The Old Glory in Seaside Rockport, Massachusetts

Cape Cod’s charm reigns supreme in the summertime off Massachussetts’ coast, but as the leaves fall come September and the skies grow gray, there’s a homespun feeling of coziness to chase around the north shore of the state. Salem sees its time of mischief and magic around Halloween, and in November, the quiet and intimacy of fall shines best in the small town of Rockport. The village of 6,000 inhabitants seems quiet, with a modest history of fishing and granite mining, but today this old town thrives under the guise of an artistic hub for creatives to enjoy beauty among its bones.


Rockport in the colder months still remains a sunny spot on the coastline of Cape Ann, and it’s a place to run to when the sounds of the sea and small town hospitality are just what you’re missing on a fall or wintry day. The furthermost point after Cape Cod’s Provincetown, the beauty in reaching Rockport by car is that it’s not en route or a stop on the road– it’s the end of the line, where the land of the New World meets the gray shores of the Atlantic’s vast waters. It’s a harmonious state of mind, best preserved at the edge of the world. The anchored sailboats, the shingled and weatherbeaten buildings, and that smile you see on almost everyone you pass, from the teenage servers at My Place by the Sea, to the charming owner of Rockport Candle Co. as she excitedly tells you about the latest addition to their fall scents while Motif. No. 1 stands lonely yet proudly just outside the shop’s window– gracing this picturesque town are those small feelings of kindness and endurance, that aren’t anything new around there– it’s just how it’s always, and will always be.

Read more about the distinguished places within Rockport that you must absolutely see for yourself in our little guide below!


My Place By the Sea

A charming little hut that serves pristine views of the Atlantic and flavorful takes on classic seafood dishes. The award-winning restaurant has been praised by modern pop stars and regional legendary publications like Yankee, but despite its notoriety My Place remains a humble and genuine place. From the clam chowder and even the grilled chicken brie sandwich, what truly makes dining here delicious is the locally-sourced food for an authentic taste of the North Shore.

Visit today at 68 Bearskin Neck, Rockport, MA 01966


Bearskin Neck

This small jetting landmass along the furthermost point of Cape Ann remains the heart and soul of the little town. The houses that line the main street out to the sea and back towards the rest of the town are filled with shops and confectionaries, but in the beginning there was a strip of land where a drowned bear washed ashore, giving its namesake, and leading to one of northern Massachusetts’ thriving shipbuilding harbors for 150 years.

Learn more at

Toad Hall Bookstore (Granite Savings Bank)

Although Mr. Toad’s closed its doors earlier in 2017, the building that once housed the town’s bookstore was also the official stronghold of the local Granite Savings Bank in 1926.

See the building at 47 Main Street, Rockport MA 01966

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The Paper House

If you were wondering why, then yes– the entire house is made from paper! In 1922, mechanical engineer Elis F. Stenman crafted this house purely as a hobby. From the piano and furniture to even the curtains, the home remains a local gem and monument to the artistic innovations of the town.

Visit at 52 Pigeon Hill Street, Rockport, MA 01966

Rockport Candle Company

Rockport natives in love with the classic scents inspired by the sea and smalltown charms first opened the doors of the Rockport Candle Company in 2016. Comforting scents range from drinks by the fireside and quarry walks, to more unique and personal curations like Cape Ann Christmas and Sweet Buttered Lobstah!– the later smelling sweetly of butter and lemon for unexpected zest.

Visit the shop at 45 Bearskin Neck, or online at

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Shalin Liu Performance Center

Local organization Rockport Music hosts many of its fine seasonal performances within the mesmerizing hall of the Shalin Liu Performance Center. The impressive hall, opened in 2010, celebrates the sounds of chamber music and more, all within view of the ocean that can be seen by the grand wide window that lies behind the main stage. Hosting famous acts through the decade, the center’s shining moment comes in as the annual Rockport Chamber Music Festival held every summer.

See their schedules at

Motif No. 1

Widely regarded as the most often painted structure in America, there is a strong yet welcoming beauty to this old fishing shack nestled on the wharf of Bearskin Neck. Painstakingly preserved by the town by keeping away overhead wires and signs and reapplying a special weatherbeaten-looking paint to its exterior, the motif remains a beacon of comfort and maritime heritage for all of New England.

See the Motif for yourself at Bradley Wharf, Rockport, MA 01966


The Fudgery

You can find seaside favorites like saltwater taffy here, alongside good ol’ fudge that cannot be rivaled elsewhere in the town. Situated at the edge of Tuna Wharf on Bearskin Neck, the beautiful gray building of the Fudgery even had a cameo in the 2009 film The Proposal, where Rockport featured as the Alaskan town of Sitka!

Taste local delights at the Fudgery on 4 Tuna Wharf, Bearskin Neck

Or see their selections at

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