As a City of Boston resident who does not own a car, I’ve become quite familiar with the locations outside of the city that you can visit by train. One of my favorite places to visit is Rockport, Massachusetts. If you are visiting Boston, I highly recommend taking some day trips and the train is a great way to do so.
Rockport is located 40 miles north of Boston on the tip of the Cape Ann peninsula, just east of Gloucester which many of you may have heard of from the movie Perfect Storm. Other than its border with Gloucester, the rest of the town is surrounded by the Atlantic Ocean, making it the quintessential New England seaside town to visit.

At first Rockport was part of neighboring Gloucester and was a major supplier of granite along the east coast of the United States due to the quarries in the area. In 1840, Rockport became its own town and continued to supply granite as well as become known for its fishing harbor and a popular vacation home due to its beaches.
Today, Rockport is still popular with tourist and there are lots of lobster fisherman in the area.
Fun Fact About Rockport – While the movie The Proposal starring Sandra Bullock was based in Alaska, did you know that they actually filmed it in Rockport? When you visit Rockport you will see the similarities with coastal communities in Alaska.
Getting to Rockport
Rockport is easily accessible by train from Boston. From North Station in downtown Boston, you can take the Rockport line of the MBTA’s commuter rail to the very last stop, Rockport. On the weekend, the train runs every couple of hours, with more frequent service on weekdays, especially during prime commute hours. Tickets cost $24.50 roundtrip during the week and on the weekends, they offer a special $10 weekend pass which gets you unlimited rides on the commuter rail all weekend long. For a ticket that normally costs almost $25, the $10 weekend pass is a great deal, you must take advantage of it. Check the mbta website for the train schedule.
Motif No. 1
One of the top things to see in Rockport is the most painted building in the United States and some even consider it the most painted building in the world.

Motif No. 1 is located on Bradley Wharf along the Rockport Harbor. The building that stands today is actually a replica of an old red fishing shack that was built in 1840 and destroyed during the blizzard of 1978. Due to the building’s popularity, the replica was built shortly after the blizzard. Over the years, the building got recognized as a popular painting subject due to the composition and lighting of the location. And I mean who wouldn’t want to paint this perfect New England seaside harbor scene!
Local painter Lester Hornby was the one who first started referring to it as Motif No. 1 after the students in his painting class all seemed to pick the building as the subject of their painting assignments. Now it’s become quite famous not just for painters but also photographers. On any given day in Rockport, you will see multiple people snapping photos of the building. While the view in the photo above is definitely the money shot, I highly recommend getting a view of it from all different angles while walking around Rockport.


Bearskin Neck
As the town of Rockport was known for its fishing industry, the harbor was the focal point of town. This commercial harbor has turned into the main tourist attraction in Rockport and is called Bearskin Neck.
You may be thinking, that’s a strange name for a harbor area and I agree with you. Of course, there are multiple theories on how this name came to be. The most popularly accepted reason is the name simply came from a bear that was caught in the tide and killed back in 1700. I personally prefer to go with the more interesting explanation. Years ago, a local man was attacked by a bear by the harbor. He ended up fighting the bear and eventually winning. He skinned the bear and left the bearskin out on the rocks. The fisherman coming into the harbor saw the bearskin and ended up giving the area the name Bearskin Neck. There is even a sign over one of the stores, The Pewter Shop, which depicts the local man and the bear. You can somewhat see this sign on the red building in the photo below.

Bearskin Neck is where you will find many shops and restaurants. The street gets busy with many pedestrians and also the occasional car driving down the street, so stay alert while walking in the street and keep an eye on the little ones. The shops range from your typical souvenir shops to a general store to one-of-a-kind shops with unique gifts to art galleries.
One of my favorite shops is the Rockport Candle Company and I always make sure to buy a new calendar each time I visit. I noticed the most recent time I was there that you can even make your own candle, which is always fun to do.


Many of the shops are family run businesses, some of which have been around for quite some time. The Pewter Shop has been in business since 1935, making it the oldest shop in Rockport. All the pewter they sell is made onsite.
I don’t know about anyone else, but I always work up quite the appetite while shopping! There are plenty of food options available in Bearskin Neck to help satisfy that appetite. From quick bites to sit down restaurants, there is plenty to choose from. Here are just a few great food options:
- Seafood – Being a coastal town, there are many options for fresh seafood, and you can find it on the menu at most restaurants. There are also plenty of restaurants that specializes in fresh seafood. The Fish Shack and Roy Moore Lobster Company are two of the more popular spots.
- Waterfront Dining – On a nice day, it’s always a good idea to have a great waterfront view while enjoying your meal. My Place By The Sea and 7th Wave Restaurant are two great waterfront dining options.
- Ice Cream – On a summer visit, ice cream is a must! The Ice Cream Store is my personal favorite and judging by the line every time I’ve been there, its other people’s favorite as well.


