sourced so that the coffee bean growers get better pricing for their work. The cozy café has a couple tables for enjoying wholesome baked goods, window seats for relaxing, perhaps with a book from their little trading library or playing one of their children’s games, making it a nice place for hot coffee or hot chocolate before scurrying along onto Bearskin Neck.

rockport_18Over the years, the fishing shacks and maritime businesses have largely been taken over by shops and art galleries. Some of the shops focus on t-shirts and nautical knickknacks, as would be expected in a New England coastal town popular with tourists. Some of the shops have distinctly Asian merchandise.

We sought out for the shops that focused on the artisans crafting specific media – in one case, the Village Silversmith, right on the square. My wife’s taste in jewelry tends toward silver, and when she saw that not only did they create jewelry with gemstones, but also with fossils so it was hard to get her to choose one necklace over another.

rockport_08 Farther on the Neck, we found Bearskin Neck Leather, with high-end leather goods, like Minnetonka moccasins and Taos Footwear boots, along with purses, belts, and hats. We also found the Pewter Shop with fun bangles and charms and Earth’s Treasures with bright colors and beads in its jewelry.

Of course we found the shops with fudge, sweatshirts, and refrigerator magnets, then we sought out the galleries and studios. Art is subject to personal taste, so it’s good that there are so many galleries. Most tend toward landscapes – the kind of work you’d expect where Motif Number 1 is a regular feature of inspiration. Look for the galleries all along Main Street and all the way up Bearskin Neck, sometimes shoulder-to-shoulder with other galleries.

Of course we sought out food too. Right at the end of Bearskin Neck is My Place by the Sea, a fine dining restaurant focusing on the bounty of the sea. Our amazing meal started with clam chowder and the chef’s daily seafood tasting – a trio of delicious appetizers, then continued with a delicious salad with roasted beets and heirloom tomatoes with Maytag bleu cheese. For our entrees we enjoyed swordfish with spicy pecans and béarnaise sauce and a pan roasted cod with braised leek sauce. When the weather is rough, the outdoor and upstairs seating is closed – and if you wait too late in the season, the restaurant closes for the winter.

rockport_19Roy Moore Lobster Company is another great choice for dining. There are actually two locations – within 500 feet of each other. First is the very casual, rockport_20order at the counter and eat outside on the patio restaurant – on a windy, cold, wet weekend only the bravest of diners attempt dinner there. If it’s that cold, the Roy Moore Lobster Company right on the square is a warmer choice. That more traditional restaurant is sometimes called “The Fish Shack”, despite having the Roy Moore sign out front. There we enjoyed mussels and lobsters, a happy an attentive staff, and a family dining atmosphere.

For our home base, we stayed at the 7 South Street Inn, a very well-appointed B&B a short stroll from the Square. The inn was built in 1766, before the Revolutionary War, and added onto since, giving it eight guest rooms, each with its own electric fireplace, bathroom, and amazingly comfortable bed.

Innkeepers Deb and Nick Benn have created a very welcoming atmosphere and serve creative breakfasts. Breakfasts each morning start with fresh fruit and a sweet bread, a glass of fruit juices, and then the entrée of the day like a croissant eggs benedict with country ham, baby spinach, and hollandaise sauce, and of course plenty of hot coffee. We were also very happy to see that Deb and Nick provide gluten-free options for those visitors with sensitivities to wheat.

rockport_24During the summer, the Inn has a pool for their guests, and it’s a very short walk to Davis Park, overlooking the shoreline, and the Headlands overlooking the Harbor. But during a cold and blustery evening, it’s a lot more fun just to snuggle up, enjoy the fireplace, and remember the great food and the shops and galleries of Rockport.

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