Rockport, Massachusetts: Great Day Trip from Boston

Day trip from Boston

Massachusetts is undeniably beautiful in summer. Areas like Cape Cod and Martha’s Vineyard are particularly famous because that’s where many of the wealthy and powerful vacation. But summer traffic and accommodation prices in those areas can be heavy and steep respectively. If you want to get better bang for your buck and time, consider driving north of Boston, to beautiful Rockport, Massachusetts on Cape Ann.

Alex & Bell Rockport

Boston to Rockport: Stop in Salem

On the way to Rockport, there’s several other noteworthy towns. The most famous is Salem, famous for the witchcraft trials in 1692. Salem is just 22 miles north of Boston and offers interesting tours, shopping, good eateries and historical significance. And these days, nobody will torture you for being a “witch!”

Rockport Beach

Cape Ann, Massachusetts

From Salem you can take a lovely coastal drive along Cape Ann on Highway 127. But if you have limited time or want to eventually continue north along the scenic New Hampshire and Maine coast, jump on the Yankee Division Highway to arrive in Rockport quicker. Just a few miles from Rockport, Gloucester is another town of historical significance. Gloucester was America’s original seaport and home to the nation’s oldest working art colony. You can even see lighthouses dating back to the 1780’s.

Rockport Beach

Rockport Massachusetts

Rockport itself is a gem, just 39 miles north of Boston, Bostonians in the know love this town. We enjoyed watching a gorgeous sunset from the beach, looking across a quintessentially rocky New England coast. Rockport is filled with an abundance of cute and historic buildings housing artisan shops, restaurants and fantastic ice cream parlors.

Many travelers even extend their trip here beyond a single day so that they can explore the town at their own pace. If you’re planning on doing the same, check out this article for suggestions on the best places to stay in Rockport.

IceCream Shop

New England takes ice cream seriously, and Rockport’s adorable Ice Cream Store is no exception. There were a lot of interesting and high quality flavors to choose from. Maple walnut is usually an excellent choice because, in New England, almost anything with maple syrup is great!

Delicious Seafood in Rockport

We enjoyed a fantastic dinner at Roy Moore’s Fish Shack, with a wonderful view of the sunset over Rockport. Their crab cakes were as good as any we’ve ever eaten. You’ll be hard pressed to top a delicious $10 crab cake main with two sides anywhere. Their fish tacos were also tasty, but the crab cakes were the highlight. Like any good seafood restaurant in the northeast, whole lobsters, as well as lobster rolls are popular items on the menu. 2022 Update: Roy Moore’s Fish Shack is temporarily closed. 


Rockport Recap

There’s much to love about Rockport, Massachusetts and Cape Ann. And if you’ve never witnessed autumn foliage in New England, it’s something you should add to your bucket list. There’s a wealth of great spots in New England to enjoy that, including the rolling hills of western Massachusetts. If you have questions or comments about visiting the region, leave a comment below!


  • Alex&Bell

    Alex and Bell originally met while solo traveling after finishing university in 2002, in Brugge, Belgium. Alex grew up in the USA and Bell hails from Australia. During our nearly 20 year marriage we've lived around the world, including spending six years living in the Netherlands and Ireland. We have traveled to nearly 70 countries and enjoy giving readers authentic and quality travel tips. Alex is an award winning travel journalist and travel planner, who also freelances for other outlets. Bell is an award winning PhD scientist who currently works for a non-profit lung cancer advocacy research organization called Lungevity. Happy travels and if you have any questions leave a comment or drop an email!

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12 thoughts on “Rockport, Massachusetts: Great Day Trip from Boston

  1. Living in Boston, we’ve been to both Gloucester and Rockport and thoroughly loved both these towns 🙂 There’s a bakery called Helmut’s Strudel shop that serves the most delicious apple strudels – we particularly remember this place! Thanks for the tip about getting to Rockport quicker – will surely keep that in mind!


    1. Thanks for the tip as well, Bharat & Supriya! Helmut’s Strudel shop sounds delicious. We’ll definitely go there next time! 🙂

    1. Thank you for the compliment on our photos! It was lovely to be in Rockport for sunset. The long days in summer make it possible to get there in the evening after a work day during the week, like this visit for crab cakes!

  2. I never made it to Rockport over the years I visited Boston. Gloucester was a favorite spot though and I had relatives living in that art colony at the time. It was fun to hang out there winter or summer.

    1. Hi Elaine. Gloucester is also really nice, and very close to Rockport. That’s really interesting that you had relatives living in an art colony there. How cool!

  3. My husband and I are flying in to Boston this September, spending a couple days there, then driving down the coast (with many stops along the way), ending at the Chesapeake Bay. When I was researching charming coastal towns, Rockport came up, but I initially deleted it from our itinerary since it’s north of Boston and we’re traveling south. Then I saw a suggestion of doing a day trip to Rockport from Boston, which would mean we’d stay overnight in Boston an additional night. In your opinion, if we’re visiting the Cape, Nantucket, Newport, Cape May, and more, is Rockport worth an extra day trip in the opposite direction when our time is limited? Or should we skip on this trip?

    1. Hi Hollie, good question. Rockport’s a lovely town, but as you will be visiting so much of the Cape and beyond, with limited time, perhaps there’s no need to backtrack. If you’re going to be taking smaller roads along your journey down to Chesapeake Bay, the driving might take longer than you anticipate, especially with traffic. Sometimes less is more and that will allow you two to get to know all the beautiful destinations you visit a little better. Let us know if you have additional questions. Happy planning and we wish you a wonderful trip!

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