I’ve spent more than two decades visiting Martha’s Vineyard, even though I live in another popular New England destination: Newport, Rhode Island.
The island attracts everyone from famous musicians like Carly Simon to A-listers including the Obamas and Oprah Winfrey, all lured by its natural beauty, stunning beaches, and coastal charm. But during the height of summer, its allure can mean long waits at popular restaurants, pricey ride shares, and very expensive lodging.
A few years ago, I discovered Rockport, Massachusetts, for the first time, and it immediately reminded me of the Vineyard. I’ve been visiting ever since.
The smaller coastal town is only about 40 miles northeast of Boston, and just a little over a two-hour drive from my home in Newport.
Here’s what made me fall in love with it.
There are picture-perfect views around every corner
Like Martha’s Vineyard, Rockport seems straight out of a postcard with jaw-dropping views, waterside restaurants, and a classic New England harbor.
It’s known for its rocky coastline, working waterfront, storybook downtown, and vibrant art scene, much like the Vineyard. I love to check out the galleries I stumble upon (there are more than two dozen!) as I walk around town.
Rockport’s most famous landmark, Motif No. 1, is a large red fishing shack covered in colorful buoys. Perched atop a picturesque granite wharf that jets out into the harbor, it has long been referred to as “the most painted building in America.”
In the warmer months, you’ll likely see plein-air painters and their canvases around town and people like me snapping photos of the shack from every angle.
Although there aren’t nearly as many beaches in Rockport as there are in Martha’s Vineyard, the handful the area does have are easy to reach and still offer iconic New England vibes.
A popular pick is Front Beach, and its proximity to downtown makes it easy to grab breakfast sandwiches, snacks, and ice cream between sunbathing breaks.
I get to leave my car behind and explore so much on foot
Martha’s Vineyard is primarily accessed by ferry, which visitors can pay a fee to take their vehicles on.
No ferry is needed to get to Rockport. Instead, you can drive in or even take the commuter rail there directly from Boston. The ride is only about an hour, and the station is close to downtown.
Once you arrive, Rockport is a town best explored on foot.
Bearskin Neck, in the heart of the town, is dotted with weathered cedar-shingle cottages that house boutiques, mom-and-pop stores, candy shops, galleries, and plenty of spots to enjoy creamy New England clam chowder and lobster rolls.
The Ice Cream Store may not have a very creative name, but it’s my favorite place to grab a cone.
The area can feel touristy and draw a crowd, so I prefer visiting earlier in the day, but it is absolutely worth exploring.
At the end of Bearskin Neck is a crescent-shaped rock jetty. I like to walk all the way to the end to watch the boats come and go.
Dock Square is also part of Rockport’s pedestrian-friendly downtown and a great place to wander and grab a bite to eat. After, I peruse Main Street for a casual stroll; it’s the best way to see the architectural detail on historic churches and early 19th-century houses and buildings.
About a 15-minute walk away is the Granite Pier, which offers panoramic views of Sandy Bay and the Atlantic Ocean, plus you’ll see plenty of seabirds.
The pier is also where you can catch a seasonal launch boat to Thacher Island, about a mile offshore. I’ve saved it for my next visit, when I’ll explore the island’s 3 miles of trails, view historic lighthouses, and hopefully, see lots of wildlife.
I stay at cozy inns that capture small-town New England charm
Similar to Martha’s Vineyard, you won’t find major national hotel chains in Rockport. Instead, there are friendly inns and bed and breakfasts, which really give your stay a personal touch.
They also add to the town’s authentic character. Plenty have cozy porches ideal for curling up with a good book.
Fortunately, I’ve found accommodations here to be much cheaper than the hotels in Martha’s Vineyard.
The last time I visited, I stayed at Emerson Inn by the Sea. It’s one of the oldest seaside inns north of Boston, and I loved that I was able to open all the windows in my room and be lulled to sleep by the sea air and lapping waves.
Its location gave me easy access to the Atlantic Path, a 1-½-mile footpath dating back many years.
It traces the rocky coastline, and I liked that some parts of the path required me to make my way over and under boulders. The large, flat rocks also convinced me to turn off my phone, take a seat, and just take in the quiet of the seaside.
Another morning, I grabbed my coffee and walked down to Pigeon Cove, a small harbor on the north side of Sandy Bay filled with working fishing boats.
Old and tiny fishing shacks full of equipment lined the wharf, and I was up early enough to see the crews loading up and heading out to land the day’s catch.
Plus, Rockport’s location on Cape Ann makes it easy to explore other quaint towns nearby
Gloucester borders Rockport and is America’s oldest seaport. Full of the best local seafood, cool history, and a quaint downtown, it’s worth a visit.
Similarly, Manchester-by-the-Sea, Essex, and Salem are all within a 30-minute-or-so drive of Rockport and are classic New England towns packed with personality and spirit.
Although Martha’s Vineyard is a spectacular destination, Rockport offers similar coastal allure with harbor views, walkability, fewer crowds, and less expensive accommodations — no ferry required.
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