Top activities to maximise enjoyment in the historic seaside town of Rockport, Massachusetts, a travel guide that came together seamlessly after I spent a hot summer time among its quirk and charm.
An hour north of Boston along the New England coast sits the charming sea village of Rockport. With a rich history and colonial influence, its colourful shacks and rows of cottages left me with a sense of whimsy.
It is small yet mighty, packed with an array of shops, restaurants, and boutiques, meandered by happy tourists. It is surrounded by the Atlantic Ocean on all sides, exposing beaches and cobalt waters bobbing with sailboats.
Built upon sunbleached rock at the tip of a peninsula, it reminded me of a European coastal town… something out of Portugal or Italy.
There, I ate and drank and spent my money on unique wares. I was entranced by the sense of age and personality. By shops plugged above clear waters with endless views of the sea. Little nooks and crannies where benches overlooked the wharf.
Below is a travel guide of the top activities in the historic seaside town of Rockport, Massachusets. Imbued with age and nautical appeal, Rockport shimmers with sunlight and treasures to ensure a memorable summer holiday.
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A travel guide to the top activities in Rockport, Massachusetts, including where to eat, shop and more
Where to stay in Rockport, MA
There is a sense of community and hospitality in Rockport, highlighted by a range of historic inns and boutique hotels.
Part of Rockport’s allure are the suburbs encircling the port. Quaint, colonial cottages line the streets with expertly maintained lawns garlanded with flower arrangements and cozy patio settings.
Check AirBnB to find what’s available, or peruse the directory on Rockport USA, the village’s official site for visitors. Most notable are the Beach & King Street Inn for its beachfront setting. And Addison Choate boutique hotel for its central location and spa-like amenities.
Although the main attraction is Bearskin Neck, I recommend spending time strolling the little streets beyond. This is where you glimpse at the life of locals, peaceful and quaint, humming with birdsong and a rich summer heat.
It would take a lot for me to leave my New Zealand home. But I imagined for a moment living here. Donning a dress and sunhat, and heading to town with a basket ready for local produce and fresh seafood. Meandering the paths down to the beach to dip my toes, and catching a coffee afterward.
Bliss.
Top Activities and things to do in Rockport, MA
Whale Watching in Gloucester
Before heading into Rockport, it’s common that visitors start their day with whale watching in Gloucester. Tourists to our core, we spent the first four hours of our day aboard the Hurricane II. We bent over the rails as a myriad of humpback whales broke through the deep waters.
To be honest, the whales were having a lazy day and seemed uninterested in entertaining a horde of chattering humans. I don’t blame them. But I enjoyed the educational elements of the voyage and the crew’s passion for protecting the magnificent creatures.
Side note: my mother assured me when she last undertook the cruise, whales breached and danced with the ship such that she got a glimpse at their sheer size. Even a pod of dolphins joined the party. What you get depends on your luck, I guess.
Culture, art, and Motif No. 1
Sufficiently sunblinded, we returned to shore and trundled on to Rockport. We parked in the suburbs outside the rush of the harbour, and that was fine by me as cottage after cottage charmed the dickens out of my camera. I clicked photos out the window as my parents debated the parking situation and my sister flung unhelpful remarks from her seat.
Strolling into central Rockport, I got my first glimpse at Motif No. 1: the famous red fishing shack at the end of the pier. Built in the 1880s, the picturesque shack attracts many artists and grace many canvases, hence its name. It’s an object of such adoration that it was entirely rebuilt after a blizzard razed it in 1978.
Rockport strongly remains an artistic hub. It hosts a variety of art and cultural events throughout the year. And gallery after gallery dot Bearskin Neck, brimming with paintings, prints, and photography… many featuring Motif No. 1.
From the locals, I gathered that Shalin Liu Performance Center is popular to catch music from well-known performers inside a beautiful concert hall. Rockport also hosts a series of performances and festivals throughout the year. You can find a calendar of events on the Rockport Cultural Arts District.
Beaches in Rockport
On top of a thriving cultural and culinary scene, a beach runs along Back Harbour, dubbed Front Beach. With its clear shallow waters, gold sands packed with people, and a backdrop of historic buildings, it reminded me of a beach you’d find in a coastal European town.
On a summer’s day, Rockport is hot and balmy. And the beach provides a refreshing interlude between shopping and eating, making the sea village a well-rounded destination for leisure and entertainment.
Where to eat in Rockport, MA
After four hours on a boat in scorching heat, my throat begged for an iced coffee. As my parents requested a table at Roy Moore’s Fish Shack (Rockport was a hive of activity by that point) my sister and I trundled down to Bean and Leaf Café.
My coffee instincts have revolutionised since living in Wellington, New Zealand. But I can safely say I enjoyed the milky latté at Bean and Leaf. And I was delighted by its pleasant interior, including the small alcove overlooking the wharf.
At Roy Moore’s Fish Shack, we ordered beers and all manners of seafood. With views of Front Beach and the wharf (again), I clicked my camera some more and sighed when buttery scallops melted in my mouth. It’s worth noting that Rockport is an active fishing port. So the seafood is local and fresh as it gets.
If you still have room in your belly, head down to the Rockport Fudgery for delectable sweets, or sample from the myriad of ice cream shops along Bearskin Neck.
Rockport is full of casual restaurants and fine dining so there’s plenty to choose from. Grab the famous lobster roll from the window at Roy Moore Lobster Company. Or perch yourself above the water at romantic My Place by the Sea.
Where to shop in Rockport, MA
Bearskin Neck is a procession of colourful shacks and storefronts, marked by vibrant signposts and fascinating trinkets on display. They balance above the water on each side, full of things I didn’t know I needed.
From pottery to handcrafted jewelry to fashion boutiques, I was surprised by the level of quality and style. I am a selective shopper these days, but I found myself swiping my card often, ensorcelled by unique goods at fair prices.
Part wares, part ambiance, the shopping experience in Rockport is the most fun I’ve had in awhile. Weaving in and out of shacks, each with more personality than the next, there was a bounce in my step. I was energised by the happy crowd, the smell of lobster and sunscreen, and the ever-present salt breeze rolling off the ocean.
At Strut Boutique, I found a blue and gold bohemian dress that had my name all over it. And across the street, Sea Bags sells totes made of recycled sails.
Further down, find the cutest wee bookshop at Susie’s Stories, a small yet teeming shed with a surprising diversity of books.
For your homewares, peruse the shelves at Alexander’s Pottery and Gifts. Or marvel at the twinkling handmade jelwery at Seaside Boutique and Beads, where I found an exquisite labradorite necklace that made me feel like I could conquer the world.
With so many sheds full of riches, the little port town felt like a treasure trove. It draws wealth from the sea in the form of food and gifts, satisfying every need. And it ensured my bag was chockful of souvenirs to take home and keep forever.
This concludes the travel guide of top activities to maximise enjoyment in the historic seaside town of Rockport, Massachusetts. If you find yourself along the craggy New England coast, do drop in for a visit and support all the local businesses in the area to ensure such a cultural hub remains thriving.