Rockport Breakwater
If you walk thru Bearskin Neck towards the water to the very end you will come to Rockport Breakwater. The breakwater is 1/8 of a mile long and it’s a great little walk with spectacular views of Rockport, the harbor and the ocean.

While the breakwater has been rebuilt in 2015 and now features mainly flat rocks making it easy to walk to the end, you should still make sure to wear proper footwear. Make sure to hold your belongings tightly as I did see someone’s insulated water bottle fall out of their hand and thru a hole between the rocks down into the ocean. It’s definitely a fun activity for the whole family to walk out along the rocks.

Once you get to the end, you are at a great spot to sit and relax for a bit. Also, from the end you get a nice view of the Straitsmouth Island and its historic lighthouse. There have been three lighthouses on the island, the first built in 1834 and the final one built in 1896. The lighthouse was added to the National Register of Historic Places in 1987. Straitsmouth Island and the lighthouse are now part of the Massachusetts Audobon Society as a wildlife Sanctuary.

Kayak and Boat Tours
If you would like to visit Straitsmouth Island, a great way to do so is by kayak. North Shore Adventures has kayaks for rent as well as many different tours available, including:
- Island Kayak Tour – This tour will take you 1 mile out to Straitsmouth Island and additional 1.5 miles to Thatcher Island further out in the ocean with stops on the islands.
- Seal Kayak Tour – This tour goes to a outcropping of walks 2.5 miles from Rockport to see seals and birds in the area.
- Coastal Kayak Tour – This tour is great for beginners who want to stay a bit closer to coast.
- Evening Kayak Tour – This tour is great for those really hot days as it will be cooler in the evening and depending on the time of year, you might catch the sunset on this tour.

If you prefer to not have to do the work of kayaking, why not take a tour on a lobster boat! Captain Jim’s Rockport Seaventure offers tours on its lobster boat, First Lady, on the weekends and holidays. Not only will you learn more about Rockport on this boat tour, but you will also learn about catching lobsters. I haven’t done this tour just yet, but it’s definitely on my bucket list, what a unique experience!
Beaches in Rockport
Being on the coast there are many beaches in Rockport including a couple within walking distance of downtown. While there are many beaches in the area that are much larger, these beaches are still a great alternative if you are looking to spend a bit of time at the beach while visiting Rockport by train.

The first beach you will come to walking from downtown Rockport is Front Beach. This is the best beach if you are looking to sit in the sand and enjoy the warm weather. The beach is staffed with a lifeguard making it a good choice if you are at the beach with young ones. Even if you don’t plan on spending time on the beach, I definitely recommend taking a walk by the beach as it’s pretty beautiful to see.


If you continue walking past Front Beach, you will come to Back Beach. This beach is much more rocky than Front Beach and not one for laying on the beach. Back Beach is actually known for its scuba diving. This is also a great beach to walk along or just sit on the larger rocks overlooking the beach and enjoy the views.


Rockport definitely has plenty to keep you busy for a day trip from Boston and all is just a quick walk from the train station. This is one of my favorite places to visit outside of the city of Boston and a must visit for anyone visiting Boston.

Beyond the Miles Travel would love to help you plan a trip to Boston with Rockport as part of your itinerary, contact us today.
This article is now featured on GPSmyCity. To download this article for offline reading or create a self-guided walking tour to visit the attractions highlighted in this article, go to Walking Tours and Articles in Rockport.
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Looks like the perfect spot for a day trip!
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I love Boston, there is so much history and lots of things to do. I’d love to go kayaking there!
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I really want to visit Boston and now Rockport! The Proposal is one of my favorite movies and I had no idea it was filmed in Rockport.
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I’ve never been to Boston but now I really want to go! This Rockport day trip sounds so fun!
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Your blog post has provided me with the inspiration and guidance I needed to plan a memorable day trip to Rockport. I appreciate the effort you put into sharing your experiences and recommendations. Keep up the excellent work, and thank you for being a valuable resource for travel enthusiasts like me!
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Looks like the place is worth visiting. Surely would plan to travel soon.
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I have never been to Boston; on my list of states to visit. Your blog is helpful for future reference. Pinned.
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Pretty pictures, awesome places to visit if you’re in Boston..
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This is such a helpful post. I’ve never been to Boston when visiting America and I love train travel! Bearsking Neck looks like my kind of place!
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Great post on day trips from Boston! I love the idea of a Kayak Tour, and think I would enjoy it! Thanks for sharing
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Kayak tours are such a great way to see an area by the sea
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This guide to Rockport is so detailed and inspiring! As the solo female traveler behind Life of a Journey, I love finding train-accessible day trips like this—it makes exploring without a car so much easier. Motif No. 1 and Bearskin Neck sound like must-sees, and now I’m adding Rockport to my New England travel list. Thanks for sharing such a helpful breakdown!
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